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Islamorada, FL villas
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528 Villa rentals in Islamorada, FL

Browse Waterfront Vacation Homes in Islamorada, FL

Unwind at these welcoming coastal vacation homes in Islamorada, FL, ideally located for exploring regional beach-town boardwalks.

Flamingo Flats Ocean Pointe 5306 - Islamorada, FL
9.8 6 reviews

Flamingo Flats Ocean Pointe 5306

house, Tavernier
Flamingo Flats Ocean Pointe 5306, a Key Largo vacation home, is a short drive from Harry Harris Park Beach and 2.8 miles from Pigeon Key.
This 830-square-foot rental boasts two bedrooms, two bathrooms, accommodates six guests, and includes a private patio with ocean views, a pool, a fully equipped kitchen, Wi-Fi, cable TV, and a washer.

Find the Best Holiday Houses with Swimming Pool in Islamorada, FL

A vacation home with a pool near the water in Islamorada, FL is the perfect base to complement your adventures.

Oceanside Anglers Reef Home With Beach Pool And Kayaks - Islamorada, FL
No reviews

Oceanside Anglers Reef Home With Beach Pool And Kayaks

house, Islamorada, Village of Islands
This oceanfront house is located in Islamorada, Village of Islands, 71 miles from Miami International Airport.
This 1300 square foot residence accommodates up to 9 guests with 2 bedrooms and 3 bathrooms, featuring a beach pool, complimentary kayaks, a waterpark, and free WiFi and parking.
Nauti Hideaway Ocean Pointe 2314 - Islamorada, FL
8.7 13 reviews

Nauti Hideaway Ocean Pointe 2314

house, Tavernier
Nauti Hideaway Ocean Pointe 2314, located in Key Largo, offers a 2-bedroom, 2-bathroom house near Harry Harris Park Beach, with easy access to Pigeon Key, Windley Key, and John Pennekamp Coral Reef State Park.
This 830-square-foot vacation rental boasts a private pool, Jacuzzi, and patio with ocean views, accommodating up to 7 guests and including amenities such as a fully equipped kitchen, free Wi-Fi, and a washer/dryer.
Isla Mirabelle: Boutique Resort, Free Boat Dockage Sep-oct Only! - Islamorada, FL
10 8 reviews

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

house, Islamorada, Village of Islands
Isla Mirabelle, a three-bedroom waterfront villa in Islamorada's Matecumbe district, is a 10-minute walk from the Islamorada Brewery & Distillery and Keys History & Discovery Center, and within 15 minutes of the History of Diving Museum.
This 1680-square-foot smoke-free property sleeps six, boasting a fully equipped kitchen, private balcony, heated pool, dock, and barbecue grills, all within walking distance of local attractions.
Bliss On The Beach! - Islamorada, FL
No reviews

Bliss On The Beach!

house, Islamorada, Village of Islands
This Islamorada rental home is located in a private, gated community within the Village of Islands, offering direct water access and beautiful sunset views.
This 2-bedroom, 2-bathroom villa accommodates up to 4 guests and features air conditioning, internet, a kitchen, a swimming pool, and parking, with a minimum 28-day stay required for enjoying fishing off the dock and the newly renovated community pool and clubhouse.

Frequently Asked Questions about villa rentals in Islamorada, FL

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Best Islamorada, FL villas and beach houses with jacuzzi

Front Beach | Paradise Villa | Islamorada Fl Keys - Islamorada, FL
No reviews

Front Beach | Paradise Villa | Islamorada Fl Keys

house, Islamorada, Village of Islands
This oceanfront estate in Islamorada, Village of Islands, offers direct access to a private beach on a sprawling private property.
This luxury villa accommodates 14 guests with 7 bedrooms and 8 bathrooms, featuring a swimming pool, jacuzzi, private beach, children's play area, and on-site beauty salon, with comprehensive concierge services available.
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,sups - Islamorada, FL
10 178 reviews

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,sups

bungalow, 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.
Keys Waterfront Condo Pool Beach And Views - Islamorada, FL
No reviews

Keys Waterfront Condo Pool Beach And Views

house, Tavernier
This house in Tavernier is a 13-minute walk to Harry Harris Park Beach and 3 miles from Pigeon Key.
This 930 square foot vacation rental features 2 bedrooms, 2 bathrooms, a private pool, hot tub, garden, and accommodates up to 10 guests with air conditioning, a full kitchen, and WiFi.
Key Largo Captains Quarters Ocean Pointe 4405 - Islamorada, FL
8.8 6 reviews

Key Largo Captains Quarters Ocean Pointe 4405

house, Tavernier
Ocean Pointe 4405 in Key Largo, a short drive from Pigeon Key, Windley Key, and John Pennekamp Coral Reef State Park, offers easy access to Harry Harris Park Beach (a 12-minute walk).
This 830-square-foot house features two bedrooms, two bathrooms, accommodates seven guests, and includes a private patio with ocean views, a swimming pool, a Jacuzzi, and a fully equipped kitchen.

