Islamorada, FL villas

Compare villa rentals in Islamorada, FL from 100+ providers!

336 available villa offers

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336 Villa rentals in Islamorada, FL

Superhost In Islamorada- A Tropical Paradise - - Islamorada, FL
9.7Excellent 79 reviews
Islamorada, FL
2 1
$333/nighttotal: $1332 (4 )

Superhost In Islamorada- A Tropical Paradise -

house - Islamorada, Village of Islands
Vacation rental for 2 guests with an excellent rating of 97% based on 79 reviews. You will stay in Islamorada, Village of Islands.
Services and facilities include a freeze, an iron and a washing machine. Take advantage of the air conditioning in this house!
Single Family Home In Angler's Reef Gated Community, Beaches,marina,heated Pool - Islamorada, FL
9.8Excellent 197 reviews
Islamorada, FL
2 2
$502/nighttotal: $3514 (7 )

Single Family Home In Angler's Reef Gated Community, Beaches,marina,heated Pool

house - Islamorada, Village of Islands
This Islamorada vacation house is a beachfront property offering stunning ocean views and easy access to the beach. Just a short drive away from top attractions like Windley Key Fossil Reef Geological State Park, it boasts excellent user, location, and cleanliness ratings.
The house features a spacious 1600 square foot floor plan with 2 bedrooms and a guest capacity of 6. Guests can enjoy a fully equipped kitchen, multiple bathrooms for convenience, a private balcony, and a spa tub. The property also includes a barbecue grill, washing machine, and plenty of parking.
Serene Cozy Cottage In Islamorada With Heated Pool - Islamorada, FL
9.6Excellent 111 reviews
Islamorada, FL
2 2
$447/nighttotal: $1788 (4 )

Serene Cozy Cottage In Islamorada With Heated Pool

cottage - Islamorada, Village of Islands
This cottage is located in the heart of Islamorada, Village of Islands, at mile marker 76.7, a short distance from Robbie's Marina (3.2 miles) and Caloosa Cove Marina (3.2 miles). It has excellent user ratings for location, cleanliness, and overall experience.
The charming cottage has two private bedrooms accommodating up to 4 guests, a fully stocked kitchen, a spacious living area, and access to a communal, heated swimming pool. It also offers a private driveway parking for two cars, a pack n play crib and highchair available upon request (48-hour notice required), and a starter pack of essential supplies provided for a comfortable stay.
Relax In Your Private Oceanfront Cottage! - Islamorada, FL
10Excellent 92 reviews
Islamorada, FL
2 1
$309/nighttotal: $2163 (7 )

Relax In Your Private Oceanfront Cottage!

cottage - Islamorada, Village of Islands
This oceanfront cottage is situated in Matecumbe, a neighborhood in Islamorada, Village of Islands, offering easy access to nearby attractions. It has excellent user ratings and features one bedroom and one bathroom.
The cottage has been newly renovated and decorated with modern and stylish interior, all new appliances and furnishings. It includes amenities like a private boat dock and ramp, kayaks and bicycles, a tiki hut, and fishing charter options.
Serenity By The Sea!!  Anglers Reef With Boat Slip Available!! - Islamorada, FL
10Excellent 101 reviews
Islamorada, FL
2 2
$446/nighttotal: $3122 (7 )

Serenity By The Sea!! Anglers Reef With Boat Slip Available!!

house - Islamorada, Village of Islands
House listing from $349 for 6 people with an excellent rating of 100% based on 101 reviews. Your accommodation will be based in Islamorada, Village of Islands.
Facilities and services: a washing machine, a barbecue and air conditioning. This is a pet-friendly house!
Anglers Reef Islamorada  Home With Ocean Views, Private Marina, Beach & Pool - Islamorada, FL
10Excellent 111 reviews
Islamorada, FL
2 2
$443/nighttotal: $3101 (7 )

Anglers Reef Islamorada Home With Ocean Views, Private Marina, Beach & Pool

house - Islamorada, Village of Islands
House listing with an excellent rating of 100% based on 111 reviews. You will be based in Islamorada, Village of Islands.
Facilities and services include a dish washer, a swimming pool and air conditioning. Take advantage of the garden in this house in Islamorada, Village of Islands.
Bayside: 1st Floor Apartment In Native Hammock On Florida Bay - Islamorada, FL
9.7Excellent 81 reviews
Islamorada, FL
2 1
$338/nighttotal: $2366 (7 )

