Villas and Holiday homes in Islamorada, FL

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Islamorada, FL holiday homes
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528 Villa rentals in Islamorada, FL

Best Islamorada, FL villas and holiday homes with a pool

Among the 528 accommodations in Islamorada, FL, here are the 4 best villas and holiday homes with a pool

Marina To Ocean View Key Largo Ocean Pointe 5308 - Islamorada, FL
9.9 7 reviews

Marina To Ocean View Key Largo Ocean Pointe 5308

house, Tavernier
This Tavernier holiday home, Ocean Pointe 5308 in Key Largo, is situated near Harry Harris Park Beach (a 15-minute walk away) and within 18km of John Pennekamp Coral Reef State Park and Windley Key.
The 77-square-metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a swimming pool, jacuzzi, and fully equipped kitchen with dishwasher; free Wi-Fi and cable TV are also provided.
Keys Waterfront Condo Pool Beach And Views - Islamorada, FL
No reviews

Keys Waterfront Condo Pool Beach And Views

house, Tavernier
This holiday home is located in Tavernier, 2.1 kilometres from Harry Harris Park Beach and 4.8 kilometres from Pigeon Key.
This 86 square metre holiday home offers two bedrooms, two bathrooms and accommodates up to 10 guests with a kitchen, air conditioning, swimming pool, jacuzzi, and private balcony.
The Lighthouse- Ocean Views, Game Room, Pool ,Dock Access - Islamorada, FL
No reviews

The Lighthouse- Ocean Views, Game Room, Pool ,Dock Access

house, Islamorada, Village of Islands
This villa is located under 1 kilometre from Windley Key and an 8-minute walk to the Theater of the Sea in Islamorada, Village of Islands.
This 156 square metre holiday home sleeps 14 guests across 3 bedrooms and 4 bathrooms, featuring a swimming pool, spa, fitness centre, and sea views from the terrace.
Sirens Cove - Game Room, Pool - Dock Access - Islamorada, FL
No reviews

Sirens Cove - Game Room, Pool - Dock Access

house, Islamorada, Village of Islands
This oceanfront villa is located in the gated Peaceful Palms community in Islamorada, offering direct water access and partial ocean views from two balconies.
This dog-friendly holiday home accommodates up to eight guests, featuring three bedrooms and bathrooms, a private dock, a community pool, a Tiki hut bar, and a game room with a pool table and large television.

Best Islamorada, FL villas and holiday homes with a kitchen

Beautiful Bay And Beach Bungalow - Islamorada, FL
10 6 reviews

Beautiful Bay And Beach Bungalow

bungalow, Islamorada, Village of Islands
This bungalow is located in Islamorada, Village of Islands, offering direct access to Sea Oats Beach and the bay, with deep dockage for large boats. It has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
The bungalow has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and WiFi, as well as a spacious porch with stunning views.
Waterfront 2br, 2ba Islamorada Retreat With Pool, Hot Tub, And Kayaks. - Islamorada, FL
No reviews

Waterfront 2br, 2ba Islamorada Retreat With Pool, Hot Tub, And Kayaks.

house, Islamorada, Village of Islands
This pet-friendly villa in Islamorada's Seabreeze Trailer Park offers a prime waterfront position, situated 724 metres from Islamorada County Park and 884 metres from Founders Park, with convenient access to water sports and local eateries such as Hog Heaven.
This three-bedroom, two-bathroom holiday home accommodates up to six guests and features air conditioning, complimentary Wi-Fi, a fully equipped kitchen, a shared swimming pool, hot tub, and a balcony, ensuring a comfortable stay with on-site leisure facilities.
Keys Waterfront Condo With Beach Pool Sunset Views - Islamorada, FL
No reviews

Keys Waterfront Condo With Beach Pool Sunset Views

house, Tavernier
This holiday home in Tavernier is located a 13-minute walk from Harry Harris Park Beach and 4.8 kilometres from Pigeon Key.
This 86 square metre holiday home sleeps 11 guests with two bedrooms and two bathrooms, featuring a fridge, microwave, dishwasher, air conditioning, swimming pool, hot tub, balcony, garden, and parking.
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location - Islamorada, FL
9.5 2 reviews

Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

house, Islamorada, Village of Islands
This Isla Key Guava Boutique Resort villa in Islamorada, Florida Keys, boasts a prime waterfront location, a 12-minute walk from Upper Matecumbe Key and 4.3km from Windley Key.
The 156 square metre, three-bedroom property sleeps nine guests and features a fully equipped kitchen, swimming pool, fitness centre, and balcony with stunning views; free Wi-Fi and parking are also provided.

