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The 10 Best Villas in Islamorada, USA

Check out our selection of great villas in Islamorada

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Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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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
Wonderful
24 reviews

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.

It was very clean and confortable; and the facilities where great, we enjoyed our time at the beach and used the canoes and paddle board! Great time

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9.2
Wonderful
26 reviews

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
$342.17
per night

The holiday home is fitted with 2 separate bedrooms and includes a fully equipped kitchen with a dishwasher, oven and dining area.

Pigeon Key is 34 km from the holiday home, while Florida Keys Aquarium Encounters is 35 km away. The nearest airport is Key West International Airport, 116 km from West Plaza Del Lago.

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Villa Riolo is situated in Islamorada, 9.2 km from Upper Matecumbe Key, 14 km from Windley Key, and 30 km from Pigeon Key. Both free WiFi and parking on-site are available at the holiday home free of charge. The property is non-smoking and is located 2.5 km from Sea Oats Beach.

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Price from
$252.22
per night

Sunshine Place is a beachfront property set in Islamorada, 1.4 km from Windley Key and 4.2 km from Upper Matecumbe Key. Among the facilities at this property are a 24-hour front desk and an ATM, along with free WiFi throughout the property. The property is non-smoking and is situated 17 km from Pigeon Key.

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The spacious holiday home is fitted with 5 separate bedrooms and includes a fully equipped kitchen with a dishwasher, oven and dining area.

Anne's Beach is 2.3 km from the holiday home, while Upper Matecumbe Key is 11 km from the property. The nearest airport is Key West International Airport, 116 km from Sandglass 4.

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Price from
$640.15
per night

The spacious holiday home features 4 separate bedrooms and includes a fully equipped kitchen with a dishwasher, oven and dining area.

Windley Key is 18 km from the holiday home, while Pigeon Key is 34 km from the property. The nearest airport is Key West International Airport, 116 km from Pelican Landing.

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Price from
$549.25
per night

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. The holiday home features parking on-site, a fitness room and a 24-hour front desk.

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Palms 407 is a beachfront property located in Islamorada, 3.3 km from Upper Matecumbe Key and 8.3 km from Windley Key. Among the facilities at this property are a 24-hour front desk and a lift, along with free WiFi throughout the property. The property is non-smoking and is set 24 km from Pigeon Key.

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Looking for a villa?

Perfect for families, groups, or couples who enjoy luxury and independence while traveling. Enjoy the space and privacy of these fully-furnished, free-standing mansions – travelers can cook, lounge, and explore at their own pace. Note that in Bali, a resort will also be called a villa.
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  • Anglers Reef Getaway
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 24 reviews

    Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

    The amenities,the location, the villas and the pool

  • Anglers Reef Paradise
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 26 reviews

    Anglers Reef Paradise is located in Islamorada, 984 feet from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

    perfektes Südstaatenfeeling sehr exquisit und sicher

  • Peaceful Palms A2

    Peaceful Palms A2 is a recently renovated vacation home in Islamorada, near Windley Key. This vacation home features air-conditioned accommodations with a terrace.

  • West Plaza Del Lago

    West Plaza Del Lago offers accommodations in Islamorada, a 12-minute walk from Sea Oats Beach and 1.3 miles from Anne's Beach.

  • Villa Riolo
    Breakfast options

    Villa Riolo is located in Islamorada, just 1.6 miles from Sea Oats Beach and 5.7 miles from Upper Matecumbe Key. Both free Wifi and parking on-site are available at the vacation home free of charge.

  • Sunshine Place
    Breakfast options

    Sunshine Place offers accommodations in Islamorada, a 17-minute walk from Windley Key and 2.6 miles from Upper Matecumbe Key.

  • Sandglass 4
    Breakfast options

    Sandglass 4 is located in Islamorada, just a few steps from Sea Oats Beach and 1.4 miles from Anne's Beach.

  • Pelican Landing
    Breakfast options

    Pelican Landing is located in Islamorada, just a 12-minute walk from Sea Oats Beach and 1.4 miles from Anne's Beach.

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

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

    EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS in Islamorada provides accommodations with a private beach area, an outdoor swimming pool, and a garden.

  • Little Bay Cottage

    Little Bay Cottage offers accommodations in Islamorada, 2.7 miles from Windley Key and 13 miles from Pigeon Key. The air-conditioned accommodation is a 13-minute walk from Upper Matecumbe Key.

