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Villas in Islamorada

Find the villas that appeal to you the most

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The 10 Best Villas in Islamorada, USA

Check out our pick of great villas in Islamorada

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Anglers Reef Getaway, villa in Islamorada

Guests at the villa will be able to enjoy activities in and around Islamorada, like fishing. Snorkelling and cycling can be enjoyed nearby, while a bicycle rental service and a private beach area are also available on-site.

loved the location and the quick responses from the host.

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9
Superb
24 reviews
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Anglers Reef Paradise, villa in Islamorada

Anglers Reef Paradise is located in Islamorada, 300 metres from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

This air-conditioned holiday home has 2 bedrooms and 2.5 bathrooms, a cable flat-screen TV, and a fully equipped kitchen. The holiday home also provides a bathroom with a shower.

Location & the grounds & pool were amazing.

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9.2
Superb
25 reviews
Price from
€ 371
per night
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Isla Tamarillo - Waterfront Boutique Resort, Island Paradise, Prime Location, villa in Islamorada

With free WiFi, this 3-bedroom holiday home offers a TV, a washing machine and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking.

John Pennekamp State Park is 33 km from the holiday home, while Florida Keys Aquarium Encounters is 47 km from the property. The nearest airport is Miami International Airport, 119 km from Isla Tamarillo - Waterfront Boutique Resort, Island Paradise, Prime Location.

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Price from
€ 771
per night
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Isla Mirabelle - Waterfront Boutique Resort, Island Paradise, Prime Location, villa in Islamorada

With free WiFi, this 3-bedroom holiday home offers a TV, a washing machine and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking.

John Pennekamp State Park is 33 km from the holiday home, while Florida Keys Aquarium Encounters is 47 km from the property. The nearest airport is Miami International Airport, 119 km from Isla Mirabelle - Waterfront Boutique Resort, Island Paradise, Prime Location.

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Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location, villa in Islamorada

The spacious villa is equipped with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The accommodation is non-smoking.

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Price from
€ 566
per night
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Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location, villa in Islamorada

The spacious villa is fitted with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The accommodation is non-smoking.

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Price from
€ 531
per night
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Isla Key Lime - Island Paradise, Waterfront Pool, Prime Location, villa in Islamorada

The spacious villa is equipped with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The accommodation is non-smoking.

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Price from
€ 681
per night
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Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location, villa in Islamorada

The spacious villa has 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The accommodation is non-smoking.

History of Diving Museum is 1 km from the villa, while Windley Key Fossil Reef Geological State Park is 3.2 km from the property. The nearest airport is Miami International Airport, 119 km from Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location.

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Price from
€ 361
per night
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Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location, villa in Islamorada

The spacious villa is fitted with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The accommodation is non-smoking.

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Price from
€ 662
per night
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Peaceful Palms A2, villa in Islamorada

The recently renovated holiday home has 3 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The accommodation is non-smoking.

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Price from
€ 374
per night
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All villas in Islamorada

Looking for a villa?

Perfect for families, groups or couples who enjoy luxury and independence while travelling. Enjoy the space and privacy of these fully-furnished, self-standing mansions — travellers can cook, lounge and explore at their leisure. Note that in Bali, a resort will also be called a villa.
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Most booked villas in Islamorada this month

Enjoy breakfast in Islamorada!

Great access to the city centre! Check these villas in Islamorada

  • EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2 reviews

    Situated in Islamorada and only 3.8 km from Windley Key, EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS features accommodation with sea views, free WiFi and free private parking.

  • Isla Tamarillo - Waterfront Boutique Resort, Island Paradise, Prime Location

    Boasting air-conditioned accommodation with a balcony, Isla Tamarillo - Waterfront Boutique Resort, Island Paradise, Prime Location is set in Islamorada.

  • Isla Mirabelle - Waterfront Boutique Resort, Island Paradise, Prime Location

    Boasting air-conditioned accommodation with a balcony, Isla Mirabelle - Waterfront Boutique Resort, Island Paradise, Prime Location is set in Islamorada.

  • Little Bay Cottage

    Situated in Islamorada, 1.1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Little Bay Cottage offers air conditioning.

  • Little Bay Compound

    Boasting sea views, Little Bay Compound features accommodation with a garden and a balcony, around 1.1 km from Upper Matecumbe Key. This beachfront property offers access to a terrace and free WiFi.

  • Martin Family Fish Camp

    Martin Family Fish Camp is set in Islamorada, 4.9 km from Windley Key, 21 km from Pigeon Key, as well as 34 km from John Pennekamp State Park.