Bayside: 1st Floor Apartment In Native Hammock On Florida Bay

house - Islamorada, Village of Islands
House rental listing for up to 4 guests with an excellent rating of 97% based on 81 reviews. You will be based in Islamorada, Village of Islands.
Facilities and services: a jacuzzi, a washing machine and a dish washer. This house in Islamorada, Village of Islands is ideal for families.
Mitchells Keys Villa - Private, Secluded Bayfront Home - Islamorada, FL
9.7Excellent 96 reviews
Islamorada, FL
2 1
$406/nighttotal: $2842 (7 )

Mitchells Keys Villa - Private, Secluded Bayfront Home

house - Islamorada, Village of Islands
House listing with an excellent rating of 97% based on 96 reviews. You will be based in Islamorada, Village of Islands.
Services and facilities include free parking, a washing machine and a spa. Take a dip in the pool of this house in Islamorada, Village of Islands!
Islamorada Anglers Reef! “Sandbar Bungalow Villa" Amazing! Middle Row Location! - Islamorada, FL
9.8Excellent 278 reviews
Islamorada, FL
2 2
$502/nighttotal: $3514 (7 )

Islamorada Anglers Reef! “Sandbar Bungalow Villa" Amazing! Middle Row Location!

house - Islamorada, Village of Islands
This Islamorada vacation home is nestled on the beach, within 3 miles of Windley Key Fossil Reef Geological State Park, Founders Park, and Islamorada County Park. It offers a beachfront location with direct access to the ocean and has an excellent user rating.
The house has 2 bedrooms with a sofa bed for additional sleeping capacity, accommodating up to 6 guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, and parking. Guests can enjoy water activities, relax on the beach, or explore nearby tourist attractions.
Keys Kottage; Remodeled Villa In Native Hammock On Florida Bay - Islamorada, FL
9.9Excellent 180 reviews
Islamorada, FL
2 2
$339/nighttotal: $2373 (7 )

Keys Kottage; Remodeled Villa In Native Hammock On Florida Bay

house - Islamorada, Village of Islands
Accommodation for 4 people with an excellent rating of 99% based on 180 reviews. You will be based in Islamorada, Village of Islands.
Facilities and services: a tennis court, a barbecue and an iron. This house also has a terrace!
Anglers Reef Islamorada Oceanside Gated Community - 2/2.5, Marina, Pool, & Beach - Islamorada, FL
10Excellent 101 reviews
Islamorada, FL
2 2
$375/nighttotal: $2625 (7 )

Anglers Reef Islamorada Oceanside Gated Community - 2/2.5, Marina, Pool, & Beach

house - Islamorada, Village of Islands
House for 6 people with an excellent rating of 100% based on 101 reviews. You will be based in Islamorada, Village of Islands.
Services and facilities include a fridge, air conditioning and a kitchen. Take advantage of the garden in this house!
Immaculate Oceanfront Villa With Resort Amenities - Islamorada, FL
10Excellent 4 reviews
Islamorada, FL
2 4
$2588/nighttotal: $10352 (4 )

Immaculate Oceanfront Villa With Resort Amenities

house - Islamorada, Village of Islands
This Islamorada waterfront villa is located in the tranquil Village of Islands neighborhood, offering privacy and exclusivity for guests seeking a peaceful retreat. The villa boasts an excellent user rating and is just a short distance from the Florida Keys Brewing Co. and Bud n' Mary's Dive Center.
The spacious villa features four bedrooms, five bathrooms, full kitchens, and ample living and dining spaces, providing comfortable accommodations for up to eight guests. The 4070-square-foot floor area offers plenty of room to relax and unwind. Guests can enjoy breathtaking ocean views from multiple outdoor lounge areas, as well as access to a private marina, pools, Jacuzzi, fitness pavilion, and various outdoor activities, including watersports, pickleball, and bocce.

