Premier Resorts in Islamorada

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.

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

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

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.

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

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;

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

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.

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

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.

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

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.

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

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.

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

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.

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

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."