Discover Luxurious Resorts in Islamorada, FL

Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot fishing pier. Each guestroom includes dark hardwood furniture and a balcony with views of the resort. Guests can watch movies on the 42-inch flat-screen TV with DVD player or browse the internet with free WiFi. An in-room safe and coffee maker are also provided. Adult and family-style swimming pools can be enjoyed at the resort. Additionally, a fully equipped fitness center, 6 tennis courts, and a full-service watersports facility are open to guests. Three restaurants and a tiki bar are located on-site at Cheeca Lodge & Spa. Atlantic’s Edge offers tropically-inspired cuisine amid a classic décor while Nikai Sushi Bar & Restaurant serves nigiri, sashimi, and more. Downtown Key Largo is a 20-minute drive from Cheeca Lodge & Spa. Long Key State Park is 13.7 miles from the resort.

- "It was a wonderful experience." - "I was visiting for my birthday and it was one of the most beautiful places I’ve ever visited. The people were very welco" - "Took my 20-year-old niece with me I don’t think it’s a great place for younger kids" - "Did enjoy" - "Great romantic place to stay with gorgeous views from everywhere." - "Great facility warm and informative employees" - "Spectacular but make sure you’re not next door to any noisy dogs!"

Luxury resort on the beach, with 3 outdoor pools
Spend the day relaxing at Cheeca Lodge & Spa's private sand beach, practicing your swing on the golf course, or pampering yourself at the full-service spa. Then enjoy a meal at one of the resort's 3 restaurants.
Cheeca Lodge & Spa offers 243 accommodations with safes and coffee/tea makers. Rooms open to balconies. Beds feature premium bedding. 47-inch LED televisions come with premium cable channels.

Bathrooms include bathrobes, slippers, designer toiletries, and complimentary toiletries. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Additionally, rooms include hair dryers and irons/ironing boards. In-room massages and hypo-allergenic bedding can be requested. A nightly turndown service is provided and housekeeping is offered daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Excellent resort" - "The best property in the Keys. We loved it!" - "Probably the 2nd best resort I have stayed at in the Keys. Highly recommend! Lots of things to do in the resort such as pool, kayaking, paddle boarding, and bars. We also went fishing under the bridge near by and caught some nice fish! You can rent a boat at the resort but we didn’t as it wasn’t necessary since most boats came to the bridge to fish also. Had a great time and everyone in the area was very kind. "

A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations equipped with microwaves and refrigerators and easy access to attractions and activities. Relax and enjoy beautiful views from fully furnished private porches or lanais. Spend the afternoon lounging by the Islander's 2 on-site swimming pools. Enjoy on-site dining at Beachside Bar and Grill. Easily discover a variety of activities only minutes from the Islander Resort, including snorkeling and scuba diving. Enjoy deep-sea fishing, sailing or browsing the local shops, also only a short distance away.

- "We enjoyed our stay room was beautiful clean and wonderful staff. We enjoyed all the amenities that were offered! We" - "Private, secluded, uncrowded, and dog-friendly!" - "Stay longer" - "The location was perfect and close to restaurants in the area. Hope to return !" - "Will definitely return!" - "A relaxing stay with polite and attentive staff. The location is perfect for restaurants and attractions within walking" - "Relaxing time at a beautiful smallish resort on the beach!"

On private beach with outdoor pool, near Bud n' Mary's Dive Center
At Amara Cay Resort, spend the day on the private sand beach where you can enjoy snorkeling. Then return for a meal at one of the resort's 2 restaurants.
Change of towels is available on request.
Amara Cay Resort offers 110 air-conditioned accommodations with safes and coffee/tea makers. Each accommodation is individually furnished and decorated. Pillowtop beds feature Egyptian cotton sheets, down comforters, and premium bedding. Flat-screen televisions are featured in guestrooms.

Bathrooms include bathtubs or showers, bathrobes, complimentary toiletries, and hair dryers. Business-friendly amenities include desks and desk chairs, as well as phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Hypo-allergenic bedding and change of towels can be requested. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "The resort itself is amazing, just one thing that they need to work on is with the restaurant menu specifically breakfast " - "I would recommend this hotel the staff is super friendly. The hotel is clean. Q at the front desk made our stay at the hotel extra special. She was outstanding. I would definitely stay here again. " - "We had a great stay. The resort is so relaxing from the ocean swim to the pool. The resort staff was super friendly and I am already planning with my friends a time we can get back to enjoy for more!"

This beachfront hotel is located in Islamorada, Florida and features transfer services within 3.7 mi from the property. WiFi is included in the resort fee. Guests can relax on beachside hammocks or enjoy the outdoor pool at Amara Cay Resort. An on-site fitness center is available, as well as a meeting space. A flat-screen TV, work desk, and safety deposit box comes standard in every guestroom. Bicycle rentals and luggage storage are offered on site. Sample a custom cocktail at the Tiki Bar or experience Amara Cay Resort’s restaurant, ReelCatch. The History of Diving Museum is 3 mi away. Guests will be 8 minutes’ drive from Anne’s beach. Windley Key Fossil Reef Geological State park is 8 minutes’ drive.

- "Good price, beautiful grounds" - "Stunning stunning" - "Excellent" - "We had such a beautiful family vacation at Amara Cay we will definitely be returning." - "The best place for relax and romantic" - "Lovely staycation in Islamorada!" - "Had a great stay. Thank you" - "Amazing" - "Beautiful place and location. Great pool and pool bar!" - "Relaxing and exactly what we needed" - "The resort was great. Room service disappointed as they wouldn't report left items."

Beachfront, with outdoor pool
At La Siesta Resort & Villas, hit the private sand beach, relax by an outdoor pool, or spend the day at a marina.
Housekeeping is available on request.
La Siesta Resort & Villas offers 55 air-conditioned accommodations, which are accessible via exterior corridors and feature safes and coffee/tea makers. Each accommodation is individually decorated. Pillowtop beds feature Egyptian cotton sheets and premium bedding. Accommodations at this 4-star resort have kitchenettes with refrigerators and microwaves. Bathrooms include shower/tub combinations, designer toiletries, complimentary toiletries, and hair dryers.