Frequently asked questions about villa rentals in Islamorada, FL

  • What are the must-see attractions in and around Islamorada, FL?

    Islamorada is known for its beautiful beaches and watersports, so you'll want to spend time on the sand or out on the water. The Theatre of the Sea is a popular attraction where you can see marine life shows and interact with dolphins. If you're interested in history, the Islamorada History Museum is a great place to learn about the area's past. And for a taste of local life, head to the Islamorada Arts & Crafts Village. You can also take a day trip to the nearby John Pennekamp Coral Reef State Park, where you can snorkel or dive among the colourful coral reefs.
  • What are the best villa rentals in Islamorada, FL?

    Among the villa rentals in Islamorada, FL, Conch Villa 4, 1 Bd Private Houseboat/ Cottage Tarpon and Serenity By The Sea Anglers Reef With Boat Slip Available are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Islamorada, FL?

    You'll see plenty of marine life in the waters around Islamorada, including dolphins, manatees, sea turtles, and a variety of fish. You might also spot some birds, like pelicans, herons, and osprey. If you're lucky, you might even see a few alligators in the freshwater canals and swamps.
  • What are the best villa rentals with a pool in Islamorada, FL?

    Conch Villa 4, Serenity By The Sea Anglers Reef With Boat Slip Available and Anglers Reef Paradise are the best villa rentals with a pool in Islamorada, FL.

  • What is the best time to visit Islamorada, FL?

    The best time to visit Islamorada is during the spring (March-May) or autumn (September-November) when the weather is warm and sunny, but not too humid. You'll find fewer crowds and more affordable prices during these shoulder seasons.
  • What are the best villa rentals with a jacuzzi in Islamorada, FL?

  • When is it easiest to book a villa rental in Islamorada, FL?

    You'll find the best deals on villa rentals in Islamorada during the off-season, which is generally from May to June and September to October. You'll also find less competition for rentals during these months.
  • What are the best villa rentals for families and kids in Islamorada, FL?

  • What are the top hiking trails near Islamorada, FL?

    There aren't many hiking trails in Islamorada itself, as it's a coastal town. However, if you're looking for some outdoor activity, you can head to the nearby John Pennekamp Coral Reef State Park which has a few nature trails. Or, you can drive about an hour north to the Everglades National Park, which has a wide variety of hiking trails.
  • What are the best pet friendly villa rentals in Islamorada, FL?

    The best pet friendly villa rentals in Islamorada, FL are Conch Villa 4, 1 Bd Private Houseboat/ Cottage Tarpon and Relax In Your Private Oceanfront Cottage.

  • What are the advantages of renting a house or a villa in Islamorada, FL

    Renting a villa gives you more space and privacy than a hotel room. You'll also have access to a kitchen, so you can cook your own meals. And if you're travelling with a group, you can all stay together in one place.
  • What are the best villa rentals with parking in Islamorada, FL?

  • Are there popular destinations near Islamorada, FL?

    Yes, there are plenty of popular destinations near Islamorada. You can take a day trip to Key West, which is about a 2-hour drive south. Or, you can head north to the Everglades National Park, which is about an hour away. You can also visit the Florida Keys Aquarium in Marathon, which is about 30 minutes south of Islamorada.

