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The best holiday homes in Summerland Key

Check out our pick of great holiday homes in Summerland Key

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Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Situated within 32 km of Ernest Hemingway Home and Museum and 32 km of Duval Street, Sun Outdoors Sugarloaf Key features rooms with air conditioning and a private bathroom in Summerland Key. Both free WiFi and parking on-site are accessible at the holiday home free of charge. Key West Aquarium is 32 km from the holiday home and Mallory Dock is 32 km away.

We had a great stay here. The staff were all very friendly and helpful. The grounds were beautiful and very clean. Our bungalow was very cute and beautifully decorated.

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9.3
Superb
69 reviews
Price from
£186
per night

This holiday home features 3 bedrooms, a kitchen with a dishwasher and an oven, a flat-screen TV, a seating area and 2 bathrooms fitted with a bath. Towels and bed linen are available in the holiday home. For added privacy, the accommodation features a private entrance.

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10
Exceptional
1 reviews

This air-conditioned holiday home is fitted with 2 bedrooms, a flat-screen TV, and a fully equipped kitchen with a dishwasher and an oven. Towels and bed linen are featured in the holiday home. For added privacy, the accommodation has a private entrance and is protected by full-day security.

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7
Good
4 reviews
Price from
£271
per night

Featuring sea views, NAUTILUS...ocean front cottage retreat ~ provides accommodation with a private beach area, pool with a view and a garden, around 37 km from Ernest Hemingway Home and Museum. This beachfront property offers access to tennis at the tennis court, free private parking and free WiFi. The property is non-smoking and is located 37 km from Duval Street.

Wonderful resort with many amenities. Loved the kayaks and bikes that were provided. Great location to explore the islands.

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9.2
Superb
13 reviews

Located in Cudjoe Key, 37 km from Ernest Hemingway Home and Museum and 37 km from Duval Street, OCEANIA... Water front cottage retreat ~ offers barbecue facilities and air conditioning. This villa features a private pool, a garden and free private parking. The villa has a picnic area and a sauna.

Location was great. Really enjoyed it

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9.3
Superb
10 reviews
Price from
£384
per night

Set in Cudjoe Key, 37 km from Ernest Hemingway Home and Museum and 37 km from Duval Street, Pelican's Roost, Waterfront comfort at Venture Out offers a private beach area and air conditioning. This beachfront property offers access to a balcony, tennis at the tennis court, free private parking and free WiFi. The holiday home offers a pool with a view with a fence, as well as a hot tub and a 24-hour front desk.

Very nice on the water with view of Atlantic

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9.3
Superb
10 reviews
Price from
£294
per night

The air-conditioned holiday home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with an a bath or shower and a hair dryer. Towels and bed linen are provided in the holiday home. The property has an outdoor dining area.

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8
Very good
3 reviews

Boasting air-conditioned accommodation with a private pool, quiet street view and a patio, Tree Top Paradise is set in Cudjoe Key. This property offers access to a balcony, pool at the pool table, free private parking and free WiFi. The holiday home features a hot tub and a 24-hour front desk.

The screened in porch was lovely! The whole place was beautifully decorated and comfortable. The palm trees and palms were surrounding the house and it was so nice. Would definitely stay here again!

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8.8
Fabulous
5 reviews
Price from
£245
per night

Featuring air-conditioned accommodation with a private pool, pool view and a patio, Ocean View with Pool, 4 bedroom Vila Near Key West is located in Cudjoe Key. This property offers access to a balcony, table tennis, free private parking and free WiFi. The villa has a hot tub and full-day security.

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10
Exceptional
2 reviews
Price from
£1,067
per night

With free WiFi, this holiday home features a cable TV, a washing machine and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the holiday home. For added privacy, the accommodation features a private entrance.

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Price from
£205
per night

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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  • Sun Outdoors Sugarloaf Key
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 69 reviews

    Situated within 32 km of Ernest Hemingway Home and Museum and 32 km of Duval Street, Sun Outdoors Sugarloaf Key features rooms with air conditioning and a private bathroom in Summerland Key.

    The property was excellent. Very comfortable and clean

  • Experience Coastal Living at its Best Florida Keys

    Offering sea views, Experience Coastal Living at its Best Florida Keys is an accommodation situated in Summerland Key, 42 km from Florida Keys Aquarium Encounters and 44 km from Ernest Hemingway Home...

  • Endless Summerland

    Set in Summerland Key, 39 km from Ernest Hemingway Home and Museum and 39 km from Duval Street, Endless Summerland offers air-conditioned accommodation with a balcony and free WiFi.

  • Relaxing 2 2 Get Away in the Lower Keys! home

    Boasting sea views, Relaxing 2 2 Get Away in the Lower Keys! home features accommodation with a balcony, around 42 km from Ernest Hemingway Home and Museum.

  • Salty Slumber Relaxing 2 bedroom 2 bath Get Away in the Lower Keys

    Boasting air-conditioned accommodation with a balcony, Salty Slumber Relaxing 2 bedroom 2 bath Get Away in the Lower Keys is set in Summerland Key.

  • Private Estate Pool Ocean View 20 minutes to Key West

    Boasting air-conditioned accommodation with a private pool, pool view and a patio, Private Estate Pool Ocean View 20 minutes to Key West is set in Summerland Key.

  • Skyway Living

    Located in Summerland Key, 41 km from Ernest Hemingway Home and Museum and 41 km from Duval Street, Skyway Living provides air-conditioned accommodation with a patio and free WiFi.

  • Summerland Canal

    Situated in Summerland Key, 41 km from Ernest Hemingway Home and Museum and 41 km from Duval Street, Summerland Canal features air-conditioned accommodation with a balcony and free WiFi.

Holiday homes that guests love in Summerland Key

  • 9.3
    Scored 9.3
    Superb
    Rated superb
     · 69 reviews
    We had a great stay here. The staff were all very friendly and helpful. The grounds were beautiful and very clean. Our bungalow was very cute and beautifully decorated.
    Lisa
    Young couple
  • Avg. price/night: £230.86
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 563 reviews
    Very clean and quiet room. Drinking the morning coffee in the balcony was one of the best part of my day. One of the best value accommodations close enough to Key West. The room was very spacious, clean and well equipped. Everything that a traveler needs was found in the room.
    Péter
    Family with young children
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