Premium cable television is provided. Business-friendly amenities include desks, desk chairs, and phones. Additionally, rooms include irons/ironing boards and ceiling fans. Hypo-allergenic bedding and change of towels can be requested. Housekeeping is provided on request.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Good " - "We had a double room (upstairs and downstairs) rented on the south side of property which was very nice. Big spaces, big balcony with some view of the water. I didn’t pay attention enough but assume there would be a place to swim on beach there. There isn’t. Everything is close to do anything you want to do though and had a great time. The only complaint that I had is that there is no dishes in the kitchenettes." - "Overall the Property is very nice. COVID makes some things of course difficult ....like meeting new friends. Very Clean. The continental breakfast could have been handled a bit better more hospitality."

Just off the Overseas Highway and in front of the ocean, this Islamorada hotel offers an on-site marina. The beachfront hotel features an outdoor pool. WiFi is included in the resort fee. The suites and cottages at La Siesta Resort & Villas are equipped with a cable TV and air conditioning. On site, SIDECAR bar serves light fares, beer, and wine daily. Activities such as boating, fishing, jet skiing and snorkeling can be arranged. The on-site marina offers both gulf-side and ocean-side slips while non-motorized watersports equipment and bicycles are provided for guests' use. Theater of the Sea is 3.7 mi away from the accommodations while Anne's Beach is located 6.7 mi away.

- "A piece of paradise." - "Would not have wanted to stay anywhere but at La Siesta!" - "Wish we could have stayed, hope to go again." - "Absolutely Perfect" - "Tropical vacation in the US, we loved it!" - "A great location with exceptional rooms that exceeded my expectations" - "We had a wonderful stay in a beautiful comfortable clean cabana." - "I’m very happy with the Resort" - "Great location with amazing ocean views."

Family-friendly beachfront location with 3 outdoor pools
Spend the day relaxing on Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort's private sand beach or at a marina before returning for a meal at one of the resort's 4 restaurants.
Housekeeping is available on request.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort offers 214 accommodations, which are accessible via exterior corridors and feature safes and complimentary bottled water. Each accommodation is individually furnished and decorated. Refrigerators and coffee/tea makers are provided. Bathrooms include bathtubs or showers, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. 37-inch flat-screen televisions come with cable channels. Housekeeping is provided on request.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "We stayed for two nights in February. Great property and Italian restaurant" - "On its way back better then ever from before. Staff was amazing and so was the food and drink. Top notch" - "Awesome place, beautiful , lots to do , wish i could move there" - "It was a nice resort feel unlike any I have had in the keys" - "The entire staff was very friendly " - "Excellent and amazing property. I love this resort. Will be back"

Located on the waters of the Florida Bay, the Islander Bayside Resort is less than 5 minutes’ walk from the beach. This resort features a kitchen in every townhouse and an outdoor pool. A flat-screen TV is included in every guest townhouse of this Islamorada resort and all units have free WiFi and laundry facilities. Kitchens offer a microwave, refrigerator and an oven. Bicycle rental is possible on site and various water sport activities are located nearby. There are various dining options less than 1 mi from this resort and Windley Key Fossil Reef Park is 5 minutes’ drive away. Long Key is 15 minutes’ drive from the property. This hotel provides laundry valet service only.

- "Shuttle to other resort was great" - "Excellent Value, would definitely revisit" - "Will stay again...great for families dn walking distance to some great spots." - "Amazing place" - "Amazing Stay in a beautiful, clean and friendly place!" - "Beautiful place, very cosy" - "Quick, nice stay!" - "Brand new villa on a serene peaceful location with beautiful view over the gulf- great for watching sunsets!" - "Saved by Alice"

Beachside resort with outdoor pool
Guests at this beach resort will appreciate convenient onsite amenities such as charcoal grills and a picnic area.
Housekeeping is available on request.
Matecumbe Resort offers 36 accommodations with hair dryers and blackout drapes/curtains. Rooms open to patios. Accommodations offer separate sitting areas. Kitchens offer full-sized refrigerators/freezers, stovetops, microwaves, and separate dining areas. Bathrooms include showers.

Guests can surf the web using the complimentary wireless Internet access (speed: 100+ Mbps (good for 1–2 people or up to 6 devices)). Televisions come with cable channels. Irons/ironing boards, change of towels, and change of bedsheets can be requested. Housekeeping is provided on request.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "This hotel was the final stop on our Florida road trip, and it was exactly what my son and I needed—a place to unwind and relax. There were plenty of activities to enjoy, such as ping pong and kayaking, and the pool was well-maintained. We stayed in an apartment-style room in the building near the beach, and the sunrise views were spectacular. The only downside was the reception hours, which seemed to operate on "island time." While there are no nearby cafes or stores, the famous Robbie's of Islamorada is not too far away. If I visit the Florida Keys again, I wouldn't hesitate to stay here."

Offering a spa and wellness center and a garden, Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views! in Islamorada is close to Upper Matecumbe Key and History of Diving Museum. This vacation home provides air-conditioned accommodations with a balcony. The vacation home features parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. Theater of the Sea on Islamorada is 2.1 miles from the vacation home, while Windley Key is 2.7 miles from the property. Miami International Airport is 74 miles away.

Guest Services • Security/Safety • Wellness Facilities • Air Conditioner • Internet • Sports/Activities • Pool • Other • Parking • Spa • View • Breakfast

Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.

This listing is for a room within a hotel.

✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

———————————————

Guest Access:
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 04:00 pm.

✦ Pool available all year.
Additional features:
• Heated pool

———————————————

Other Things to Note:
There are several additional things to note:

✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.

✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

✦ We use multi-unit listings, so rooms are similar but may have small differences.

✦ There is a 7am-11pm front desk in the building that has the guest's information and keys ready. After these working hours you would be advised to our other sister resorts near by for check in.

Tv • Other • Fireplace/Heating • Air Conditioner • Security/Safety • Internet • Balcony/Terrace • Kitchen • Parking • Pool • Bedding/Linens • Laundry

Just a 12-minute walk from Upper Matecumbe Key and 0.7 miles from History of Diving Museum, Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location features accommodations in Islamorada with a garden. This villa offers air-conditioned accommodations with a balcony. The villa features parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom villa provides a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. Theater of the Sea on Islamorada is 2.1 miles from the villa, while Windley Key is 2.7 miles away. Miami International Airport is 74 miles from the property.

Other • Sports/Activities • Security/Safety • Parking • Air Conditioner • Pool • Wellness Facilities • Accessibility • Internet • Guest Services • Breakfast • View

Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. Hurricane Monument & Indian Key Historic State Park are a few miles away.