Other accommodation types in Islamorada, FL

Best Islamorada, FL villas and beach houses with a pool

Among the 336 accommodations in Islamorada, FL, here are the 8 best villas and beach houses with a pool

Islamorada Oceanfront Home With Ocean View, Dock, Comm Pool & Beach - Islamorada, FL
10Excellent 164 reviews
Islamorada, FL
2 2
$681/nighttotal: $4767 (7 )

Islamorada Oceanfront Home With Ocean View, Dock, Comm Pool & Beach

house - Islamorada, Village of Islands
This **beachfront vacation home** in Islamorada, Village of Islands is located within 3 miles of Windley Key Fossil Reef Geological State Park and other popular landmarks. It has an excellent user rating.
The house has 2 bedrooms, 3 bathrooms, a fully equipped kitchen, and a private balcony. It can accommodate up to 6 guests and has a floor area of 1700 square feet. Amenities include a swimming pool, terrace, garden, parking, air conditioning, internet, and barbecue grills. Pets are allowed.
Tiki Bar,heated Pool,pri Spa, Kayaks,sup’s,bikes,bbq,fire Ring, Outside Tv, More - Islamorada, FL
10Excellent 169 reviews
Islamorada, FL
2 2
$666/nighttotal: $4662 (7 )

Tiki Bar,heated Pool,pri Spa, Kayaks,sup’s,bikes,bbq,fire Ring, Outside Tv, More

house - Islamorada, Village of Islands
This house is situated by the sea in Islamorada, Village of Islands, within 2 miles of San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park. It has excellent user, location and cleanliness ratings.
The house is suitable for families and groups, with 2 bedrooms and a guest capacity of 5. It includes a cozy interior with a fireplace, a fully equipped kitchen with a refrigerator and an oven, and a balcony. Guests can also enjoy amenities such as a water park, outdoor pool, spa tub, concierge services, a garden, and barbecue grills.
Venetian Tropics Weekly Pvt Home W/heated Pool, 3 Bedroom /70ft Dock W/canal - Islamorada, FL
9.6Excellent 86 reviews
Islamorada, FL
2 3
$810/nighttotal: $5670 (7 )

Venetian Tropics Weekly Pvt Home W/heated Pool, 3 Bedroom /70ft Dock W/canal

house - Islamorada, Village of Islands
This Venetian Shores vacation home is nestled on the beach in Islamorada, within 2 km of Founders Park and Islamorada County Park, making it a perfect base for exploring the area. With an excellent user rating, this beachfront home offers stunning ocean views and a private pool for exclusive use.
The house boasts 3000 square feet of living space, 3 bedrooms, 4 bathrooms, and can accommodate up to 8 guests. Amenities include a fully equipped kitchen, complimentary WiFi, DVD player, air conditioning, and a terrace/balcony with barbecue grills for relaxation and entertainment.
Spectacular Ocean Front Home In Beautiful Islamorada!<br>dock,com Pool, & Prv Beach - Islamorada, FL
10Excellent 56 reviews
Islamorada, FL
2 2
$798/nighttotal: $5586 (7 )

Spectacular Ocean Front Home In Beautiful Islamorada!<br>dock,com Pool, & Prv Beach

house - Islamorada, Village of Islands
House to rent with an excellent rating of 100% based on 56 reviews. You will be in Islamorada, Village of Islands.
Services and facilities include free parking, a dish washer and a kitchen. Take advantage of the pool in this house.
Cozy 2-bedroom Villa With Resort Amenities - Islamorada, FL
9.3Excellent 24 reviews
Islamorada, FL
4 1
$1281/nighttotal: $3843 (3 )

Cozy 2-bedroom Villa With Resort Amenities

house - Islamorada, Village of Islands
This Islamorada, Village of Islands house with excellent ratings is perfect for a family vacation. It has 2 bathrooms and accommodates 4 guests.
The house features a kitchen with a fridge, air conditioning, a swimming pool, a garden, parking, and allows pets. It also has internet access.
Islamorada Anglers Reef ~ Stay In Paradise For Your Next Vacation - Islamorada, FL
10Excellent 66 reviews
Islamorada, FL
2 2
$390/nighttotal: $2730 (7 )

Islamorada Anglers Reef ~ Stay In Paradise For Your Next Vacation

house - Islamorada, Village of Islands
This oceanfront vacation home in Islamorada, Village of Islands, is a perfect choice for travelers seeking a relaxing and entertaining getaway. It's just 2 miles from Windley Key Fossil Reef Geological State Park and Founders Park, and has excellent user, location, and cleanliness ratings.
The 2-bedroom house accommodates up to 6 guests and offers a fully equipped kitchen, outdoor pool, spa tub, barbecue grills, and free WiFi. It also features a sofa bed for additional sleeping arrangements, a terrace/balcony, a garden, and parking.
Beachside 3-bedroom Villa With Private Yard - Islamorada, FL
9.3Excellent 9 reviews
Islamorada, FL
4 3
$1224/nighttotal: $3672 (3 )

