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The 10 Best Holiday Rentals in Islamorada, USA

Check out our pick of great holiday rentals in Islamorada

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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The villa with a terrace and pool views features 2 bedrooms, 2 living rooms, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the villa. The property has an outdoor dining area.

loved the location and the quick responses from the host.

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9
Superb
24 reviews

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.

The holiday home includes a barbecue. There is a a terrace at this property and guests can go snorkelling, fishing and diving nearby. Two kayaks and 2 bicycles are offered. A boat hire is available for a surcharge.

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
Superb
25 reviews
Price from
£246
per night

Situated 1.9 km from Sea Oats Beach, Matecumbe Resort offers 2-star accommodation in Islamorada and has a private beach area, an outdoor swimming pool and a garden. This beachfront property offers access to table tennis, free private parking and free WiFi. The property offers allergy-free units and is located 9.2 km from Upper Matecumbe Key.

wow booked last minute, right on the little beach , beautiful views from windows, everything you need.

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8.5
Very good
324 reviews
Price from
£147
per night

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. This holiday home offers a private beach area, a garden, as well as a tennis court. The property features a year-round outdoor pool with a pool bar and is set 9.1 km from Upper Matecumbe Key.

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8.5
Very good
2 reviews
Price from
£125
per night

The spacious holiday home with a balcony and sea views features 2 bedrooms, a living room, a TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area.

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Price from
£196
per night

Set in Islamorada, 1.1 km from Sea Oats Beach and 10 km from Upper Matecumbe Key, Beachfront Villa at Islamorada BY THE GLAMHOMES offers a private beach area and air conditioning. This beachfront property offers access to a balcony, free private parking and free WiFi. On clear days, guests can head outside to enjoy the villa's outdoor fireplace or simply kick back and relax.

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Price from
£1,851
per night

Set in Islamorada, 1.2 km from Sea Oats Beach and 2.2 km from Anne's Beach, Plaza Del Sol offers air-conditioned accommodation with a terrace and free WiFi. This holiday home features accommodation with a balcony. The property is non-smoking and is situated 13 km from Upper Matecumbe Key.

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The holiday home features 2 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area.

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The spacious holiday home has 6 bedrooms, 6 bathrooms, bed linen, towels, a TV with cable channels, a dining area, a fully equipped kitchen, and a balcony with sea views. Guests can take in the ambience of the surroundings from an outdoor dining area or keep themselves warm by the fireplace on colder days. For added privacy, the accommodation features a private entrance.

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Set in Islamorada, a few steps from Sea Oats Beach and 1.6 km from Anne's Beach, Sun-kissed Bliss offers air-conditioned accommodation with a balcony and free WiFi. This holiday home features accommodation with a patio. The property is non-smoking and is situated 13 km from Upper Matecumbe Key.

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Price from
£252
per night

Most booked hotels in Islamorada in the past month

Islamorada's best hotels with breakfast

  • Anglers Reef Getaway
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 24 reviews

    Featuring air-conditioned accommodation with a pool with a view, garden view and a patio, Anglers Reef Getaway is set in Islamorada.

    The amenities,the location, the villas and the pool

  • Anglers Reef Paradise
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 25 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.

    Location & the grounds & pool were amazing.

  • Matecumbe Resort
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 324 reviews

    Situated 1.9 km from Sea Oats Beach, Matecumbe Resort offers 2-star accommodation in Islamorada and has a private beach area, an outdoor swimming pool and a garden.

    El lugar es súper bonito! Y es Perfecto para la familia

  • Tollgate Tides

    Set in Islamorada, 500 metres from Anne's Beach and 1.7 km from Sea Oats Beach, Tollgate Tides offers air-conditioned accommodation with a patio and free WiFi.

  • Beachfront Villa at Islamorada BY THE GLAMHOMES

    Set in Islamorada, 1.1 km from Sea Oats Beach and 10 km from Upper Matecumbe Key, Beachfront Villa at Islamorada BY THE GLAMHOMES offers a private beach area and air conditioning.

  • Plaza Del Sol

    Set in Islamorada, 1.2 km from Sea Oats Beach and 2.2 km from Anne's Beach, Plaza Del Sol offers air-conditioned accommodation with a terrace and free WiFi.

  • Two White Turtles

    Located in Islamorada, less than 1 km from Anne's Beach and a 17-minute walk from Sea Oats Beach, Two White Turtles provides air-conditioned accommodation with a patio and free WiFi.

  • Waterfront Wonder

    Boasting air-conditioned accommodation with a private pool, pool view and a patio, Waterfront Wonder is set in Islamorada.

FAQs about hotels in Islamorada






Holiday rentals that guests love in Islamorada

  • From £345.84 per night
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 475 reviews
    We didn't get the villa on the beach that we paid for, but they did upgrade us to what was probably a more comfortable 2 BR, 2 bath small house.
    Norm
    United States
  • From £257.55 per night
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 1,542 reviews
    Last year we stayed there and it was great, location, resort, staff and weather. This year was meh. Service at the poolside restaurant was spotty. They renamed the villages causing confusion so this year is was meh.
    Ron Moz Sr
    United States
  • From £240.39 per night
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 827 reviews
    Villa was lovely, spacious and comfortable! Great location overlooking the sea.
    Yasmina123
    United Kingdom
  • From £300.44 per night
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 245 reviews
    The villas were spacious and clean
    W
    William
    United States
  • From £240.39 per night
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 827 reviews
    The layout and I like that’s acomplete boutique hotel unique great staff and absolutely great planned villas n rooms
    ventura
    United States
  • From £192.29 per night
    7.0
    Scored 7.0
    Good
    Rated good
     · 1,227 reviews
    Our 2 storey pool villa was fabulous. Really liked the pool area and breakfast was nice in the lobby.
    Sarah
    United Kingdom
  • From £240.39 per night
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 827 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
    United States
  • 9.2
    Scored 9.2
    Superb
    Rated superb
     · 25 reviews
    The villa was well located and well appointed. From beach towels to kitchen appliances, from dishes to kayaks and bikes, this place seemed designed with our comfort and relaxation in mind.
    Anne
    United States
  • From £199.29 per night
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,045 reviews
    Brandon did a terrific job checking us in. When he found out one of us was blind he changed us from upstairs to a villa! Told us about all the amenities and even suggested a fishing guide. Great job! View was fantastic also!!!)
    Debbi
    United States
  • From £300.44 per night
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 245 reviews
    The villas are so confortable and have all the amenities that we need
    Martina
    United States