Our furnished 1BR Suite with Pool View, inspired by Islamorada's tropical beauty, offers comfort bedding and ample space to enjoy the tranquil ambiance. The place features natural decor and a range of amenities from a kitchenette to a balcony. Guests can enjoy on-site facilities including a restaurant, bar, swimming pool, and boat slips. For offsite adventures, a convenient shuttle service is available.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.

- The property requires a damage deposit of $100/day/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

- A mandatory resort fee of $55.13/night/room will be collected upon arrival. Please note that the resort fee is not included in the daily rate.

- Early check-in is subject to availability upon arrival.

- Please note that at least one guest in your party must be 21 years of age or older.

We're delighted you're considering RoomPick’s curated selection of boutique hotels, condo hotels, and resorts worldwide. This room comes with:

THE UNITS

Each 558sf One Bedroom Suite Pool View Two Queen features:
- 2 Queen beds;
- Pool View;
- Living Area;
- Sofa bed;
- Kitchenette;
- Coffee maker, Mini fridge, microwave;
- Dining table;
- All linens, towels, and bathroom essentials are provided. You don’t need to bring a thing!!

THE PROPERTY

Our family-friendly property provides the following on-site amenities:

- 24/7 Front desk and Security;
- Beachfront;
- Swimming pool;
- Loungers, umbrellas, and towels by the pool;
- On-site restaurant and bar;
- Shuttle service;
- Complimentary bikes, kayaks, and paddleboards;
- Boat slips (for rent);

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are allowed for an extra charge of USD 50 per pet, per day;

Air Conditioner • Guest Services • Fireplace/Heating • Internet • Pool • Bedding/Linens • Tv • Kitchen • Balcony/Terrace • Other • Parking • Wellness Facilities

Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.1 miles from Theater of the Sea on Islamorada. This villa features air-conditioned accommodations with a balcony. The villa offers parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom villa provides a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available at the villa, while guests can also relax in the garden. Windley Key is 2.7 miles from Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable, while Pigeon Key is 13 miles away. Miami International Airport is 74 miles from the property.

Guest Services • Security/Safety • Air Conditioner • Other • Pool • Wellness Facilities • Internet • Breakfast • View • Child Friendly • Parking • Sports/Activities

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.

✦ Each room is 540 sq. ft, equipped with complimentary toiletries, TV.

✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

———————————————

Guest Access:
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 04:00 pm.

✦ Pool available all year.
Additional features:
• Heated pool

———————————————

Other Things to Note:
There are several additional things to note:

✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.

✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

✦ We use multi-unit listings, so rooms are similar but may have small differences.

✦ There is a 7am-11pm front desk in the building that has the guest's information and keys ready. After these working hours you would be advised to our other sister resorts near by for check in.

Kitchen • Pool • Other • Security/Safety • Bedding/Linens • Internet • Air Conditioner • Laundry • Balcony/Terrace • Fireplace/Heating • Tv • Parking

Just a 12-minute walk from Upper Matecumbe Key and 0.7 miles from History of Diving Museum, Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location features accommodations in Islamorada with a spa and wellness center. This villa provides air-conditioned accommodations with a balcony. The villa offers parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom villa features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available at the villa, while guests can also relax in the garden. Theater of the Sea on Islamorada is 2.1 miles from Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location, while Windley Key is 2.7 miles from the property. Miami International Airport is 74 miles away.

View • Spa • Security/Safety • Pool • Sports/Activities • Other • Wellness Facilities • Air Conditioner • Breakfast • Internet • Parking • Guest Services

This listing is for a room within a hotel.

✦ Your room is 850 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

———————————————

Guest Access:
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 04:00 pm.

✦ Pool is available.

———————————————

Other Things to Note:
There are several additional things to note:

✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.

✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

✦ We use multi-unit listings, so rooms are similar but may have small differences.

Internet • Wellness Facilities • Guest Services • Balcony/Terrace • Fireplace/Heating • Air Conditioner • Bedding/Linens • Tv • Laundry • Parking • Pool • Security/Safety

Just a 12-minute walk from Upper Matecumbe Key and 0.7 miles from History of Diving Museum, Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location features accommodations in Islamorada with a spa and wellness center. This villa features air-conditioned accommodations with a balcony. The villa provides parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom villa offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available at the villa, while guests can also relax in the garden. Theater of the Sea on Islamorada is 2.1 miles from Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location, while Windley Key is 2.7 miles away. Miami International Airport is 74 miles from the property.

Other • Child Friendly • Wellness Facilities • Pet Friendly • View • Parking • Internet • Guest Services • Security/Safety • Spa • Sports/Activities • Breakfast

Two bedroom "gem" in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, relax in our hot tub or explore in our kayaks. Private boat ramp and boat slip!!

- "My husband and I enjoyed the property and amenities very much! Sunsets are amazing, there are bikes and kayaks to use and the villa itself was great. We needed some plumbing fixes and it was handled quickly. Everyone we dealt with was friendly." - "The property was great! A few steps to the beach. It was very relaxing and easily and comfortably fit our family of six." - "Great stay. The raised octagon cottages are very accommodating, comfortable, and clean. The resort offers a heated pool and hot tub, as well as a private sandy beach great for swimming, fishing, and watching sunsets. I docked a star for the online listing only because the pictures led me to believe the cottage was on the beach, when it was actually the furthest from it. This however wasn’t an issue at all, it was closest to the pool and a very short walk down there. Highly recommend."

Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.1 miles from Theater of the Sea on Islamorada. This vacation home provides air-conditioned accommodations with a balcony. The vacation home offers parking on-site, a spa center, and a 24-hour front desk. With free Wifi, this 3-bedroom vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available for guests at the vacation home. Windley Key is 2.7 miles from Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location, while Pigeon Key is 13 miles from the property. Miami International Airport is 74 miles away.

Parking • Sports/Activities • Other • View • Breakfast • Air Conditioner • Internet • Spa • Guest Services • Security/Safety • Wellness Facilities • Child Friendly

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

The Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home.

About The Caribbean Resort

Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "Pictures don’t do it justice. Place is amazing. Grounds are well cared for and everyone is so friendly. Complimentary bikes, kayaks, and fishing rods were great. Only negative was a little hassle in dealing with the booking agency but other than that it was so worth it." - "The Caribbean Resortoffered a gorgeous back drop for my recent family vacation. The friendliness of the staff and coziness of the unit completed this wonderful experience."

Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.1 miles from Theater of the Sea on Islamorada. This vacation home provides air-conditioned accommodations with a balcony. The vacation home features parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available at the vacation home, while guests can also relax in the garden. Windley Key is 2.7 miles from Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable, while Pigeon Key is 13 miles from the property. Miami International Airport is 74 miles away.