Beachside 3-bedroom Villa With Private Yard

house - Islamorada, Village of Islands
Seaglass is a 3-bedroom, 3-bathroom vacation house located just steps from the beach in Islamorada, Village of Islands. Guests have access to a range of resort amenities, including paddleboards, kayaks, bikes, and a poolside bar.
Seaglass has been rated excellent by previous guests for its location, cleanliness, and amenities. The house has a spacious layout with two family rooms and a wrap-around patio with an enclosed yard. It can accommodate up to 8 guests. The fully-equipped kitchen and access to resort amenities make Seaglass an ideal choice for families and groups looking for a comfortable and convenient vacation rental.
Islamorada House In Front Of Sand Bar - Islamorada, FL
9.8Excellent 8 reviews
Islamorada, FL
2 2
$560/nighttotal: $3920 (7 )

Islamorada House In Front Of Sand Bar

house - Islamorada, Village of Islands
This oceanfront house is located in a peaceful community with a beautiful pool overlooking the Atlantic Ocean. It offers private beach access with kayaks available for launch.
The house has two bedrooms with private bathrooms on the second floor, a fully equipped kitchen with stainless steel appliances, granite counters, 3 TVs, and WiFi. It can accommodate up to 6 guests and has parking for two vehicles.

Best family friendly Islamorada, FL villas and beach houses

Among the 336 accommodations in Islamorada, FL, here are the 7 best family friendly villas and beach houses

149 M² House ∙ 3 Bedrooms ∙ 8 Guests - Islamorada, FL
Islamorada, FL
2 3
$646/nighttotal: $4522 (7 )

149 M² House ∙ 3 Bedrooms ∙ 8 Guests

house - Islamorada, Village of Islands
This 3-bedroom Islamorada, Village of Islands house is perfect for a family vacation. It has a spacious floor plan with 1600 square feet of living space and can accommodate up to 8 guests.
The house is fully equipped with a kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking. It also has internet access, making it easy to stay connected during your stay.
Angler’s Reef House. Paddle Or Kayak To Sandbar. Lic #24-0055 - Islamorada, FL
10Excellent 17 reviews
Islamorada, FL
2 2
$608/nighttotal: $4256 (7 )

Angler’s Reef House. Paddle Or Kayak To Sandbar. Lic #24-0055

house - Islamorada, Village of Islands
This waterfront villa is located in Islamorada, Village of Islands, just 0.4 miles from Windley Key Fossil Reef Geological State Park and within 3 miles of Founders Park and Islamorada County Park. It has excellent user ratings.
The villa has two spacious bedrooms, three bathrooms, and can accommodate up to six guests. It features a fully equipped kitchen, free WiFi, a sofa bed, and a smoke-free environment. Guests can enjoy swimming in the private outdoor pool, sunbathing in the garden, and grilling on the barbecue.
Charming Key Lime Cottage W Pool Great Location - Islamorada, FL
9.9Excellent 52 reviews
Islamorada, FL
2 2
$397/nighttotal: $2779 (7 )

Charming Key Lime Cottage W Pool Great Location

cottage - Islamorada, Village of Islands
The Key Lime Cottage is located in the heart of Islamorada, Village of Islands, just 5 minutes from Founders Park and Annes Beach. It has excellent user, location, and cleanliness ratings.
The cottage has 2 bedrooms and 1 bathroom and can accommodate up to 5 guests. It features a full kitchen, access to a shared pool, outside seating with a grill and a fire pit, beach chairs, key lime treats, and air conditioning.
Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 4 - Islamorada, FL
9.9Excellent 23 reviews
Islamorada, FL
2 2
$528/nighttotal: $3696 (7 )

Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 4

cottage - Islamorada, Village of Islands
This fully remodeled 2-bedroom cottage is located in the heart of Islamorada, Village of Islands. Just steps from the community heated pool, this cottage is perfect for a private retreat. With excellent user, location, and cleanliness ratings, this cottage is a great choice for travelers.
The cottage has a floor area of 950 square feet and can accommodate up to four guests. It features a private backyard and parking, a fully equipped kitchen, a private porch, and in-unit washer and dryer. Guests can also enjoy basic amenities such as a stove, fridge, coffee machine, and toaster. Bicycles are also available on site for guests to explore the island at their leisure.
173 M² House ∙ 3 Bedrooms ∙ 6 Guests - Islamorada, FL
Islamorada, FL
2 3
$1157/nighttotal: $8099 (7 )

