Villas and Holiday homes in Islamorada, FL

522 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Islamorada, FL holiday homes
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

522 Villa rentals in Islamorada, FL

Best Islamorada, FL villas and holiday homes with a pool

Among the 522 accommodations in Islamorada, FL, here are the 4 best villas and holiday homes with a pool

Islamorada Beach - Beachfront, Fire Pit & Pool - Islamorada, FL
Islamorada, FL
27/06 – 04/07
2682 €/nighttotal: 18774 € (7 )

Islamorada Beach - Beachfront, Fire Pit & Pool

6 2
house , Islamorada, Village of Islands
This beachfront property in Islamorada, Village of Islands, offers direct access to a private beach and is located 1.8 kilometres from the Theater of the Sea and 2.6 kilometres from Windley Key.
This spacious six-bedroom holiday home accommodates up to twenty-three guests, featuring a private outdoor swimming pool, a well-equipped kitchen, five bathrooms, a terrace with sea views, an outdoor dining area, and complimentary WiFi and parking.
Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location - Islamorada, FL
Islamorada, FL
07/08 – 23/08
424 €/nighttotal: 6784 € (16 )

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

3 4
house , Islamorada, Village of Islands
Isla Key Lychee, a waterfront villa in Islamorada, offers easy access to Upper Matecumbe Key (a 2km walk) and Windley Key (4km), with Pigeon Key and John Pennekamp Coral Reef State Park further away.
This three-bedroom, three-bathroom property boasts 156 square metres of living space, comfortably accommodating nine guests and featuring a fully equipped kitchen, private balcony, swimming pool, fitness centre, free Wi-Fi, and on-site parking.
Flamingo Flats Ocean Pointe 5306 - Islamorada, FL
9.6 5 reviews
Islamorada, FL
07/08 – 23/08
251 €/nighttotal: 4016 € (16 )

Flamingo Flats Ocean Pointe 5306

2 4
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.
Isla Lychee: Boutique Resort, Free Boat Dockage Sep-oct Only! - Islamorada, FL
10 7 reviews
Islamorada, FL
07/08 – 23/08
423 €/nighttotal: 6768 € (16 )

Isla Lychee: Boutique Resort, Free Boat Dockage Sep-oct Only!

3 4
house , Islamorada, Village of Islands
Isla Lychee: Little Basin Villas, a waterfront boutique resort in Matecumbe, Islamorada, is within walking distance of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and less than 2.4km from the History of Diving Museum.
This 156 square metre, three-bedroom villa sleeps six, offering four bathrooms, a fully equipped kitchen, free Wi-Fi, a private balcony, and access to on-site barbecue grills.

Best Islamorada, FL villas and holiday homes with a kitchen

Private Beach/ocean Front Villa: Keys Island Life! - Islamorada, FL
Islamorada, FL
01/01 – 31/05
736 €/nighttotal: 110400 € (150 )

Private Beach/ocean Front Villa: Keys Island Life!

1 2
house , Islamorada, Village of Islands
This beachfront villa in Islamorada, Village of Islands, boasts direct beach access on a 1.2-hectare plot, offering proximity to local marinas but precise distances to specific landmarks remain unspecified.
Sleeping up to 14 guests, this five-bedroom, three-bathroom property features two living rooms, two outdoor showers, a fully equipped kitchen with an island and wine fridge, a huge outdoor kitchen, two laundry rooms, and private balconies with ocean views from each bedroom; a fitness centre is also on-site.
Heavenly Hideaway Ocean Pointe 3306 - Islamorada, FL
10 1 review
Islamorada, FL
17/07 – 24/07
289 €/nighttotal: 2023 € (7 )

Heavenly Hideaway Ocean Pointe 3306

2 3
house , Tavernier
Heavenly Hideaway Ocean Pointe 3306, a two-bedroom house in Tavernier, Florida, offers ocean views and is a short walk (less than 2km) from Harry Harris Park Beach, with Pigeon Key (4.5km), Windley Key Fossil Reef Geological State Park (14.3km), and John Pennekamp Coral Reef State Park (17.7km) also within easy reach.
This 80 square metre property sleeps eight guests and boasts a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, garden, parking, and in-unit laundry facilities; perfect for a self-catering holiday.
Isla Mamey: Free Boat Dockage Sept-oct Only! - Islamorada, FL
10 7 reviews
Islamorada, FL
17/07 – 24/07
563 €/nighttotal: 3941 € (7 )

Isla Mamey: Free Boat Dockage Sept-oct Only!

3 3
house , Islamorada, Village of Islands
Isla Mamey Villa #5, situated in Islamorada's Art District, offers easy walking access to shops, restaurants, and parks, and is within a few kilometres of attractions such as Robbie's Marina and Theatre of the Sea.
This three-bedroom, three-bathroom upscale villa sleeps six guests, boasting a fully equipped kitchen, private deck with partial water views, and access to a community pool and BBQ area; 24/7 guest support is also provided.
Marina To Ocean View Key Largo Ocean Pointe 5308 - Islamorada, FL
9.8 6 reviews
Islamorada, FL
17/07 – 24/07
282 €/nighttotal: 1974 € (7 )

Marina To Ocean View Key Largo Ocean Pointe 5308

1 3
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.