Internet • Air Conditioner • Parking • Other • Guest Services • Pool • Breakfast • Security/Safety • Child Friendly • View • Wellness Facilities • Sports/Activities

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

The Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "Enjoyed our stay in Islamodora, the property management team was awesome and responsive. The pool area is serene and loved hanging out there and on the massive front porch. Perfect place for quiet time and relaxation. Only suggestions is to stock salt and pepper - otherwise kitchen is very well equipped." - "I was nervous renting this house as there were no reviews at the time. I reached out to ask why no reviews and it was a new property/rental. I am so pleased to have booked and stayed there. The office staff were super friendly and helpful. The house was beautiful and had the best covered porch. You can use the kayaks, bikes and paddle boards which was a bonus. The bed was one of the most comfortable beds I have slept in...You can walk to restaurants, it's a great location. We will 100% stay here again..."

Facing the beachfront, Breezy Palms Resort offers 3-star accommodations in Islamorada and has an outdoor swimming pool, private beach area and terrace. The property is located 2 miles from Upper Matecumbe Key, 4.5 miles from Theater of the Sea on Islamorada and 5.1 miles from Windley Key. Free WiFi is available and private parking can be arranged at an extra charge. Complete with a private bathroom equipped with a shower and free toiletries, the rooms at the hotel have a flat-screen TV and air conditioning, and certain rooms come with a balcony. Guest rooms will provide guests with a fridge. Speaking both English and Spanish, staff at the reception can help you plan your stay. Pigeon Key is 15 miles from Breezy Palms Resort, while John Pennekamp State Park is 23 miles from the property. Miami International Airport is 76 miles away.

- "Heaven on the beach!" - "We enjoyed our night there. Very quiet, nice lounge chairs, outside bathroom was great. Most don’t have that. I’d stay t" - "I am coming back I found a new vacation spot!!" - "Great find!" - "Wonderful" - "Had a really nice time!" - "Only stayed one night but a great base for exploring the Keys" - "Good place for a stopover." - "Fab establishment on the water!" - "Exactly what you pay for. Very clean"

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "Great amenities, great view, great housekeeping staff."

Located right on the shores of Islamorada, the Fisher Inn Resort & Marina is 14 miles from Key Largo. Guests will enjoy convenient beach access and a boat ramp as well as an outdoor pool and outdoor games on the property. Free Wi-Fi is included in all rooms of this Islamorada hotel and guests can also enjoy cable TV in the rooms. Some units offer a kitchenette so guests can prepare their own meals during their stay. Laundry facilities is available on site at the Fisher Inn Resort & Marina. Guests will also be able to enjoy various activities such as fishing, windsurfing, kayaking, paddle boarding and snorkeling during their stay. This oceanfront hotel is less than 10 minutes’ walk from the Theater of the Sea. The Holiday Isle Marina is also less than 1 mile away.

- "Great quite Hotel" - "This was a great place for my weekend stay." - "Loved it here" - "Had a great time. Grand daughter enjoyed the pool and all of the games" - "Will go back for sure!!" - "Comfortable, clean and convenient location with great ocean view." - "Good but the pet fee should be $25 per day instead of $50 considering housekeeping only made the beds, supplied fresh to" - "We love the fisher inn and will continue to stay there!"

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "I plan all of our family trips. Decades of them. Only detail I give is sand or snow. Always concerned about MY reviews! The Caribbean Resort delivered in each & every way!! Fam says: Great Job, Loved It, Keep It Up. YAY! Loved It- strongly recommend" - "Absolutely phenomenal experience! Very nice staff. Truly a home away from home with subzero, Viking appliances, blackout window shutters & air conditioning!. Great location! Private gate! we will definitely be returning! Thank you everyone *** the only thing I would love to see upgraded Next time we come is the mattresses. The beds were awful for me, but I’m used to Tempur-pedic and weigh 230 💪"

Guests at this Islamorada oceanfront resort can enjoy free WiFi access. Windley Key Fossil Reef Geological State Park is 2 miles away. A 37-inch flat-screen cable TV and a small refrigerator are offered in each room at this Florida Chesapeake Beach Resort. Select rooms and suites have a balcony. Chesapeake Beach Resort features an outdoor pool with an ocean view. Guests can check out the History of Diving Museum (3 minutes’ walk) or see a show at the Theater of the Sea (4 minutes’ drive).

- "My husband and I took a vacation. The Chesapeake resort was so relaxing so beautiful so very clean in the hospitality wa" - "Love it" - "Bewutiful, tranquil, relaxing. Very clean and the staff was exceptional!" - "The staff was very helpful, pleasant and friendly."

Experience paradise like a local in this superb 2-bedroom 2 bath Villa with private patio and your own on premises boat slip and launch site. Master bedroom includes a king bed, the guest room has 2 twin beds, while the living room offers an additional queen sofa bed. Air conditioned, WiFi, washer/dryer, fully equipped kitchen + outdoor grill. All linens plus beach towels are included. Topsider Resort offers an exclusive private sand beach perfect for snorkeling, sunning and relaxing, Fish directly from the Topsider dock which is also the place to be for the evening sunset celebration. Other amenities include heated pool + Jacuzzi, tennis/pickle ball courts and complimentary kayaks and bicycles for your use. At mile maker 75.5, Topsider is perfectly located to enjoy the best of the Florida Keys,

- "We enjoyed our stay here, although units are older and do need some sprucing up.It was nice to have a beach onsite, as well as a heated pool, the use of (older) bikes and kayaks. We were only a few miles from the action of Islamorada, including restaurants, tourist attractions, shopping, breweries"

This Islamorada resort in the Florida Keys is located near Alligator Reef. It features an oceanfront freshwater pool, a Tiki Bar and a private beach area. Each accommodations includes a full kitchen. A living area with a cable TV is included in all units at Pines & Palms Resort. The traditionally styled units feature light colors and island decor. Most offer a private terrace with ocean views. Guests at Resort Palms & Pines have access to kayak and bike rentals, private boat docks and premium sport fishing areas. A covered cabana with a barbecue grill, fridge and sink is available for guest use. This resort is less than 1 mi from Miss Islamorada Fishing Charters. The entrance to John Pennekamp Coral Reef State Park is less than 30 minutes’ drive away.