Popular destinations

Best Islamorada, FL villas and holiday homes with air conditioning

Bungalow #3 - 2 Bed/1 Bath & Pool In Islamorada - Islamorada, FL
9.6 85 reviews

Bungalow #3 - 2 Bed/1 Bath & Pool In Islamorada

apartment, Islamorada, Village of Islands
This charming cottage is situated in Islamorada, just a short distance from the Village of Islands' centre, offering easy access to fishing piers and the lively downtown area. It has received excellent ratings for location, cleanliness, and user experience, making it a great choice for a relaxing getaway.
The cottage comfortably sleeps four guests in two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private backyard, a community pool, a fully equipped kitchen, a washer and dryer, a private porch, and bikes for exploring the area.
Islamorada Getaway Townhouse - Islamorada, FL
9.7 26 reviews

Islamorada Getaway Townhouse

house, Islamorada, Village of Islands
This Islamorada townhouse, situated in the Village of Islands, is centrally located, minutes (less than 1.6km) from the Islamorada sandbar and acclaimed restaurants.
The three-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, private swimming pool, garden, and parking; note the spiral staircase.
Stay And Play Enjoy Scenic Views At Ocean Pointe 5312 - Islamorada, FL
No reviews

Stay And Play Enjoy Scenic Views At Ocean Pointe 5312

house, Tavernier
This holiday home in Tavernier is located a 13-minute walk from Harry Harris Park Beach and approximately 4.8 kilometres from Pigeon Key.
This property offers 86 square metres of living space with 2 bedrooms, 2 bathrooms, and accommodation for up to 10 guests, featuring a private swimming pool, hot tub, air conditioning, and a fully equipped kitchen.
Sirens Cove - Ocean Views, Game Room, Pool And Dock Access - Islamorada, FL
No reviews

Sirens Cove - Ocean Views, Game Room, Pool And Dock Access

house, Islamorada, Village of Islands
This holiday home in Sirens Cove, Islamorada, Village of Islands, is located under 1 kilometre from Windley Key and a 9-minute walk to the Theater of the Sea.
This 156 square metre, three-bedroom holiday home accommodates up to eight guests and features a kitchen, air conditioning, swimming pool, terrace, garden, spa, fitness centre, and games room, with parking available.

Best Islamorada, FL villas and holiday homes with jacuzzi

Charming & Tranquil Condo At Ocean Pointe-sleeps 6 - Islamorada, FL
No reviews

Charming & Tranquil Condo At Ocean Pointe-sleeps 6

house, Tavernier
This apartment is located in Ocean Pointe, Tavernier, a 13-minute walk from Harry Harris Park Beach and 4.8 kilometres from Pigeon Key.
With 86 square metres of living space, this two-bedroom, two-bathroom property accommodates up to 10 guests and features a fully equipped kitchen, air conditioning, a swimming pool, a hot tub, and free Wi-Fi.
Blue Haven Key Largoocean Pointe 1315 - Islamorada, FL
9.1 10 reviews

Blue Haven Key Largoocean Pointe 1315

house, Tavernier
Blue Haven Key Largo Ocean Pointe 1315, situated in Key Largo, offers stunning sunset views over Florida Bay and is a short drive (approx. 2.4km) from Harry Harris Park Beach.
This two-bedroom, two-bathroom property boasts 77 square metres of living space, a private patio, swimming pool, jacuzzi, and sleeps up to six guests, complete with a fully equipped kitchen, Wi-Fi, and cable TV.
Sunrise Suite With Unobstructed Ocean Views - Islamorada, FL
No reviews

Sunrise Suite With Unobstructed Ocean Views

house, Tavernier
This holiday home in Tavernier is located with unobstructed ocean views and is a 1.08-kilometre walk to Harry Harris Park Beach.
This spacious three-bedroom, two-bathroom property offers accommodation for up to 10 guests, featuring air conditioning, free WiFi, a fully equipped kitchen, a swimming pool, and a spa.
Tranquility On The Top Floor - Ocean Pointe 2404 - Islamorada, FL
No reviews

Tranquility On The Top Floor - Ocean Pointe 2404

house, Tavernier
This holiday apartment is located in Tavernier, 104 kilometres from Miami International Airport and a 13-minute walk from Harry Harris Park Beach.
This one-bedroom, one-bathroom property offers a fully equipped kitchen, air conditioning, a swimming pool, a hot tub, and a private balcony, with a guest capacity of six and a floor area of 70 square metres.
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