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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.

114 M² House ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
No reviews

114 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Islamorada, Village of Islands
Marlin House is a bayside canal home in Islamorada's White Marlin Beach neighborhood, located at Mile Marker 74.5, offering direct access to Florida Bay and a short boat ride to the Atlantic Ocean via the Channel 5 Bridge. This 1230 sq ft home features 2 bedrooms, 1 bathroom, accommodates up to 4 guests, and includes a dock for up to a 38ft boat, a private boat ramp, and exclusive access to a sandy beach.

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.

Ocean View Overlooking Marina Ocean Pointe 5305 - Islamorada, FL
9.6 7 reviews

Ocean View Overlooking Marina Ocean Pointe 5305

house, Tavernier
Ocean Pointe 5305, a Key Largo vacation home near the marina, is a 12-minute walk from Harry Harris Park Beach and within 12 miles of Upper Matecumbe Key and 9 miles of Windley Key Fossil Reef Geological State Park.
This 830-square-foot rental boasts two bedrooms, two bathrooms, sleeps seven, and features a private patio, swimming pool, Jacuzzi, and fully equipped kitchen with a dishwasher, microwave, and fridge; free Wi-Fi and cable TV are also included.
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 house in Islamorada, Village of Islands, offers direct access to a secluded private beach and a private dock, providing a true waterfront escape. This family-friendly villa accommodates up to 10 guests with 3 bedrooms and 3 bathrooms, featuring a heated private pool, a gourmet kitchen, high-speed Gigabit WI-FI, and available provisioning and housekeeping services.
Anglers Reef Vacation Rental - Islamorada, FL
9.7 4 reviews

Anglers Reef Vacation Rental

house, Islamorada, Village of Islands
Anglers Reef Vacation Rental is a short walk from Windley Key and Windley Key Fossil Reef Geological State Park, offering easy access to these popular attractions in Islamorada. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 2-bedroom, 1300 square foot house can accommodate up to 6 guests. Amenities include a private pool with garden views, a fully equipped kitchen, free Wi-Fi, a washing machine, and access to a private beach area and water sports facilities.
Pristine Islamorada Pool Home With Ocean View And - Islamorada, FL
10 25 reviews

Pristine Islamorada Pool Home With Ocean View And

house, Islamorada, Village of Islands
This two-bedroom townhouse is located in Islamorada, overlooking the resort-style swimming pool at Angler's Reef Resort Villas & Marina, just three miles south of Alligator Reef and the only living coral barrier reef in the Continental United States. The apartment has excellent user, location, and cleanliness ratings.
The townhouse offers ocean views and can accommodate up to six guests. Amenities include a full kitchen, two spacious decks, a swimming pool, a garden, parking, internet access, and access to kayaks and a nearby beach.

Frequently Asked Questions about villa rentals in Islamorada, FL

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Best Islamorada, FL villas and beach houses with jacuzzi

Ocean Oasis At Ocean Pointe - Islamorada, FL
8.3 2836 reviews

Ocean Oasis At Ocean Pointe

house, Tavernier
Ocean Oasis at Ocean Pointe is located in Tavernier, a short walk from Harry Harris Park Beach and a drive from Pigeon Key. The property has earned high ratings for its location, cleanliness, and overall guest experience.
This vacation rental offers a comfortable and well-equipped space for your stay. Enjoy a range of amenities including a private beach, a pool with a view, a hot tub, and outdoor play equipment for children, all while enjoying free Wi-Fi.
Tranquility On The Top Floor - Ocean Pointe 2404 - Islamorada, FL
No reviews

Tranquility On The Top Floor - Ocean Pointe 2404

house, Tavernier
This top-floor vacation rental, Ocean Pointe 2404, is located in Tavernier, a 13-minute walk from Harry Harris Park Beach and 65 miles from Miami International Airport.
This 750 square feet condo accommodates up to 6 guests with 1 bedroom and 1 bathroom, featuring a fully equipped kitchen, air conditioning, a swimming pool, hot tub, balcony, and garden.
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.
Nauti Hideaway Ocean Pointe 2314 - Islamorada, FL
8.6 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.