- "Amazing stay!" - "Rest and relaxation" - "Amazing stay" - "Wish we could've stayed longer. We hope to get a chance to return." - "Home away from home" - "Palms & Pines - our home away from home - so glad we chose this place!" - "Family weekend" - "Strategic position!" - "Exceptional stay" - "Great place to stay in the keys." - "Relaxing getaway, you feel like your on a Caribbean island without leaving the states."

Welcome to The Bird of Paradise. This Oceanfront home has everything you need for a relaxing getaway. Custom High ceilings create an open, airy feel to this one bedroom, one bathroom home. The Bird of Paradise has a fully appointed kitchen with everything you need to cook up your fresh catch, or, use the Weber gas grill on your front patio. Just steps away from our marina and activity center, where you will find complimentary bikes, paddleboards, kayaks and fishing poles. Enjoy your morning coffee on the patio, in oversized chairs while watching the sun rise over our world-famous dock. The interior is impeccably decorated with fine furnishings from Tommy Bahama, accessories and wall art from Ocean Gardens, all with your comfort in mind. Cable television is located in the living room as well as the bedroom. Wifi and air conditioning are accessed throughout the home.

The Bird of Paradise is The Caribbean Resort's ADA accessible home. This home is held for use by individuals with disabilities until all other guest rooms have been rented.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "It was what we all want— just deliver as advertised." - "Good"

Located adjacent to Windley Key Fossil Reef Geological State Park, this Islamorada resort features an ocean-side outdoor swimming pool. Beach towels, Kayaks, Paddle-boards & WiFi are included at this oceanfront resort and marina. A microwave, refrigerator and coffee-making facilities come standard in each a room at Drop Anchor Resort & Marina Resort and Marina. A flat-screen TV is also included. Trailer parking and boat docking are possible at Drop Anchor Resort & Marina Resort. Barbecue facilities, outdoor dining areas and hammocks are available as well. Theater of the Sea is just 9 minutes’ walk from Drop Anchor Resort & Marina Resort and Marina. Guests will be 6.9 miles from Indian Key Historic Park.

- "Will definitely stay here again!" - "Perfect getaway" - "I want to shut out the receptionist, he’s so nice and so humble. I believe he’s really passionate about his job. I was s" - "Very comfortable" - "Nice view but cannot swim in the private beach" - "Great value for the location and amenities. Would definitely stay here again" - "I enjoyed Drop Anchor enough to revisit but disappointed with the additional charge, when I feel we already paid a fair"

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "This place is fantastic! The cottage was spectacular, clean, and more than what we expected. The pictures don’t do it justice. It was even better in person. The tropical pool area was even better than the cottage! If you are considering staying here, don’t pass it up. It’s a winner!" - "Property great your services way too high. Will never use your services again"

Offering an outdoor pool and sun terrace, Caloosa Cove Resort is located in Islamorada in the Florida Region, 6 mi from Upper Matecumbe Key. Theater of the Sea on Islamorada is 11 mi from the property. All units feature a flat-screen TV, a balcony, and fully equipped kitchen. Some units have 2 flat-screen TVs and 2 balconies with an ocean view. Unites also have 1 or 2 full bathrooms. Towels are exchangeable daily. Even though this is a beachfront resort not every room has a water view. Guests can enjoy a meal at the on-site restaurant. The property has a private beach area. The area is popular for fishing. Windley Key is 11 mi from Caloosa Cove Resort, while Windley Key Fossil Reef Geological State Park is 11 mi away.

- "We’d stay again." - "It was a perfect spot! Beautiful, quiet, easy." - "Perfect, quiet getaway" - "So relaxing and fun! Staff super nice." - "Great place to stay would stay again." - "Beautiful, relaxing location." - "Next to the Sea Base for Scouts!" - "Great resort and I am already planning on next year to stay there" - "We had a wonderful stay and would definitely come back." - "A peaceful retreat in a picturesque setting."

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "Beautiful location. Fantastic House every detail. Pool Grounds were perfection. Waterfront was perfect. Staffing were on point."

Featuring a unique tropical atmosphere and located on an island in the Florida Keys, this resort offers WiFi and parking to guests. A cable TV and a private bathroom are included in every guestroom. A in-room safes is also provided. Guests of Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort can stop by the marina to charter a fishing trip or rent a jet ski. Guests seeking adventure will enjoy snorkeling and diving charter boats. Windley Key Fossil Reef Geological Park is just 3 minutes’ drive from the property while Key Largo is 21 minutes’ drive.

- "Was impressed 10 stars" - "Amazing.highly recommend" - "Magnificent views - great staff - will be back!" - "Last minute booking saved the weekend!" - "WONDERFUL RESORT / STAY / SERVICE!!!" - "Beautiful birthday stay with my husband." - "Amazing" - "Had a wonderful time" - "We had a nice 5 days there" - "We will return!" - "Nice clean resort friendly staff, good location." - "A little bit or paradise"

Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.

This listing is for a room within a hotel.

✦ Your room is 540 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

———————————————

Guest Access:
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 04:00 pm.

✦ Pool available all year.
Additional features:
• Heated pool

———————————————

Other Things to Note:
There are several additional things to note:

✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.

✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

✦ We use multi-unit listings, so rooms are similar but may have small differences.

✦ There is a 7am-11pm front desk in the building that has the guest's information and keys ready. After these working hours you would be advised to our other sister resorts near by for check in.

- "Very good stay. Furniture was dirty and tv cable didn’t always work. But good overall "

Featuring free WiFi and an outdoor pool, La Jolla Resort offers accommodations in Islamorada, 2625 feet from Upper Matecumbe Key. Free private parking is available on site. All rooms include a flat-screen TV. Every room comes with a private bathroom fitted with a shower. Extras include free toiletries and a hair dryer. There is a shared lounge at the property. This inn has a private beach area. You can engage in various activities, such as cycling and fishing. Theater of the Sea on Islamorada is 2.3 mi from La Jolla Resort, while Windley Key is 2.7 mi from the property. Anne's Beach is 11 minutes' drive.

- "Nice place. The Kids loved it." - "What a perfectly simple" - "Cool retro vibe. We loved it" - "We love Islamorada. La Jolla is a perfect little stop while in the Keys." - "Awesome!" - "Lovely property" - "Decent stay" - "Great Islamorada location, staff, comfy room."

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

About The Caribbean Resort

Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "Spacious and beautiful place with tropical pool a few steps away. Enjoyed our stay immensely."