Best Islamorada, FL houses with a kitchen

62 M² Villa ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
10 14 reviews

62 M² Villa ∙ 2 Bedrooms ∙ 4 Guests

house, Islamorada, Village of Islands
This Islamorada villa offers direct Florida Bay water views from a private 1-acre lot, located within walking distance of shops, bars, cafes, and restaurants, including the Islamorada Brewery & Distillery.
This 670 sq ft villa accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, free Wi-Fi, and a 1200 sq ft rooftop terrace with grill and seating, plus a marina with a boat launch ramp.
New - Luxury Seascape W/pool+free Dockage+gameroom - Islamorada, FL
9.9 33 reviews

New - Luxury Seascape W/pool+free Dockage+gameroom

house, Islamorada, Village of Islands
This Islamorada vacation home, located in the gated Peaceful Palms community, offers direct ocean access with private dockage for boats up to 26 feet, a mile from Publix and walking distance to Robbie's Marina and other attractions.
The three-bedroom, three-bathroom house sleeps eight guests and boasts a fully stocked kitchen, two oceanfront balconies, a private lower-level entertainment area with games and workout equipment, kayaks, paddleboards, and access to a community heated pool.
Modern And Coastal 3212 Is Across From Pool - Islamorada, FL
9.0 3 reviews

Modern And Coastal 3212 Is Across From Pool

house, Tavernier
This Key Largo vacation rental is a short walk from Harry Harris Park Beach and a short drive from attractions like Pigeon Key and John Pennekamp Coral Reef State Park.
The 900-square-foot house features two bedrooms, two bathrooms, a fully equipped kitchen, a private patio with sea views, a swimming pool, a jacuzzi, and accommodates up to eight guests.
Aqua Lodge Houseboat "Sand Dollar" - Islamorada, FL
9.5 64 reviews

Aqua Lodge Houseboat "Sand Dollar"

apartment, Tavernier
The Sand Dollar houseboat is located in the Mangrove Marina Resorts in Tavernier, Florida, offering easy access to the Florida Keys' beautiful waters. It has received excellent ratings for its location, cleanliness, and overall user experience.
The houseboat features a master bedroom with a queen-sized bed, a loft with two twin beds, a queen-sized sleeper sofa in the living room, a full bathroom with a stand-up shower, and a full kitchen with a 4-burner stove. Guests can enjoy amenities like a swimming pool, Tiki huts, BBQ area, and access to various water activities, including fishing, snorkeling, diving, kayaking, and boating.

Our Favorite Luxury Vacation Homes in Islamorada, FL

These upscale vacation homes in Islamorada, FL provide the perfect blend of premium amenities and a highly desirable prime location.

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

Oceanside Family Condo With Pool And Beach Access

house, Tavernier

Search Family Vacation Homes in Islamorada, FL

Family-friendly vacation homes in Islamorada, FL offer the space needed to spread out.

404 M² House ∙ 4 Bedrooms ∙ 9 Guests - Islamorada, FL
No reviews

404 M² House ∙ 4 Bedrooms ∙ 9 Guests

house, Islamorada, Village of Islands
Isla Key Acaí: Waterfront Boutique Resort, Free Boat Dockage Sep-oct Only! - Islamorada, FL
9.8 9 reviews

Isla Key Acaí: Waterfront Boutique Resort, Free Boat Dockage Sep-oct Only!

house, Islamorada, Village of Islands
Mirage | Islamorada Oceanfront Community, 3br, Near Sandbar, Pool - Islamorada, FL
7.0 2 reviews

Mirage | Islamorada Oceanfront Community, 3br, Near Sandbar, Pool

house, Islamorada, Village of Islands
Ocean Pointe 2309 - Islamorada, FL
8.9 10 reviews

Ocean Pointe 2309

house, Tavernier

Check Out Dog-Friendly Holiday Houses in Islamorada, FL

No need to leave your dog behind. These vacation homes in Islamorada, FL offer dog-friendly amenities for a stress-free pet stay.

Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location - Islamorada, FL
10 1 review

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

house, Islamorada, Village of Islands
At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom - Islamorada, FL
8.0 1 review

At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

house, Islamorada, Village of Islands
Brand New Oceanside Paradise Waterfront With Pool And Hot Tub - Islamorada, FL
10 1 review

Brand New Oceanside Paradise Waterfront With Pool And Hot Tub

house, Key Largo
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

Explore Holiday Houses with Wellness in Islamorada, FL

Wellness travel to Islamorada, FL starts with a vacation home that features a professional spa. Find your perfect restorative retreat here.

The Nest Villa & Marina In The Heart Of Islamorada - Islamorada, FL
9.8 18 reviews

The Nest Villa & Marina In The Heart Of Islamorada

house, Islamorada, Village of Islands

Best Islamorada, FL houses with air conditioning

Mirage - Islamorada Oceanfront Community, 3br, Near Sandbar, Pool - Islamorada, FL
No reviews

Mirage - Islamorada Oceanfront Community, 3br, Near Sandbar, Pool

house, Islamorada, Village of Islands
Lyons Landing - Islamorada, FL
No reviews

Lyons Landing

house, Islamorada, Village of Islands
Bright Sunny Suite With Magnificent Ocean Views - Islamorada, FL
No reviews

Bright Sunny Suite With Magnificent Ocean Views

house, Tavernier
Hidden Gem Duplex In Heart Of Islamorada Sleeps 8 - Islamorada, FL
No reviews

Hidden Gem Duplex In Heart Of Islamorada Sleeps 8

house, Islamorada, Village of Islands
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