Search Islamorada, FL villas and holiday homes

528 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Islamorada, FL villas
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

528 Villa rentals in Islamorada, FL

Seashore Holiday Homes in Islamorada, FL, United States

Open your glass doors and step directly from your living room onto the soft sand at houses on the seashore in Islamorada, FL, United States.

Private Beach Private Overwater Dock Heated Pool Mahi Key - Islamorada, FL
No reviews

Private Beach Private Overwater Dock Heated Pool Mahi Key

house, Islamorada, Village of Islands
This Islamorada holiday home is situated 2.3 kilometres from Sea Oats Beach, with Upper Matecumbe Key (9.2 km), Theatre of the Sea (13.4 km), and Windley Key (14.2 km) also nearby.
This three-bedroom, three-bathroom property boasts 123 square metres of living space, accommodating up to 10 guests and featuring a private overwater dock, heated pool, and fully equipped kitchen; cable TV and air conditioning are also included.

Holiday Homes and Beach Houses with a Pool in Islamorada, FL, United States

Swim laps in total seclusion surrounded by swaying palm trees at beach houses with a private pool in Islamorada, FL, United States.

Key Largo Baha Penthouse Ocean Pointe 1416 - Islamorada, FL
9.6 8 reviews

Key Largo Baha Penthouse Ocean Pointe 1416

house, Tavernier
Key Largo Baha Penthouse Ocean Pointe 1416, situated in Key Largo, Florida, offers a 77 square metre, two-bedroom, two-bathroom apartment approximately 1.6km from Harry Harris Park Beach and conveniently located for exploring Pigeon Key, Windley Key, and John Pennekamp Coral Reef State Park.
This self-catering property sleeps seven guests and boasts a fully equipped kitchen, private patio with ocean views, swimming pool, jacuzzi, free Wi-Fi, and access to a washing machine.
Private Beach / Heated Pool / Volleyball Court/ Orchid Beach Key - Islamorada, FL
No reviews

Private Beach / Heated Pool / Volleyball Court/ Orchid Beach Key

house, Islamorada, Village of Islands
This private beachfront villa in Islamorada's Matecumbe neighbourhood offers direct ocean views and is a short drive to the Keys History & Discovery Center and History of Diving Museum, with Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park nearby.
Spanning 418 square meters, this expansive property accommodates up to 12 guests across a central villa, a primary suite villa, and a guest suite wing, featuring a heated infinity pool, hot tub, a 100-meter ocean dock, and on-site water sports like kayaking and paddleboarding.
Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable - Islamorada, FL
10 2 reviews

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

house, Islamorada, Village of Islands
Isla Mirabelle, a waterfront holiday home in Islamorada, Village of Islands, offers private dock access and is a short walk from Upper Matecumbe Key, with Windley Key 4.3km and John Pennekamp Coral Reef State Park 34km away.
This three-bedroom, three-bathroom property boasts 156 square metres of living space, a heated swimming pool, fitness centre, free Wi-Fi, and parking, comfortably accommodating up to nine guests.
Coastal Retreat With Private Balcony, Pool, & Easy Beach Access - Islamorada, FL
8.2 56 reviews

Coastal Retreat With Private Balcony, Pool, & Easy Beach Access

house, Tavernier
Ocean Point #2210 is located in Tavernier, Florida, just 5 kilometres from Harry Harris Park Beach and within easy reach of attractions like Pigeon Key (5 kilometres) and Windley Key (13 kilometres). The property has received very good ratings for its location and overall experience, as well as a good rating for cleanliness.
This two-bedroom apartment, spanning 77 square metres, comfortably accommodates up to four guests. Ocean Point #2210 offers a range of amenities including air conditioning, a swimming pool, a tennis court, a terrace, free Wi-Fi, and parking, plus a fully equipped kitchen for those who prefer to cook their own meals.

Frequently asked questions about villa rentals in Islamorada, FL

Popular destinations

Best Islamorada, FL villas and holiday homes with a kitchen

Isla Key Lime: Boutique Resort, Free Boat Dockage Sept-oct Only! - Islamorada, FL
10 8 reviews

Isla Key Lime: Boutique Resort, Free Boat Dockage Sept-oct Only!

house, Islamorada, Village of Islands
Isla Key Lime: Waterfront Boutique Resort, a three-bedroom villa in Matecumbe, Islamorada, is located within 1.6km of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and under 2.4km from the History of Diving Museum.
This smoke-free property boasts 156 square metres of living space, sleeping up to six guests and featuring a fully equipped kitchen, private balcony, access to a garden, and free Wi-Fi; outdoor barbecues are also available.
Retro Reef House 5406 Designer Marina View - Islamorada, FL
No reviews

Retro Reef House 5406 Designer Marina View

house, Tavernier
This holiday cottage in Tavernier offers a spacious retreat, situated a 13-minute walk from Harry Harris Park Beach and within easy reach of attractions such as Pigeon Key (4.8 kilometres) and Windley Key (13 kilometres).
This property boasts 78 square metres of living space, accommodating up to 8 guests with 2 bedrooms and 2 bathrooms, and features modern amenities including free WiFi, air conditioning, a hot tub, a full kitchen with a dishwasher and microwave, a balcony, patio, and barbecue.
Salty Mermaid Ocean Pointe 4406 - Islamorada, FL
9.5 4 reviews

Salty Mermaid Ocean Pointe 4406

house, Tavernier
Salty Mermaid Ocean Pointe 4406, a two-bedroom house in Tavernier, Florida, is a short 1.9km walk from Harry Harris Park Beach and within a few miles of Pigeon Key, Windley Key, and John Pennekamp Coral Reef State Park.
This 80 square metre property boasts a private patio with ocean views, a shared swimming pool, jacuzzi, and accommodates up to eight guests with amenities including a fully equipped kitchen, free Wi-Fi, and a washing machine.
Oceanfront Islamorada Townhome With Pool & Dock - Islamorada, FL
10 8 reviews

Oceanfront Islamorada Townhome With Pool & Dock

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.