Matecumbe Resort features a public bath and air-conditioned accommodations in Islamorada, 1.2 miles from Sea Oats Beach. This beachfront property offers access to table tennis, free private parking, and free Wifi. This 2-star condo hotel offers private entrance. The condo hotel provides guests with a balcony, garden views, a seating area, cable flat-screen TV, a fully equipped kitchen with an oven and a microwave, and a private bathroom with shower and a hair dryer. A toaster, a fridge, and stovetop are also available, as well as a coffee machine. At the condo hotel, every unit is fitted with bed linen and towels. For those times when you'd rather not eat out, you can cook on the barbecue. The area is popular for cycling, and free use of bicycles is available at Matecumbe Resort. The accommodation has both a sun terrace and garden where you can relax, along with a private beach area. Upper Matecumbe Key is 5.7 miles from Matecumbe Resort, while Theater of the Sea on Islamorada is 8.2 miles from the property. Key West International Airport is 73 miles away.

- "This place is a gem 💎" - "Excellent" - "Great" - "This was described as an economy resort. It was beyond our expectations. Lovely location." - "If we would have the chance, we would definetely be back" - "Short getaway to decompress, this filled my needs!" - "Despite the heavy storm and the air conditioning noise it was worth knowing that beautiful place." - "Matecumbe vacay" - "Didn‘t like the appartment. Dark living room and bad smell."

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in”(Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

- "Bea"

Located in Islamorada, a 9-minute walk from Windley Key, Coconut Cove Resort & Marina provides accommodations with an outdoor swimming pool, free private parking, a fitness center and a shared lounge. This 2-star inn offers a business center, a concierge service and free WiFi. Certain units at the property include a balcony with a sea view. Selected rooms include a kitchen with a fridge, an oven and a microwave. Guests at the inn can enjoy a buffet or a continental breakfast. Coconut Cove Resort & Marina has a terrace. Guests at the accommodation will be able to enjoy activities in and around Islamorada, like fishing and cycling. Theater of the Sea on Islamorada is a 7-minute walk from Coconut Cove Resort & Marina, while Upper Matecumbe Key is 3 miles away. Miami International Airport is 72 miles from the property.

- "Just great stay, definitely come back !" - "We will be back when we can stay longer!" - "We loved it!" - "Best getaway" - "Good value for money. Would definitely recommend this place" - "Amazing." - "Worth the money I paid" - "Adequate with clean sheets in a tiny room with very old furniture. There was a makeshift king headboard on a queen bed a" - "Enjoyed the view and beach/pool area. Room was a little outdated in older building with a few upgra"

Escape to paradise in this gorgeous 3-bedroom, 3-bathroom townhome is located at Executive Bay Club in Islamorada, FL. Ideal for family getaways or group vacations, this townhome offers two luxurious king beds and a trundle bed in the loft, ensuring ample space for everyone.

Enjoy breathtaking ocean views and take full advantage of the incredible amenities at Executive Bay Club! Located right next to Founder's Park, this townhome offers endless options for recreation and relaxation.

Balcony/Terrace • Internet • Wellness Facilities • Pool • Kitchen • Parking • Sports/Activities • View • Child Friendly • Bedding/Linens • Tv • Ocean View

Located in Islamorada, 1.9 miles from Windley Key, Ragged Edge Resort & Marina has accommodations with free bikes, private parking, an outdoor swimming pool and a terrace. Located around 5.2 miles from Upper Matecumbe Key, the resort with free WiFi is also 8.7 miles away from Pigeon Key. Some accommodations at the property have a balcony with a sea view. Selected rooms also feature a kitchen with a fridge, an oven and a microwave. The resort has a grill. Guests at Ragged Edge Resort & Marina will be able to enjoy activities in and around Islamorada, like fishing and cycling. John Pennekamp State Park is 17 miles from the accommodation, while Windley Key Fossil Reef Geological State Park is 2.7 miles from the property. The nearest airport is Miami International Airport, 70 miles from Ragged Edge Resort & Marina.

- "AMAZINGLY refreshing and chillax as my 18 yr old daughter would say!" - "Relaxing,beautiful suites, warm welcoming, exceptional customer service." - "Paradise" - "Great deal in comparison to an airbnb" - "-perfect for our needs" - "This is a hidden gem of a site....will be returning next year"

Experience Islamorada like a local in this superb 1-bedroom resort. The cozy bedroom features a king bed for a restful night's sleep. Relax in the lovely living room with a comfy sofa bed for additional guests. This fabulous property also offers amenities like WiFi and AC for your convenience. Fall in love with Islamorada and enjoy the magic it has to offer.

Child Friendly • Internet • Security/Safety • Air Conditioner • Other • Bedding/Linens • Laundry • Wellness Facilities

Topsider Resort features free bikes, outdoor swimming pool, a garden and private beach area in Lower Matecumbe Beach. Featuring family rooms, this property also provides guests with a grill. Guests can use the hot tub, or enjoy pool views. The hotel will provide guests with air-conditioned rooms offering a closet, a coffee machine, a fridge, a dishwasher, a safety deposit box, a flat-screen TV, a terrace and a private bathroom with a shower. Free WiFi is available to all guests, while some rooms come with a balcony. All guest rooms will provide guests with an oven. Activities such as fishing, snorkeling, canoeing can be enjoyed in the surrounding areas, and guests can relax along the beachfront. Sea Oats Beach is a 7-minute walk from Topsider Resort, while Upper Matecumbe Key is 6.5 miles away. Key West International Airport is 73 miles from the property.

- "A perfect location" - "Lovely !" - "Love peaceful beach location with everything you need!" - "wonderful relaxing time" - "Nice place but rooms need to be rehabbed."

This home has an upscale decor package and is fully furnished - just bring your suitcase.

While here, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. Including, a heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.

Islamorada is the fishing capitol of the world, and you will easily find plenty of nice dining locally. Founders park is directly across the street for those that wish to walk over and have a day at the beach, or just play some pickle ball.
A min of 28 nights is required for these homes.

Child Friendly • Bedding/Linens • Fireplace/Heating • Internet • Wellness Facilities • Air Conditioner • Laundry • Security/Safety

Ocean Waves Below Your Balcony – Your Private Escape in the Florida Keys

Welcome to a one-of-a-kind oceanfront home where the Atlantic Ocean surrounds you on two sides, creating a constant symphony of rolling waves and salty breezes. This is not just another vacation rental—this is your front-row seat to island paradise, where every sunrise is a masterpiece and every evening brings peace.