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.

Destinations nearby

Best Islamorada, FL villas and holiday homes with air conditioning

Blue Haven Key Largoocean Pointe 1315 - Islamorada, FL
9.3 9 reviews
Islamorada, FL
17/07 – 24/07
275 €/nighttotal: 1925 € (7 )

Blue Haven Key Largoocean Pointe 1315

2 3
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.
Oceanfront Islamorada Townhome With Pool & Dock - Islamorada, FL
10 8 reviews
Islamorada, FL
07/08 – 23/08
491 €/nighttotal: 7856 € (16 )

Oceanfront Islamorada Townhome With Pool & Dock

1 4
house , Islamorada, Village of Islands
This three-bedroom, three-bathroom house in Islamorada, Village of Islands, offers comfortable accommodation for up to eight guests and includes a swimming pool, garden, and parking.
The property boasts a fully equipped kitchen, air conditioning, and internet access, providing a relaxing base for exploring the Florida Keys, although precise distances to local attractions require further clarification.
Little Bay Cottage - Islamorada, FL
Islamorada, FL
17/07 – 24/07
601 €/nighttotal: 4207 € (7 )

Little Bay Cottage

2 3
house , Islamorada, Village of Islands
Little Bay Cottage, a two-bedroom house in Islamorada, offers convenient access to Upper Matecumbe Key, Windley Key (4.3km), and Pigeon Key (21km), with John Pennekamp Coral Reef State Park a further 32km away.
This self-catering property sleeps seven, boasting a fully equipped kitchen with dishwasher, air conditioning, a spa, fitness centre, free Wi-Fi, in-unit laundry, and on-site parking.
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable - Islamorada, FL
10 1 review
Islamorada, FL
07/08 – 23/08
415 €/nighttotal: 6640 € (16 )

Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

3 4
house , Islamorada, Village of Islands
This Islamorada waterfront villa, a short walk from Upper Matecumbe Key and within 4.3km of Windley Key, offers easy access to local shops, restaurants, and major attractions including Pigeon Key (21km) and John Pennekamp Coral Reef State Park (34km).
The 156 square metre property boasts three bedrooms, three bathrooms, sleeps nine guests, and includes a heated pool, private dock, free Wi-Fi, and on-site parking.

Best Islamorada, FL villas and holiday homes with jacuzzi

Sunshine Paradise Key Largo Ocean Pointe 4402 - Islamorada, FL
10 2 reviews
Islamorada, FL
07/08 – 23/08
253 €/nighttotal: 4048 € (16 )

Sunshine Paradise Key Largo Ocean Pointe 4402

2 4
house , Tavernier
Sunshine Paradise Key Largo Ocean Pointe 4402, a two-bedroom house in Tavernier, Key Largo, offers oceanfront proximity, a 15-minute walk from Harry Harris Park Beach, and is 4.5km from Pigeon Key and 13km from Windley Key.
This 77-square-metre property boasts two bathrooms, sleeps seven guests, and includes a private entrance, swimming pool, Jacuzzi, free Wi-Fi, and a fully equipped kitchen with dishwasher; in-unit laundry facilities are also provided.
It's Island Time In The Keys Double King Ensuites 2 Balconies - Islamorada, FL
10 1 review
Islamorada, FL
06/08 – 09/08
416 €/nighttotal: 1248 € (3 )

It's Island Time In The Keys Double King Ensuites 2 Balconies

2 2
house , Tavernier
This Key Largo holiday home is situated a 15-minute walk from Harry Harris Park Beach, 4.5km from Pigeon Key, and within 18km of Upper Matecumbe Key and Windley Key Fossil Reef Geological State Park.
This 77 square metre property boasts two king-size ensuite bedrooms, two balconies, a fully equipped kitchen, private garden, swimming pool, Jacuzzi, parking and accommodates up to eight guests.
Key Largo Oceanfront Oasis With Pool And Hot Tub - Islamorada, FL
8.0 3 reviews
Islamorada, FL
19/08 – 21/08
613 €/nighttotal: 1226 € (2 )

Key Largo Oceanfront Oasis With Pool And Hot Tub

3 4
house , Key Largo
This Key Largo oceanfront property, located 1 kilometre from Pigeon Key and 13.5 kilometres from John Pennekamp Coral Reef State Park, offers direct water access.
The 250-square-metre house boasts three bedrooms, three bathrooms, sleeps seventeen guests, and includes a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and an elevator; canoeing is readily available nearby.
Oceanfront 4br Villa | Resort Access + Bunks - Islamorada, FL
Islamorada, FL
10/07 – 15/07
2385 €/nighttotal: 11925 € (5 )

Oceanfront 4br Villa | Resort Access + Bunks

4 6
house , Islamorada, Village of Islands
This Islamorada villa, offering spectacular Atlantic Ocean views, is conveniently located near various attractions in the Village of Islands, though precise distances aren't specified.
The 3100 sq ft (approx. 287 sq m) property boasts four bedrooms, four bathrooms, and sleeps up to ten guests, featuring a full kitchen, swimming pool, Jacuzzi, and two-car garage; oceanfront access allows for immediate enjoyment of waterfront activities.
©2026 cozycozy.com