Best Islamorada, FL villas and holiday homes with air conditioning

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.
Sea Glass & Sunshine 2207 Ocean Pointe - Islamorada, FL
No reviews

Sea Glass & Sunshine 2207 Ocean Pointe

house, Tavernier
This two-bedroom, two-bathroom holiday home in Tavernier is situated a 13-minute walk from Harry Harris Park Beach and 4.8 kilometres from Pigeon Key.
This 78-square-metre property offers a swimming pool, hot tub, air conditioning, a fully equipped kitchen, and parking for up to 7 guests.
Anglers Reef Home  Pool  Kayaks  Paddle Boards - Islamorada, FL
9.8 24 reviews

Anglers Reef Home Pool Kayaks Paddle Boards

house, Islamorada, Village of Islands
This charming house is located in the Angler's Reef complex at Mile Marker 85 in Islamorada, a short drive from the popular attractions of the Upper Keys. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The property offers two bedrooms and two bathrooms, comfortably accommodating up to six guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private pool, direct beach access, and kayaking opportunities.
Sea View And Sunrise Top Floor Ocean Pointe 2412 - Islamorada, FL
9.7 13 reviews

Sea View And Sunrise Top Floor Ocean Pointe 2412

house, Tavernier
Ocean Pointe 2412 in Key Largo, Florida, offers a top-floor apartment with direct sea views, a 15-minute walk (approx. 2.4km) from Harry Harris Park Beach and 18km from Upper Matecumbe Key and Windley Key.
This 77 square metre property sleeps six guests and boasts two bedrooms, two bathrooms, a fully equipped kitchen, private patio, swimming pool access, Jacuzzi, and free Wi-Fi; laundry facilities are also available.

Holiday Homes with a Hot Tub in Islamorada, FL, United States

Watch the ocean stars from the bubbling warmth of a private shoreline hot tub at beach houses in Islamorada, FL, United States.

Saltair Loft Ocean Pointe 2 Br 2 Ba 1411 - Islamorada, FL
10 2 reviews

Saltair Loft Ocean Pointe 2 Br 2 Ba 1411

house, Tavernier
Ocean View Corner Penthouse Ocean Pointe 5416 - Islamorada, FL
9.6 16 reviews

Ocean View Corner Penthouse Ocean Pointe 5416

house, Tavernier
Sunrise Penthouse 3316 Ocean Pointe 1br 2ba - Islamorada, FL
10 1 review

Sunrise Penthouse 3316 Ocean Pointe 1br 2ba

house, Tavernier
2306 Ocean Pointe Suites - Islamorada, FL
No reviews

2306 Ocean Pointe Suites

house, Tavernier

View Exclusive Luxury Houses in Islamorada, FL, United States

Bask in private tropical exclusivity with premier shoreline architecture and absolute privacy at luxury houses by the sea in Islamorada, FL, United States.

Family Keys Escape: Speakeasy·dock·pool·bbq Patio - Islamorada, FL
10 14 reviews

Family Keys Escape: Speakeasy·dock·pool·bbq Patio

house, Islamorada, Village of Islands

Find the Best Family Houses in Islamorada, FL, United States

Give the family an unforgettable seaside holiday with a massive kitchen and direct sand access at family beach houses in Islamorada, FL, United States.

Anglers Reef Paradise - Islamorada, FL
8.6 27 reviews

Anglers Reef Paradise

house, Islamorada, Village of Islands
Ocean Oasis At Ocean Pointe - Islamorada, FL
8.3 2933 reviews

Ocean Oasis At Ocean Pointe

house, Tavernier
Cottage ∙ 1 Bedroom ∙ 4 Guests - Islamorada, FL
No reviews

Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage, Islamorada, Village of Islands
Isla Guava: Boutique Resort, Free Boat Dockage Sept-oct Only! - Islamorada, FL
9.2 5 reviews

Isla Guava: Boutique Resort, Free Boat Dockage Sept-oct Only!

house, Islamorada, Village of Islands

Best Islamorada, FL villas and holiday homes with parking

Oceanfront Private Cottage! - Islamorada, FL
10 117 reviews

Oceanfront Private Cottage!

cottage, Islamorada, Village of Islands
Modern And Coastal Ocean Pointe 2307 - Islamorada, FL
9.4 11 reviews

Modern And Coastal Ocean Pointe 2307

house, Tavernier
139 M² House ∙ 3 Bedrooms ∙ 8 Guests - Islamorada, FL
No reviews

139 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Islamorada, Village of Islands
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location - Islamorada, FL
No reviews

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

house, Islamorada, Village of Islands

Top-Rated Holiday Homes with Free Breakfast in Islamorada, FL, United States

Find beach houses with free breakfast in Islamorada, FL, United States and start each morning with ease.

Key Lime Cottage In The Heart Of Islamorada - Islamorada, FL
10 5 reviews

Key Lime Cottage In The Heart Of Islamorada

house, Islamorada, Village of Islands
©2026 cozycozy.com