Minimum stay: 28 nights – perfect for extended vacations, seasonal retreats, work-from-paradise escapes, or those dreaming of sampling the Isla Life before making it permanent.

BREATHTAKING OCEANFRONT SETTING

This home is positioned in one of the most desirable oceanfront locations in Islamorada. The water is so close, you can hear the waves gently lapping the shoreline from nearly every room in the house.

*Direct Atlantic Ocean exposure on two sides
*Spectacular sunrise views
*Enjoy coffee or cocktails from your private balcony just off the main floor
*Feel completely immersed in the natural beauty of the Florida Keys

ABOUT THE HOME – Windjammer Floorplan (2 Bedrooms Upstairs)

This thoughtfully designed pet-friendly coastal retreat spans 1,230 sq. ft. and is ideal for travelers seeking both comfort and serenity.

Main Floor Features:

*Fully equipped gourmet kitchen with stainless steel appliances, quartz countertops, farm sink, custom cabinets, and full dining area
*Open-concept living room with panoramic ocean views
*Private ocean-view balcony off the main living area – perfect for relaxing outdoors, dining al fresco, or enjoying the ocean breeze
*Convenient full bathroom
*In-unit washer and dryer

Second Floor Features:

Two private bedrooms upstairs, both designed for comfort and privacy
Primary bedroom with ocean views and luxury bedding
Second bedroom perfect for guests or family members
Full upstairs bathroom with resort-style finishes

This Windjammer model does not include a loft. All sleeping accommodations are located upstairs to create a peaceful, restful environment separate from main floor entertaining.

Sleeps up to 6 comfortably with the addition of a sleeper sofa in the main living area.

FULLY FURNISHED WITH COASTAL STYLE

This home comes fully furnished in a tropical resort-inspired theme. Each home is privately owned and decorated, which means furnishings may vary slightly—but all units meet professional resort standards for comfort and quality. Everything you need is here, including:

*Linens & towels
*Cookware & dishes
*Kitchen essentials & small appliances
*Comfortable seating & bedding
*Decor designed to reflect the spirit of the Keys
*Just bring your suitcase, and the island life begins.

RESORT AMENITIES INCLUDED

As a guest in this oceanfront rental, you will enjoy full access to an exclusive waterfront resort offering the best of island living:

WATER & RELAXATION

Heated oceanfront swimming pool
Lounge chairs along the ocean’s edge
Oceanfront boardwalk for sunrise walks
Easy water access for paddleboarding and kayaking

ACTIVITIES & ENTERTAINMENT

Clubhouse with social spaces
Outdoor game lawn & billiards
Daily and weekly resort activity schedule
Live music (seasonal)
Community events, game nights, fitness gatherings

WELLNESS

*Fitness center
*Yoga and outdoor wellness activities (seasonal)
*Ocean air, peace, and rejuvenation at every turn

ISLAMORADA - THE ULTIMATE KEYS EXPERIENCE

Located in the heart of Islamorada, you are just minutes from:

Fine dining restaurants featuring fresh local seafood
World-class fishing charters (offshore, reef, and backcountry)
Founders Park – directly across the street with a beach, pickleball courts, dog park, marina, and walking trails
Marine life encounters, snorkeling excursions, sunset cruises, and eco-tours
Art galleries, boutiques, and the Morada Way Arts District
Florida Keys Brewing Co museums, historical landmarks, and more

Islamorada is truly a playground for outdoor lovers, foodies, and anyone seeking tranquility in a stunning tropical environment.

WHY GUESTS LOVE THIS HOME

*Unmatched oceanfront setting
*Balcony directly off the main floor
*Two bedrooms upstairs for privacy and comfort
*Fully furnished, turn-key living
*Full kitchen for cooking meals at home
*Resort amenities included
*Peaceful, private, and secure resort setting
*Perfect for month-long stays

MINIMUM STAY REQUIREMENT

To preserve the peaceful residential experience and comply with community guidelines, a 28-night minimum stay is required.

This makes the property ideal for:

*Extended vacations
*Monthly corporate stays
*Seasonal/winter escapes
*Relocation visits
*Long-term island lifestyle experiences

BOOK YOUR STAY - LIVE THE ISLAND LIFE

Whether you choose to spend your days relaxing by the pool, fishing offshore, exploring coral reefs, or lounging on your balcony listening to the ocean, this Windjammer home offers the perfect setting to recharge your soul.

Homes like this are rare, and availability is limited.
Secure your dates now and start living the vacation lifestyle you’ve always dreamed of.

The Isla Life starts now – and it starts here.

Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

Tv • Other • Parking • Security/Safety • Internet • Laundry • Air Conditioner • Fireplace/Heating • Pool • Kitchen • Bedding/Linens • Balcony/Terrace

This brand new home is sitting quietly behind a controlled access gate with a private balcony overlooking the Atlantic Ocean. Full two bedroom, two bath floor plan, has an upscale decor package and is fully furnished - with an optional work-from-vacation home set up in bedroom 2.
While your experience will be private, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. Including, but not limited to, heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.
Islamorada is the fishing capitol of the world, and you will easily find plenty of nice dining locally. Founders park is directly across the street for those that wish to walk over and have a day at the beach, or just play some pickle ball.

Check out the video of our home below:
https://youtu.be/vs-ChBQAxzc

Child Friendly • Balcony/Terrace • Bedding/Linens • Pool • Internet • Laundry • Security/Safety • Wellness Facilities • Air Conditioner • Fireplace/Heating

This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full two bedroom, two bath floor plan, has an upscale decor package and is fully furnished - just bring your suitcase.

While your experience will be private, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. Including, but not limited to, heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.

Islamorada is the fishing capitol of the world, and you will easily find plenty of nice dining locally. Founders park is directly across the street for those that wish to walk over and have a day at the beach, or just play some pickle ball.

Fireplace/Heating • Pool • Hot Tub • Security/Safety • Laundry • Internet • Other • Kitchen • Air Conditioner • Spa • Wellness Facilities • Parking

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in (Our office is open 8:30am to 4:30pm.)

