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

Catch The Day Toast The Night- Fish Dive & Island Vibes - Islamorada, FL
No reviews

Catch The Day Toast The Night- Fish Dive & Island Vibes

house, Tavernier
This holiday rental in Tavernier is a 13-minute walk from Harry Harris Park Beach, 4.8 kilometres from Pigeon Key, and 13.9 kilometres from the Theater of the Sea on Islamorada.
This 86 square metre, two-bedroom, two-bathroom holiday home accommodates up to 10 guests and features a swimming pool, hot tub, garden with seating, and complimentary WiFi in public areas.
Flamingo Flats Ocean Pointe 5306 - Islamorada, FL
9.8 6 reviews

Flamingo Flats Ocean Pointe 5306

house, Tavernier
Flamingo Flats Ocean Pointe 5306, situated in Key Largo, offers convenient access to Harry Harris Park Beach (a 2.4km walk), Pigeon Key (4.5km), and Windley Key Fossil Reef Geological State Park (14.3km).
This two-bedroom, two-bathroom property boasts 77 square metres of living space, sleeps six guests, and includes a private patio with ocean views, a swimming pool, Jacuzzi, and fully equipped kitchen with dishwasher.
Secluded Beach And Heated Pool - Stunning Waterfront Haven - Islamorada, FL
No reviews

Secluded Beach And Heated Pool - Stunning Waterfront Haven

house, Islamorada, Village of Islands
This oceanfront residence is located directly on a secluded beach in Islamorada, Village of Islands, offering direct access to the water and a private stretch of sand.
This spacious villa accommodates up to 10 guests and features a heated swimming pool, a private dock, high-speed Gigabit Wi-Fi, and gourmet eat-in kitchen with uninterrupted ocean views.
Bay Front With Tropical Charm - Luxury Island Beach House Oasis - Islamorada, FL
No reviews

Bay Front With Tropical Charm - Luxury Island Beach House Oasis

house, Islamorada, Village of Islands
This Islamorada shore front property offers a luxurious six-bedroom, six-bathroom villa for up to 12 guests on nearly 0.4 hectares of manicured grounds, providing direct beach access.
Guests can enjoy air conditioning, a fully equipped kitchen with a microwave and dishwasher, a swimming pool, fitness centre, tennis court, and parking, with pets and families welcome.

Best Islamorada, FL villas and holiday homes with a kitchen

Oceanside Family Condo With Pool And Beach Access - Islamorada, FL
No reviews

Oceanside Family Condo With Pool And Beach Access

house, Tavernier
This oceanside apartment in Tavernier is a 13-minute walk from Harry Harris Park Beach and approximately 4.8 kilometres from Pigeon Key, with Miami International Airport 104.6 kilometres away.
This spacious two-bedroom, two-bathroom condominium offers sea views from its balcony, direct beach access, an outdoor swimming pool, an on-site spa, and free WiFi in public areas, accommodating up to 11 guests.
Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3br With Private Bathrooms - Islamorada, FL
10 2 reviews

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3br With Private Bathrooms

house, Islamorada, Village of Islands
This direct oceanfront luxury property in Islamorada, Village of Islands, is located 4.66 kilometres from Upper Matecumbe Key and is an 11-minute walk from Windley Key and a 9-minute walk from Theater of the Sea.
This 223 square metre, 3-bedroom holiday home accommodates up to 15 guests and features a speakeasy lounge, dock, swimming pool, garden, fitness centre, and an indoor play area, with complimentary WiFi, bikes, and private parking provided.
Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable - Islamorada, FL
No reviews

Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

house, Islamorada, Village of Islands
This waterfront boutique resort, Isla Honeydew, is situated in Islamorada, Village of Islands, a 12-minute walk from Upper Matecumbe Key and 3.4 kilometres from the Theater of the Sea.
This air-conditioned three-bedroom villa offers accommodation for six guests, featuring a heated swimming pool, a garden, a children's playground, and a private balcony, with on-site amenities including free Wi-Fi and a fully equipped kitchen.
Waterfront Sunset View Aqua Villa At Sea Biscuit @ Mangrove Resort Llc - Islamorada, FL
9.5 52 reviews

Waterfront Sunset View Aqua Villa At Sea Biscuit @ Mangrove Resort Llc

house, Tavernier
This waterfront houseboat resort in Tavernier is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Mariners Hospital, offering easy access to both relaxation and healthcare. The resort boasts excellent user ratings and very good scores for location and cleanliness, ensuring a pleasant stay.
The 46 square metre houseboat features a comfortable layout with one bathroom, perfect for a couple or small family. Guests can enjoy a range of amenities, including a swimming pool, barbecue grills, and a tranquil garden, making it ideal for a relaxing getaway.

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

158 M² House ∙ 3 Bedrooms ∙ 8 Guests - Islamorada, FL
No reviews

158 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Islamorada, Village of Islands
This Islamorada residence offers direct ocean access via Tavernier Creek, placing you minutes from premier sport fishing, snorkelling, diving, and sandbar excursions.
This 158 square meter holiday home accommodates up to eight guests with three bedrooms and three bathrooms, featuring a private heated and chilled pool, hot tub, over 60 feet of private dockage, and an outdoor Weber grill.
118 M² House ∙ 3 Bedrooms ∙ 6 Guests - Islamorada, FL
10 1 review

118 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Islamorada, Village of Islands
This Islamorada villa is located on the Gulf side, offering direct canal access with deep water and a private boat ramp, ideal for boating enthusiasts.
This 118 square metre property accommodates up to six guests with three bedrooms and two bathrooms, featuring a fully renovated kitchen, screened-in porch, and covered parking.
Beautiful Venetian Shores, Cozy Home, Heated Pool, Tiki, Boat Lift, Fish & Dive. - Islamorada, FL
10 6 reviews

Beautiful Venetian Shores, Cozy Home, Heated Pool, Tiki, Boat Lift, Fish & Dive.

house, Islamorada, Village of Islands
This Islamorada villa is situated in Venetian Shores, less than 3.2km from Rain Barrel Village, Islamorada County Park, Founders Park, and Windley Key Fossil Reef Geological State Park.
The 182 square metre property boasts three bedrooms, three bathrooms, sleeps six, and includes a private pool, barbecue, fully equipped kitchen, and laundry facilities.
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 jacuzzi

Ocean View Gem Ocean Pointe 3406 - Islamorada, FL
8.9 16 reviews

Ocean View Gem Ocean Pointe 3406

house, Tavernier
Ocean View Gem Ocean Pointe 3406, a two-bedroom house in Key Largo, offers easy access to Harry Harris Park Beach (2km), Pigeon Key (5km), Windley Key (13km), and John Pennekamp State Park (18km).
This 77 square metre property boasts a private patio with pool access, a fully equipped kitchen, two bathrooms, sleeps seven guests, and includes free Wi-Fi, cable TV, and a washing machine.
Cuda Point - Islamorada, FL
No reviews

Cuda Point

house, Key Largo
This Key Largo holiday home, Cuda Point, is situated 1km from Pigeon Key and within 13-23km of John Pennekamp Coral Reef State Park, Windley Key, and Upper Matecumbe Key, offering easy access to local attractions.
The 399 square metre property boasts three bedrooms, three bathrooms, and accommodates up to 27 guests, featuring a swimming pool, jacuzzi, fully equipped kitchen, and free Wi-Fi; enjoy ocean views and proximity to the History of Diving Museum (19km).
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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