  • The Oasis
    Central location

    Boasting air-conditioned accommodation with a private pool, sea view and a balcony, The Oasis is set in Islamorada. This beachfront property offers access to a terrace and free private parking.

  • 3 Lux Ensuites Walk Boat Island

    Featuring air-conditioned accommodation with a patio, 3 Lux Ensuites Walk Boat Island is located in Islamorada.

  • Beacon Reef 503

    Boasting sea views, Beacon Reef 503 offers accommodation with a garden and a balcony, around 2.4 km from Upper Matecumbe Key.

  • Beacon Reef 501

    Offering a garden and sea view, Beacon Reef 501 is situated in Islamorada, 2.4 km from Upper Matecumbe Key and 3.1 km from Windley Key. This beachfront property offers access to a balcony.

  • Beacon Reef 406

    Boasting sea views, Beacon Reef 406 features accommodation with a garden and a balcony, around 2.4 km from Upper Matecumbe Key.

  • Beacon Reef 310

    Boasting sea views, Beacon Reef 310 features accommodation with a garden and a balcony, around 2.4 km from Upper Matecumbe Key.

  • Beacon Reef 307

    Boasting sea views, Beacon Reef 307 features accommodation with a garden and a balcony, around 2.4 km from Upper Matecumbe Key.

  • Beacon Reef 306

    Featuring sea views, Beacon Reef 306 provides accommodation with a garden and a balcony, around 2.4 km from Upper Matecumbe Key.

  • Beacon Reef 301

    Boasting sea views, Beacon Reef 301 features accommodation with a garden and a terrace, around 2.4 km from Upper Matecumbe Key.

  • Beacon Reef 222

    Featuring sea views, Beacon Reef 222 offers accommodation with a garden and a terrace, around 2.4 km from Upper Matecumbe Key.

  • Sunshine Place
    Central location

    Sunshine Place is a beachfront property set in Islamorada, 1.4 km from Windley Key and 4.2 km from Upper Matecumbe Key.

  • Palms 417
    Central location

    Featuring sea views, Palms 417 offers accommodation with a balcony, around 3.3 km from Upper Matecumbe Key. This beachfront property offers access to a terrace.

  • Palms 407
    Central location

    Palms 407 is a beachfront property located in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key.

  • Palms 404
    Central location

    Palms 404 is a beachfront property situated in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key.

  • Palms 317
    Central location

    Palms 317 is a beachfront property located in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key.

  • Palms 314
    Central location

    Palms 314 is a beachfront property situated in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key.

  • Palms 313
    Central location

    Palms 313 is a beachfront property located in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key.

  • Palms 301
    Central location

    Palms 301 is a beachfront property set in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key.

  • Palms 309
    Central location

    Palms 309 is a beachfront property set in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key.

  • Anglers Reef Vacation Rental

    Boasting air-conditioned accommodation with a private pool, garden view and a balcony, Anglers Reef Vacation Rental is set in Islamorada.

  • Lyons Landing
    Central location

    Lyons Landing is located in Islamorada, 7.8 km from Upper Matecumbe Key, 16 km from Pigeon Key, and 28 km from John Pennekamp State Park.

  • Harbor House
    Central location

    Harbor House is set in Islamorada, 7.5 km from Upper Matecumbe Key, 15 km from Pigeon Key, and 28 km from John Pennekamp State Park.

Travelling by car? These villas in Islamorada offer free parking!

  • West Plaza Del Lago

    Located 2.2 km from Anne's Beach, 13 km from Upper Matecumbe Key and 18 km from Windley Key, West Plaza Del Lago offers accommodation situated in Islamorada.

  • Villa Riolo

    Villa Riolo is situated in Islamorada, 9.2 km from Upper Matecumbe Key, 14 km from Windley Key, and 30 km from Pigeon Key.

  • Sandglass 4

    Boasting a spa bath, Sandglass 4 is set in Islamorada. Among the facilities at this property are a 24-hour front desk and an ATM, along with free WiFi throughout the property.

  • Pelican Landing

    Offering sea views, Pelican Landing is an accommodation situated in Islamorada, 1.1 km from Sea Oats Beach and 2.2 km from Anne's Beach.

  • Ocean Harbour K31

    Ocean Harbour K31 is a beachfront property set in Islamorada, 4.4 km from Windley Key and 10 km from Upper Matecumbe Key.