Sleeps : Guest count is firm and cannot exceed the max capacity

Internet • Kitchen • Bedding/Linens • Balcony/Terrace • Security/Safety • Guest Services • Air Conditioner • Parking • Pool • Laundry • Private Pool • View

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

About The Caribbean Resort
Our Caribbean homes are named in honor of Hemingway, the beautiful Canary Island Jamaican Malayan Princess and Royal Palm trees that grace our resort. These homes rest on white-sand grounds among luxuriant tropical flower gardens and arching palms that sway in the gentle ocean breezes. Just steps away from the emerald-green oceans edge. Endless piers and a beach-entry pool awaits your arrival. Coconut palms arching gracefully over the pool. Fresh water lapping at your toes as you enter the beach. Our one-of-a-kind pool is a natural oasis that gives life to gardens of tropical flowers and pineapple palm and banana trees. Waterfalls cascade over heated rock into our spa and pool. Private sun decks are scattered throughout the grounds. Gazebos, tables, chairs and lounges are comfortably placed for your enjoyment.

All homes include daily housekeeping. Boat slip availability must be confirmed at time of booking. Dock Space is Limited and available on a first come first serve basis. Boat dockage is a separate fee due upon check in”(Our office is open 8:30am to 4:30pm.)

Sleeps : guest count is firm and cannot exceed the max capacity

Pool • Air Conditioner • Security/Safety • Laundry • Private Pool • Balcony/Terrace • Barbecue/Outdoor Cooking • Parking • Bedding/Linens • Tv • Internet • Kitchen

Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. Hurricane Monument & Indian Key Historic State Park are a few miles away.

The space
This listing is for a room within a hotel.

✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

Guest access
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 4:00PM.

✦ Pool is available.

Other things to note
There are several additional things to note:

✦ A valid credit or debit card is required for the refundable security deposit and any offline fees displayed upon completing your Airbnb reservation.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

✦ We use multi-unit listings, so rooms are similar but may have small differences.

Bed linens • TV • Extra pillows and blankets • Iron • Hangers • Shampoo • Dryer • Essentials • Air conditioning • Hair dryer

Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. Hurricane Monument & Indian Key Historic State Park are a few miles away.

The space
Our furnished 1BR Suite with Pool View, inspired by Islamorada's tropical beauty, offers comfort bedding and ample space to enjoy the tranquil ambiance. The place features natural decor and a range of amenities from a kitchenette to a balcony. Guests can enjoy on-site facilities including a restaurant, bar, swimming pool, and boat slips. For offsite adventures, a convenient shuttle service is available.

PLEASE NOTE:
This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.

- These are TWO separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.

- The property requires a damage deposit of $100/day/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

- Early check-in is subject to availability upon arrival.

- Please note that at least one guest in your party must be 21 years of age or older.

We're delighted you're considering RoomPick’s curated selection of boutique hotels, condo hotels, and resorts worldwide. This room comes with:

THE UNITS

Each 558sf One Bedroom Suite Pool View Two Queen features:
- 2 Queen beds;
- Pool View;
- Living Area;
- Sofa bed;
- Kitchenette;
- Coffee maker, Mini fridge, microwave;
- Dining table;
- All linens, towels, and bathroom essentials are provided. You don’t need to bring a thing!!

THE PROPERTY

Our family-friendly property provides the following on-site amenities:

- 24/7 Front desk and Security;
- Beachfront;
- Swimming pool;
- Loungers, umbrellas, and towels by the pool;
- On-site restaurant and bar;
- Shuttle service;
- Complimentary bikes, kayaks, and paddleboards;
- Boat slips (for rent);

PARKING
Parking is available for guests on the property and is free of cost (for 1 car per unit).

PET POLICY
Pets are allowed for an extra charge of USD 50 per pet, per day;

Guest access
There is a 24/7 front desk in the building that handles the keys. The guests can keep their luggage at the front desk before check-in and after check out.

Other things to note
We have more units to accommodate larger groups

TV • Essentials • Iron • Hangers • Bed linens • Hair dryer • Extra pillows and blankets • Shampoo • Dryer • Air conditioning

Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. Hurricane Monument & Indian Key Historic State Park are a few miles away.

The space
This listing is for a room within a hotel.

✦ Your room is 618 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

Guest access
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 4:00PM.

✦ Pool is available.

Other things to note
There are several additional things to note:

✦ A valid credit or debit card is required for the refundable security deposit and any offline fees displayed upon completing your Airbnb reservation.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

✦ We use multi-unit listings, so rooms are similar but may have small differences.

Iron • Bedroom and laundry • Hair dryer • Essentials • Dryer • Shampoo • Hangers • Bathroom • Extra pillows and blankets • Bed linens

Escape to laid-back island living at La Siesta Resort & Villas in Islamorada. Set on a private beachfront with tropical suites, enjoy poolside cocktails at Sidecar, kayak and paddleboard rentals, and shared access to sister resorts via water taxi or shuttle. Ideal for families, couples, or groups seeking a serene Keys getaway.

The space
This listing is for a room within a hotel.

✦ Your room is 717 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

Guest access
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 4:00PM.

✦ Pool available all year.
Additional features:
• Heated pool

Other things to note
There are several additional things to note:

✦ A valid credit or debit card is required for the refundable security deposit and any offline fees displayed upon completing your Airbnb reservation.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

✦ We use multi-unit listings, so rooms are similar but may have small differences.

✦ There is a 7am-11pm front desk in the building that has the guest's information and keys ready. After these working hours you would be advised to our other sister resorts near by for check in.

Hangers • Heating • TV • Air conditioning • Shampoo • Essentials • Bed linens • Iron • Extra pillows and blankets • Hair dryer

Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. Hurricane Monument & Indian Key Historic State Park are a few miles away.

The space
✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

Guest access
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 4:00PM.

✦ Pool is available.

Other things to note
There are several additional things to note:

✦ A valid credit or debit card is required for the refundable security deposit and any offline fees displayed upon completing your Airbnb reservation.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets

Essentials • Hair dryer • Hangers • Bed linens • Shampoo • TV • Heating • Extra pillows and blankets • Iron • Air conditioning

Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. Hurricane Monument & Indian Key Historic State Park are a few miles away.

The space
✦ Your room is 1350 sq. ft, equipped with complimentary toiletries, TV.

✦ Daily cleaning services included in the nightly price.

There are a few additional details to know before you book:

✦ The minimum age required for check-in is 21 years old.

✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.

Guest access
During your stay, you will have access to the property and amenities according to the following schedule:

✦ Check-in is available from 4:00PM.

✦ Pool is available.

During your stay
I give my guests space but am available when needed

Other things to note
There are several additional things to note:

✦ A valid credit or debit card is required for the refundable security deposit and any offline fees displayed upon completing your Airbnb reservation.

✦ Pets are welcome. $50 per pet per day, with a max of 2 pets