173 M² House ∙ 3 Bedrooms ∙ 6 Guests

house - Islamorada, Village of Islands
This Islamorada house is located in the Village of Islands, a family-friendly area with a relaxed ambiance, and just a short distance from the beach.
The house has 3 bedrooms and can accommodate up to 6 guests. It has a floor area of 1860 square feet and features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking.
372 M² House ∙ 5 Bedrooms ∙ 12 Guests - Islamorada, FL
Islamorada, FL
2 5
$550/nighttotal: $1650 (3 )

372 M² House ∙ 5 Bedrooms ∙ 12 Guests

house - Islamorada, Village of Islands
This spacious 5-bedroom, 4-bathroom house in Islamorada, Village of Islands, is perfect for families and groups of up to 12 guests. It is located within walking distance of restaurants and grocery stores, and just minutes from the ocean by boat. The house offers wrap-around porches on two levels with views of the canal, providing a serene and picturesque setting.
The house has a floor area of 3990 square feet and comes with two kayaks and two bikes, allowing guests to explore the surrounding area. It also features a fitness center, tennis court, and dock space for a 40-foot boat or less. The house is fully equipped with a kitchen, dining area, and bathrooms, and includes amenities such as AC/heat, wireless internet, and a washer/dryer.
The Villa By The Bay Unit #2 - Islamorada, FL
Islamorada, FL
2 4
$1221/nighttotal: $8547 (7 )

The Villa By The Bay Unit #2

house - Islamorada, Village of Islands
This 4-bedroom, 4-bathroom vacation home is located in a gated community on the Florida Bay in Islamorada, Village of Islands. It is within close proximity to world-famous restaurants and Islamorada nightlife.
This spacious home can accommodate up to 9 guests and features a fully equipped kitchen, air conditioning, Wi-Fi, a washer and dryer, a private plunge pool, a community pool on the bay, boat dockage, and boat trailer storage.

Frequently asked questions about villa rentals in Islamorada, FL

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Best pet friendly Islamorada, FL villas and beach houses

Among the 336 accommodations in Islamorada, FL, here are the 3 best pet friendly villas and beach houses

By The Sea ~ Islamorada Home With Ocean Views! - Islamorada, FL
9.4Excellent 12 reviews
Islamorada, FL
2 2
$478/nighttotal: $3346 (7 )

By The Sea ~ Islamorada Home With Ocean Views!

house - Islamorada, Village of Islands
This vacation home is located in the tranquil Matecumbe district of Islamorada, Village of Islands, within walking distance of Sunset Drive Beach and San Pedro Underwater Archaeological Preserve State Park. The house has received excellent user ratings.
The house has 2 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. It features a fully equipped kitchen, a private balcony, a garden, and air conditioning. Guests can enjoy activities such as swimming, sunbathing, water sports, and diving.
Charming Canal-front House | Wifi+swim+kayak+fish - Islamorada, FL
Islamorada, FL
2 4
$922/nighttotal: $3688 (4 )

Charming Canal-front House | Wifi+swim+kayak+fish

house - Tavernier
This 4-bedroom vacation rental in the tranquil Blue Waters neighborhood is the ideal retreat for families or groups. Just 1 mile from the beautiful beach and amenities of Baker's Cay Resort, this spacious home offers a peaceful escape while still being close to popular tourist destinations.
The fully equipped kitchen, free WiFi, and balcony provide all the comforts of home, while the outdoor barbecue grills and smoke-free environment make for a relaxing and enjoyable stay.
Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 3 - Islamorada, FL
9.5Excellent 26 reviews
Islamorada, FL
4 2
$570/nighttotal: $1710 (3 )

Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 3

cottage - Islamorada, Village of Islands
This fully remodeled 2-bedroom, 1-bathroom cottage is located in the heart of Islamorada, Village of Islands, just steps away from the community heated pool. With excellent user, location, and cleanliness ratings, this cottage offers a comfortable and convenient stay for up to 4 guests.
The cottage features a private backyard and parking, a fully remodeled interior, two queen-size bedrooms, an in-unit washer and dryer, a private porch, bicycles on site, and a security camera at the entrance. Guests can enjoy the tranquility of their own outdoor space, take a refreshing dip in the heated pool, and explore the surrounding area with complimentary bicycles.