  • Blue Water Retreat

    Featuring air-conditioned accommodation with a private pool, sea view and a balcony, Blue Water Retreat is set in Islamorada.

  • Antigua Place

    Situated 2.3 km from Anne's Beach, 13 km from Upper Matecumbe Key and 18 km from Windley Key, Antigua Place provides accommodation set in Islamorada.

  • Unity & Autonomy 2 sides a Beach Duplex & 70' DOCK

    Featuring air-conditioned accommodation with a patio, Unity & Autonomy 2 sides a Beach Duplex & 70' DOCK is located in Islamorada.

Villas that guests love in Islamorada

  • Chesapeake Beach Resort

    Chesapeake Beach Resort

    Villa in Islamorada
    Avg. price/night: € 281.15
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 821 reviews
    The layout and I like that’s acomplete boutique hotel unique great staff and absolutely great planned villas n rooms
    ventura
    Family with young children
  • Hadley Resort and Marina

    Hadley Resort and Marina

    Villa in Islamorada
    Avg. price/night: € 224.90
    7.0
    Scored 7.0
    Good
    Rated good
     · 1,232 reviews
    Our 2 storey pool villa was fabulous. Really liked the pool area and breakfast was nice in the lobby.
    Sarah
    Young couple
  • Chesapeake Beach Resort

    Chesapeake Beach Resort

    Villa in Islamorada
    Avg. price/night: € 281.15
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 821 reviews
    Upgraded to a villa! Beautiful spot to watch sunrise. Hot tub and two pools were lovely. Champagne complimentary on arrival. Very good restaurant next door. Good variety of foods at breakfast which you could eat at outdoor tables or take to your room. Villa very clean with a well equipped kitchen. All staff we encountered were very pleasant!
    Mason
    Young couple
  • Islander Bayside Villas & Boatslips

    Islander Bayside Villas & Boatslips

    Villa in Islamorada
    Avg. price/night: € 384.82
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 250 reviews
    The villas are so confortable and have all the amenities that we need
    Martina
    Group
  • Islander Bayside Villas & Boatslips

    Islander Bayside Villas & Boatslips

    Villa in Islamorada
    Avg. price/night: € 384.82
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 250 reviews
    The villas are nice enough, clean and comfortable. The pool area is absolutely phenomenal, particularly at sunset.
    A
    Anonymous
    Family with young children
  • Islander Bayside Villas & Boatslips

    Islander Bayside Villas & Boatslips

    Villa in Islamorada
    Avg. price/night: € 384.82
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 250 reviews
    The best thing about this villa was the ability to use the Islander Resort for a fraction of the price. I was a little disappointed in the quality of the Villa although it was cheaper than its sister property it was still pricey. The outside of the villas are beautiful but they definitely could use some updated paint and carpeting inside. If you are looking for value in comparison to the Islander then this is the perfect spot. Overall I still really enjoyed the stay. Very close to restaurants.
    Sarah
    Family with young children
  • Pines & Palms Resort

    Pines & Palms Resort

    Villa in Islamorada
    Avg. price/night: € 338.63
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 848 reviews
    The villas were very comfortable and clean, the grounds were well kept and the property is excellent for a quite and peaceful vacation!
    Daniel
    Young couple
  • Postcard Inn Beach Resort & Marina

    Postcard Inn Beach Resort & Marina

    Villa in Islamorada
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 1,217 reviews
    Beachfront, on the water. Lots of activities and food options.
    Celeste
    Young couple
  • Angler's Reef Resort

    Angler's Reef Resort

    Villa in Islamorada
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 7 reviews
    I loved the fact that we could all be together on vacation, but have our own separate villas. Each villa (#103 & 116) was beautiful, well appointed and immaculate. 116 had a big yard with fire pit, deck, lawn furniture, picnic table and a corn hole set which was perfect for family get togethers.
    Sara
    Family with young children
  • Dream Escape at Anglers Reef Islamorada

    Dream Escape at Anglers Reef Islamorada

    Villa in Islamorada
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 8 reviews
    This was our first time using booking.com and staying at Anglers Reef. Both were a success. I highly recommend Anglers Reef for a family friendly experience in paradise. The villa accomodations were wonderful and the host was very responsive to our questions. The pool, views of the water, beautiful palm trees, fishing/dock area, and cute villas exceeded our expectations. Also, it was a great location in the Keys for finding outdoor fun and great restaurants.
    Anthony
    Family with young children

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