Best Islamorada, FL houses with a kitchen

Aqua Lodge Houseboat -"Conch Shell" - Islamorada, FL
9.3 42 reviews

Aqua Lodge Houseboat -"Conch Shell"

boat, Tavernier
The Waterfront Sunset View Aqua Villa At Conch Shell @ Mangrove Resort Llc is located in Tavernier, Florida, just a 15-minute walk from Baker's Cay Resort Beach and Mariners Hospital. This unique houseboat offers a memorable experience on the water with excellent ratings for location, cleanliness, and overall user satisfaction.
The 500-square-foot houseboat features one bathroom and a range of amenities including a swimming pool, spa, garden, terrace, and parking. Guests can enjoy free Wi-Fi in public areas, a smoke-free environment, and easy access to nearby attractions like the Florida Keys Dive Center and Harry Harris Park.
Snorkel Legendary Reefs - Relax Poolside Op 2315 - Islamorada, FL
No reviews

Snorkel Legendary Reefs - Relax Poolside Op 2315

house, Tavernier
This holiday home in Tavernier is a 13-minute walk from Harry Harris Park Beach and 3 miles from Pigeon Key.
This 930 sq ft vacation rental accommodates up to 10 guests with 1 bedroom and 2 bathrooms, featuring a private garden, swimming pool, hot tub, and a fully equipped kitchen.
Charming Cabana-condo In Picturesque Tavernier - Islamorada, FL
No reviews

Charming Cabana-condo In Picturesque Tavernier

house, Tavernier
This Tavernier cabana-condo is located a 13-minute walk from Harry Harris Park Beach and 3 miles from Pigeon Key.
This 930 sq ft vacation rental sleeps 10 guests and features 2 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, spa, and complimentary WiFi.
Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More - Islamorada, FL
10 16 reviews

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More

cottage, Islamorada, Village of Islands
This Islamorada cottage is located in the Matecumbe district, a 3-minute walk from Islamorada Brewery & Distillery and an 11-minute walk to the History of Diving Museum.
This family-friendly vacation rental offers air conditioning, a full kitchen with a microwave and refrigerator, Wi-Fi, a swimming pool, a hot tub, and on-site parking, with kayaks and bicycles available for guest use.

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.

Islamorada Bungalow 3 - Islamorada, FL
9.6 84 reviews

Islamorada Bungalow 3

bungalow, Islamorada, Village of Islands

Search Family Vacation Homes in Islamorada, FL

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

Private Beach & Dock  / Heated Pool / Dolphin Key - Islamorada, FL
10 1 review

Private Beach & Dock / Heated Pool / Dolphin Key

house, Islamorada, Village of Islands
Heated Pool And Tiki Bar - Stunning Peninsula Paradise Retreat - Islamorada, FL
No reviews

Heated Pool And Tiki Bar - Stunning Peninsula Paradise Retreat

house, Islamorada, Village of Islands
House ∙ 6 Bedrooms ∙ 14 Guests - Islamorada, FL
No reviews

House ∙ 6 Bedrooms ∙ 14 Guests

house, Islamorada, Village of Islands
Islamorada Bungalow 4 - Islamorada, FL
9.7 100 reviews

Islamorada Bungalow 4

bungalow, Islamorada, Village of Islands

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.

177 M² House ∙ 3 Bedrooms ∙ 6 Guests - Islamorada, FL
No reviews

177 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Islamorada, Village of Islands
Bennetts Beach Estate - Islamorada, FL
9.0 2 reviews

Bennetts Beach Estate

house, Key Largo
Islamorada Hideaway - Islamorada, FL
No reviews

Islamorada Hideaway

house, Islamorada, Village of Islands
House ∙ 4 Bedrooms ∙ 12 Guests - Islamorada, FL
9.3 3 reviews

House ∙ 4 Bedrooms ∙ 12 Guests

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.

Pristine Islamorada Pool Home With Ocean View And - Islamorada, FL
10 25 reviews

Pristine Islamorada Pool Home With Ocean View And

house, Islamorada, Village of Islands

Best Islamorada, FL houses with air conditioning

The Lighthouse | Ocean + Pool Views, Gameroom - Islamorada, FL
10 2 reviews

The Lighthouse | Ocean + Pool Views, Gameroom

house, Islamorada, Village of Islands
Isla Honeydew: 3 En-suite Bedrooms, Pool, Dock - Islamorada, FL
10 9 reviews

Isla Honeydew: 3 En-suite Bedrooms, Pool, Dock

house, Islamorada, Village of Islands
Charming 2br Cottage In Prime Keys Location W/pool - Islamorada, FL
9.9 147 reviews

Charming 2br Cottage In Prime Keys Location W/pool

cottage, 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
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