Best Villa Rentals in Islamorada

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."

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a Smart TV, as well as Netflix and a coffee/tea maker. Other amenities include designer toiletries, premium bedding, a pillowtop bed, and towels.

- "We came the Labor Day weekend, to celebration two birthdays. It was a first for our family and we were pleasantly amazed by the property and all its amenities. We kayaked, sailed, played pickleball, biked and had a lot of fun overall. Our elderly mother was able to very comfortably relax inside, while enjoying the breathtaking views of the ocean from our balcony. We travel internationally several times a year,and this was one of our most relaxed vacations! But most noteworthy is the staff...they were all very attentive to our needs, super responsive and always with a smile. This was a top notch weekend, and we will absolutely be back. Special thanks to Mary at the front desk, who was the perfect host, very helpful with our elderly mother and so lovely! And Emanuel at the kayak stand who was always helpful and ready to assist."

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"

Set along a private beach in Islamorada, La Siesta Resort & Villas features studios 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.

✦ 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

✦ 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.

- "The staff is super friendly. We had a perfect stay!" - "We enjoyed our 4 day stay at this resort. The tropical vegetation is lush and provides privacy. The large room easily accommodated the 4 of us. It has a nice roomy balcony with chairs for relaxation. The large pool is very nice with plenty of shallow area for small children. And plenty of loungers for sunning and relaxation. The only drawback was the tiki bar did not have a liquor license so all drinks were either beer or wine based. Otherwise awesome place to stay."

Just a 5-minute walk from Windley Key and 0.7 miles from Theater of the Sea on Islamorada, Anglers Reef Vacation Rental features accommodations in Islamorada with barbecue facilities. This property offers access to a balcony and free private parking. The pool features a fence and garden views. With free Wifi, this 2-bedroom villa offers a cable flat-screen TV, a washing machine, and a fully equipped kitchen with kitchenware. The accommodation is non-smoking. Guests at the villa will be able to enjoy activities in and around Islamorada, like fishing and canoeing. Snorkeling and cycling can be enjoyed nearby, while a private beach area and water sports facilities are also available on-site. Upper Matecumbe Key is 3.4 miles from Anglers Reef Vacation Rental, while Pigeon Key is 10 miles from the property. Miami International Airport is 71 miles away.

Parking • Wellness Facilities • Air Conditioner • Pool • Security/Safety • Oceanfront • Sports/Activities • Barbecue/Outdoor Cooking • Private Beach • Balcony/Terrace • Guest Services • Ocean View

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 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 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.

- "It was wonderful! Perfect for a family with older kids due to have separate sleeping areas. The pool was very nice and clean! "

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.

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

Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, watersport 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 1065 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.

✦ 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.

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

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.

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

Relaxing and indulgent stay on the tropical islands of Islamorada!

✦ 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 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

Other • Internet • Ocean View • Oceanfront • Kitchen • Wellness Facilities • Fireplace/Heating • View • Bedding/Linens • Parking • Security/Safety • Laundry

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.

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

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.

✦ 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 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

Child Friendly

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.

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

Relaxing and indulgent stay on the tropical islands of Islamorada!

✦ 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 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

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

Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key. This villa offers air-conditioned accommodations with a balcony. The accommodation provides a 24-hour front desk and parking on-site. 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. Pigeon Key is 13 miles from Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable, while John Pennekamp State Park is 21 miles from the property. The nearest airport is Miami International Airport, 74 miles from the accommodation.

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

Set along a private beach in Islamorada, La Siesta Resort & Villas features studios 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.

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

1.6 miles from Sea Oats Beach in Islamorada, Villa Riolo provides accommodations with access to a spa center. Both free Wifi and parking on-site are available at the vacation home free of charge. Windley Key is 8.8 miles from the vacation home and Pigeon Key is 19 miles away. The vacation home is composed of 2 bedrooms, a fully equipped kitchen, and 2 bathrooms. The accommodation is non-smoking. A water park is also available for guests at Villa Riolo. Upper Matecumbe Key is 5.7 miles from the accommodation, while Theater of the Sea on Islamorada is 8.2 miles away. Key West International Airport is 74 miles from the property.

View • Internet • Accessibility • Oceanfront • Wellness Facilities • Other • Security/Safety • Fireplace/Heating • Sports/Activities • Air Conditioner • Parking • Guest Services

Relaxing and indulgent stay on the tropical islands of Islamorada!

✦ 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 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

Pool • Tv • Air Conditioner • Oceanfront • Bedding/Linens • Fireplace/Heating • Balcony/Terrace • Pet Friendly • Internet • View • Other • Laundry

Castaway Island Vacation Bungalow offers accommodations in Islamorada, 1.6 miles from Sea Oats Beach and 5.2 miles from Upper Matecumbe Key. Private parking is available on site at this recently renovated property. Pigeon Key is 18 miles from the villa and Florida Keys Aquarium Encounters is 24 miles away. With free Wifi, this 2-bedroom villa provides a flat-screen TV, a washing machine, and a fully equipped kitchen with a minibar. The accommodation is non-smoking. Theater of the Sea on Islamorada is 7.8 miles from the villa, while Windley Key is 8.3 miles away. Key West International Airport is 74 miles from the property.

Child Friendly • Pool • Pet Friendly • Security/Safety • Ev Charge Station • Internet • Parking • Air Conditioner

Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios 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.

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