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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+
Our top picks Lowest price first Star rating and price Top reviewed

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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
25 reviews
Price from
£422
per night

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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9.4
Superb
29 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 barbecue facilities. This beachfront property offers access to table tennis, free private parking and free WiFi. Boasting family rooms, this property also provides guests with a children's playground.

Beautiful property and room was gorgeous and clean and bed was so comfy. Staff were as so friendly and accommodating.

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8.5
Very good
318 reviews
Price from
£236
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
£136
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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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
£1,807
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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Price from
£117
per night

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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Price from
£1,178
per night

The spacious holiday home features 6 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 5 bathrooms with a walk-in shower. Towels and bed linen are provided in the holiday home. The property has an outdoor dining area.

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Price from
£892
per night

Most booked holiday rentals in Islamorada this month

Enjoy breakfast in Islamorada!

  • Anglers Reef Getaway
    Breakfast options

    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

    9.0
    Scored 9.0
    Superb
    Rated superb
     · 25 reviews
  • Anglers Reef Paradise
    Breakfast options

    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.

    perfektes Südstaatenfeeling sehr exquisit und sicher

    9.4
    Scored 9.4
    Superb
    Rated superb
     · 29 reviews
  • Matecumbe Resort
    Breakfast options

    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 barbecue facilities.

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

    8.5
    Scored 8.5
    Very good
    Rated very good
     · 319 reviews
  • Tollgate Tides
    Breakfast options

    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
    Breakfast options

    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
    Breakfast options

    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
    Breakfast options

    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
    Breakfast options

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

These holiday rentals in Islamorada have options with FREE cancellation

  • Casa Koto
    Free cancellation options available

    Featuring air-conditioned accommodation with a patio, Casa Koto is located in Islamorada. This beachfront property offers access to a balcony and free WiFi.

  • Sun-kissed Bliss
    Free cancellation options available

    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.

  • EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
    Free cancellation options available

    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.

    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2 reviews
  • Paradise Beach
    Free cancellation options available

    Situated in Islamorada, just 80 metres from Sea Oats Beach, Paradise Beach features beachfront accommodation with a garden and free WiFi. The air-conditioned accommodation is 1.9 km from Anne's Beach.

FAQ about holiday rentals in Islamorada




Holiday rentals that guests love in Islamorada

  • Avg. price/night: £399.15
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 250 reviews
    The villas were spacious and clean
    W
    William
    Family with young children
  • Avg. price/night: £310.81
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 800 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: £245.95
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 1,267 reviews
    Our 2 storey pool villa was fabulous. Really liked the pool area and breakfast was nice in the lobby.
    Sarah
    Young couple
  • Avg. price/night: £310.81
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 800 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
  • 9.4
    Scored 9.4
    Superb
    Rated superb
     · 29 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
    Young couple
  • Avg. price/night: £244.02
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,038 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
    Group
  • Avg. price/night: £245.95
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 1,267 reviews
    pool and staff. pool villa unit was nice
    Trey
    Young couple
  • Avg. price/night: £395.41
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 816 reviews
    Our villa was beautiful with ocean views. The place was immaculate and spacious , the staff was so nice and accommodating. We had a wonderful stay.
    Gia
    Group
  • Avg. price/night: £245.95
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 1,267 reviews
    Spacious pool villa, helpful staff, nice swimming pool.
    Danique
    People with friends
gogless