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The best vacation homes in Islamorada

Check out our selection of great vacation homes in Islamorada

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Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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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
Wonderful
24 reviews
Price from
$466.67
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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9.3
Wonderful
24 reviews
Price from
$320
per night

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, Htd Pool, Dock, Walkable.

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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 Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!.

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Price from
$678.50
per night

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
$466.41
per night

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
$441.76
per night

Located in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable 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
$431.09
per night

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
$358.80
per night

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
$378.51
per night

Boasting air-conditioned accommodation with a balcony, Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location is situated in Islamorada. The property is located 1 km from Upper Matecumbe Key, 4.3 km from Windley Key and 20 km from Pigeon Key. The holiday home has parking on-site, a fitness room and a 24-hour front desk.

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Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.
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  • Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

    Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

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

    Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location is located in Islamorada, just a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

  • Peaceful Palms A2
    Budget options available

    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
    Budget options available

    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
    Budget options available

    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
    Budget options available

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

  • Sandglass 4
    Budget options available

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

  • Pelican Landing
    Budget options available

    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 vacation homes 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 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.

  • Executive Bay Club Condos

    Executive Bay Club Condos is located in Islamorada, just 5.6 miles from Upper Matecumbe Key and 8 miles from Pigeon Key. This vacation home features accommodations with a patio.

  • 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.

  • Waterfront Wonder

    Waterfront Wonder is located in Islamorada, just 1.5 miles from Anne's Beach and 7.6 miles from Upper Matecumbe Key. Guests may go for a swim in the private pool.

FAQ about vacation homes in Islamorada


Vacation Homes That Guests Love in Islamorada

  • Avg. price/night: $252
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 860 reviews
    The hotel is absolutely beautiful, we’ve stayed in a room just right on the beach it was like a dream. Rooms are very clean. There’s bar on the pool area. There’s a nice restaurant and cafe so close to hotel.
    BETUL
    Young couple
  • Avg. price/night: $219.37
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 1,177 reviews
    The property was very well maintained very clean.
    Harry
    Young couple
  • Avg. price/night: $190.13
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 815 reviews
    It was very clean and nice pool area , staff very welcoming .
    Joanne
    Young couple
  • Avg. price/night: $372.94
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 4 reviews
    Very clean. Friendly staff. Great location!
    Richard
    Solo traveler
  • 8.0
    Scored 8.0
    Very Good
    Rated very good
     · 380 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
  • Avg. price/night: $514.35
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 164 reviews
    The location is very beautiful, right by the water. The property was very clean and well maintained.
    Tom
    Family with young children
  • Avg. price/night: $231.75
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 394 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
  • Avg. price/night: $358.88
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 838 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
  • Avg. price/night: $347.63
    7.8
    Scored 7.8
    Good
    Rated good
     · 1,044 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
  • Avg. price/night: $219.37
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 1,177 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
gogless