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Holiday Homes in Islamorada

Find the holiday homes that appeal to you the most

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The best holiday homes in Islamorada

Check out our pick of great holiday homes in Islamorada

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Anglers Reef Getaway, holiday home in Islamorada

Featuring air-conditioned accommodation with a pool with a view, garden view and a patio, Anglers Reef Getaway is set in Islamorada. This beachfront property offers access to a balcony, squash on the squash court, free private parking and free WiFi. The property is non-smoking and is situated 600 metres from Windley Key.

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, holiday home in Islamorada

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.

Location & the grounds & pool were amazing.

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9.3
Superb
24 reviews
Price from
£305
per night
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Isla Tamarillo - Waterfront Boutique Resort, Island Paradise, Prime Location, holiday home in Islamorada

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
£435
per night
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Isla Mirabelle - Waterfront Boutique Resort, Island Paradise, Prime Location, holiday home in Islamorada

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, holiday home in Islamorada

Located in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location provides air-conditioned accommodation with a balcony and free WiFi. The property is set 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation offers a 24-hour front desk and parking on-site.

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Price from
£425
per night
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Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location, holiday home in Islamorada

Set in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location offers air-conditioned accommodation with a balcony and free WiFi. The property is located 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation provides a 24-hour front desk and parking on-site.

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Price from
£428
per night
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Isla Key Lime - Island Paradise, Waterfront Pool, Prime Location, holiday home in Islamorada

Located in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Lime - Island Paradise, Waterfront Pool, Prime Location provides air-conditioned accommodation with a balcony and free WiFi. The property is situated 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation features a 24-hour front desk and parking on-site.

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Price from
£419
per night
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Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location, holiday home in Islamorada

Situated in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location features air-conditioned accommodation with a balcony and free WiFi. The property is located 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation provides a 24-hour front desk and parking on-site.

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Price from
£401
per night
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Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location, holiday home in Islamorada

Set in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location offers air-conditioned accommodation with a balcony and free WiFi. The property is situated 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation features a 24-hour front desk and parking on-site.

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Price from
£415
per night
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Peaceful Palms A2, holiday home 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
£317
per night
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All holiday homes in Islamorada

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
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Save money on holiday homes in Islamorada – budget options available!

  • Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

    Set in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location offers air-conditioned accommodation with a...

  • Peaceful Palms A2
    Budget options available

    Set in Islamorada, less than 1 km from Windley Key and 5 km from Upper Matecumbe Key, Peaceful Palms A2 offers air-conditioned accommodation with a terrace and free WiFi.

  • West Plaza Del Lago
    Budget options available

    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
    Budget options available

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

  • Sunshine Place
    Budget options available

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

  • Sandglass 4
    Budget options available

    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
    Budget options available

    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.

  • Palms 417
    Budget options available

    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.

Great access to the city centre! Check these holiday homes 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.

  • 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.

  • 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.

  • Blue Water Retreat

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

  • 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.

  • Waterfront Wonder

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

  • Antigua Place
    Central location

    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.

Holiday homes that guests love in Islamorada

  • Breezy Palms Resort

    Breezy Palms Resort

    Holiday Home in Islamorada
    Avg. price/night: £149.80
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 1,123 reviews
    The property was very well maintained very clean.
    Harry
    Young couple
  • Sunset Inn

    Sunset Inn

    Holiday Home in Islamorada
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 822 reviews
    It was very clean and nice pool area , staff very welcoming .
    Joanne
    Young couple
  • Casa Morada

    Casa Morada

    Holiday Home in Islamorada
    Avg. price/night: £293.08
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 2 reviews
    Very clean. Friendly staff. Great location!
    Richard
    Solo traveller
  • Drop Anchor Resort & Marina

    Drop Anchor Resort & Marina

    Holiday Home in Islamorada
    Avg. price/night: £310.23
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 385 reviews
    Daniel was super helpful. Beautiful place with lots of colorful buildings, small but perfect pool for kids, very clean appartments.
    Samuel
    Family with young children
  • Ragged Edge Resort & Marina

    Ragged Edge Resort & Marina

    Holiday Home in Islamorada
    Avg. price/night: £384.05
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 166 reviews
    The location is very beautiful, right by the water. The property was very clean and well maintained.
    Tom
    Family with young children
  • Sands of Islamorada

    Sands of Islamorada

    Holiday Home in Islamorada
    Avg. price/night: £163.56
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 389 reviews
    Really nice comfortable room. Very pleased to see reusable crockery and cutlery rather than the plastic throw away items used in most accommodations. Very clean and beautifully decorated. Only 3 miles from Robbie's Marina which is good fun. Walking distance (30 mins) to Florida Keys Brewery. Nice beach area and pool.
    Imogen
    Young couple
  • Chesapeake Beach Resort

    Chesapeake Beach Resort

    Holiday Home in Islamorada
    Avg. price/night: £264.34
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 834 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
  • Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    Holiday Home in Islamorada
    Avg. price/night: £183.89
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,036 reviews
    Loved sitting on patio wonderful view. Watched Pelicans diving in the water. Big comfortable room very clean and modern. Easy parking. Friendly staff at check in.
    Joanne
    Family with young children
  • Breezy Palms Resort

    Breezy Palms Resort

    Holiday Home in Islamorada
    Avg. price/night: £149.80
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 1,123 reviews
    Location was great! Room was very clean and comfortable. A beautiful setting with a beach as well. Each room has a small screen porch. Great value for the money! We would have liked a shade to darken the room though. We arrived late and wanted to sleep in a little and the sun streamed in. Thanks much.
    Elizabeth
    Young couple
  • Sunset Inn

    Sunset Inn

    Holiday Home in Islamorada
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 822 reviews
    It was very clean great room,beautiful heated pool ,kindfull staff .l
    Konstantinos
    Young couple

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