  • Little Bay Compound

    Just a 13-minute walk from Upper Matecumbe Key and 0.6 miles from History of Diving Museum, Little Bay Compound features accommodations in Islamorada with a garden.

  • Martin Family Fish Camp

    Martin Family Fish Camp offers accommodations in Islamorada, a 7-minute walk from Upper Matecumbe Key and 3 miles from Windley Key.

  • The Oasis
    Central location

    Just a 18-minute walk from Upper Matecumbe Key and half a mile from History of Diving Museum, The Oasis features accommodations in Islamorada with a garden.

  • 3 Lux Ensuites Walk Boat Island

    3 Lux Ensuites Walk Boat Island offers accommodations in Islamorada, a 5-minute walk from Upper Matecumbe Key and 3.4 miles from Windley Key.

  • Beacon Reef 503

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 503 features accommodations in Islamorada with a garden.

  • Beacon Reef 501

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 501 features accommodations in Islamorada with a garden.

  • Beacon Reef 406

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 406 features accommodations in Islamorada with a garden.

  • Beacon Reef 310

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 310 features accommodations in Islamorada with a garden.

  • Beacon Reef 307

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 307 features accommodations in Islamorada with a garden.

  • Beacon Reef 306

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 306 features accommodations in Islamorada with a garden.

  • Beacon Reef 301

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 301 features accommodations in Islamorada with a garden.

  • Beacon Reef 222

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 222 features accommodations in Islamorada with a garden.

  • Palms 417
    Central location

    Palms 417 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key. This beachfront property offers access to a terrace.

  • Palms 407
    Central location

    Palms 407 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 404
    Central location

    Palms 404 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 317
    Central location

    Palms 317 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 314
    Central location

    Palms 314 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 313
    Central location

    Palms 313 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 301
    Central location

    Palms 301 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 309
    Central location

    Palms 309 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Anglers Reef Vacation Rental

    Just a 5-minute walk from Windley Key and one mile from Windley Key Fossil Reef Geological State Park, Anglers Reef Vacation Rental features accommodations in Islamorada with barbecue facilities.

  • Lyons Landing
    Central location

    Lyons Landing offers accommodations in Islamorada, 1.6 miles from Windley Key and 4.8 miles from Upper Matecumbe Key.

  • Harbor House
    Central location

    Harbor House is located in Islamorada, just 1.4 miles from Windley Key and 4.7 miles from Upper Matecumbe Key.

  • Ocean Harbour K31

    Ocean Harbour K31 is located in Islamorada, just 2.7 miles from Windley Key and 6 miles from Upper Matecumbe Key.

  • Blue Water Retreat

    Blue Water Retreat offers accommodations in Islamorada, 1.3 miles from Sea Oats Beach and 5.9 miles from Upper Matecumbe Key. This beachfront property offers access to a balcony.

  • Beachfront Villa at Islamorada BY THE GLAMHOMES

    Providing an outdoor swimming pool, Beachfront Villa at Islamorada BY THE GLAMHOMES offers accommodations in Islamorada.

Villas That Guests Love in Islamorada

  • Avg. price/night: $684.23
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 246 reviews
    The villas were spacious and clean
    W
    William
    Family with young children
  • Avg. price/night: $381.38
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 814 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
  • Avg. price/night: $684.23
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 246 reviews
    The villas are so confortable and have all the amenities that we need
    Martina
    Group
  • Avg. price/night: $684.23
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 246 reviews
    The villas are nice enough, clean and comfortable. The pool area is absolutely phenomenal, particularly at sunset.
    A
    Anonymous
    Family with young children
  • Avg. price/night: $684.23
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 246 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
  • Avg. price/night: $398.25
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 830 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
  • Avg. price/night: $209.42
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,039 reviews
    Beachfront villa, beautiful location. Friendly staff
    G
    Glenn
    Family with young children
  • Avg. price/night: $684.23
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 246 reviews
    The villas were a great size to ensure a comfortable stay and well equipped in the kitchen. Having boat slips on property was a great Convenience. The property was beautiful and staff were very friendly.
    Jessica
    Family with young children
  • Avg. price/night: $209.42
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,039 reviews
    Everything was great, updated facilities and villas. Boat docks were great, perfect for fishing (mainly mangrove and yellowtail snapper). Saw nurse sharks, eels, and a manatee while fishing from the dock. Kayaks, paddleboards and bikes for use. Located close to lots of attractions and fantastic restaurants.
    Keri
    Family with young children
  • 9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 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