The 10 best holiday homes in Summerland Key, USA | Booking.com
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Holiday Homes in Summerland Key

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Find the right holiday home for you in Summerland Key

The best holiday homes in Summerland Key

Check out our pick of great holiday homes in Summerland Key

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Island Oasis ~ YOUR Paradise Awaits!

Cudjoe Key (Near Summerland Key)

Set in Cudjoe Key, Island Oasis ~ YOUR Paradise Awaits! offers accommodation with a private pool, a balcony and sea views. A hot tub is available for guests.

A
Ani
From
Croatia
Good location, close to Key West and other attractions across the Keys. Quiet neighborhood. Helpful hosts and receptionists. Very cozy place, with a nice terrace, lovely view, comfortable rooms and well-equipped. We enjoyed our stay.
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5 reviews
Price from
US$335.70
1 night, 2 adults
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Sugarloaf Key RV Resort & Cottages

Summerland Key

Situated in Summerland Key, 32 km from Ernest Hemingway Home and Museum, Sugarloaf Key RV Resort & Cottages features air-conditioned rooms with free WiFi.

M
Mariusz
From
Poland
Very clean, almost new cottage.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 329 reviews
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Tree Top Paradise

Cudjoe Key (Near Summerland Key)

Boasting air-conditioned accommodation with a private pool, quiet street view and a patio, Tree Top Paradise is set in Cudjoe Key.

A
Amanda
From
United States
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!
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 35 reviews
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Pelican's Roost, Waterfront comfort at Venture Out

Cudjoe Key (Near Summerland Key)

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.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 21 reviews
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NAUTILUS...ocean front cottage retreat ~

Cudjoe Key (Near Summerland Key)

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.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 18 reviews
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OCEANIA... water front cottage retreat ~

Cudjoe Key (Near Summerland Key)

37 km from Ernest Hemingway Home and Museum in Cudjoe Key, OCEANIA... Water front cottage retreat ~ offers accommodation with access to a sauna and hot tub.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 18 reviews
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Dock Holiday

Cudjoe Key (Near Summerland Key)

Featuring air-conditioned accommodation with a heated pool, Dock Holiday is located in Cudjoe Key. A hot tub is available for guests. The property features a restaurant with an outdoor dining area.

K
Kris Thomas Booking.com
From
United States
The location was behind a 24 hour security gate with someone at the gate 27/7. Our unit was clean and right on the a canal. It had a full kitchen stocked with all the pots, pans, and silverware you would ever need. The unit had dishwasher, washing machine and dryer. The larger property complex our unit was in had beach access, a pool and laundry facilities.
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 6 reviews
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All holiday homes in Summerland Key

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.

Most booked holiday homes in Summerland Key and surroundings in the past month

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Save money on holiday homes in Summerland Key and nearby – budget options available

  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 2 reviews

    Set in Cudjoe Key, Turtle Cove Views by Last Key Realty provides accommodation with a heated pool.

  • Situated in Cudjoe Key, Tidewater Views by Last Key Realty offers a heated pool.

  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 5 reviews

    Set in Cudjoe Key, Island Oasis ~ YOUR Paradise Awaits! offers accommodation with a private pool, a balcony and sea views. A hot tub is available for guests.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 18 reviews

    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.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 18 reviews

    37 km from Ernest Hemingway Home and Museum in Cudjoe Key, OCEANIA... Water front cottage retreat ~ offers accommodation with access to a sauna and hot tub.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 21 reviews

    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.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set in Cudjoe Key, Mermaid Magic by Last Key Realty provides accommodation with a heated pool.

  • Paradise Found

    Key West
    Budget options available

    Located in Key West, 37 km from Duval Street and 37 km from Southernmost Point, Paradise Found offers air conditioning.

Enjoy breakfast in Summerland Key and nearby

  • Dock Holiday

    Cudjoe Key
    Breakfast options
    Scored out of 10, guest rating 7.1
    Good - What previous guests thought, 6 reviews

    Featuring air-conditioned accommodation with a heated pool, Dock Holiday is located in Cudjoe Key. A hot tub is available for guests. The property features a restaurant with an outdoor dining area.

  • Situated in Cudjoe Key, Dolphin Daydreams by Last Key Realty offers accommodation with a heated pool.

  • Boasting air-conditioned accommodation with a patio, Oceanview Retreat with 60ft Seawall is situated in Cudjoe Key.

    From US$1,052.26 per night

  • Serenity Now Seaside Escape - Brand New Build! is set in Cudjoe Key, 38 km from Ernest Hemingway Home and Museum, 38 km from Duval Street, as well as 38 km from Southernmost Point.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 35 reviews

    Boasting air-conditioned accommodation with a private pool, quiet street view and a patio, Tree Top Paradise is set in Cudjoe Key.

  • Sea La Vie

    Cudjoe Key
    Breakfast options

    Set just 38 km from Southernmost Point, Sea La Vie provides accommodation in Cudjoe Key with access to massage services, a terrace, as well as an ATM.

  • Situated in Cudjoe Key, Carefree on Cudjoe by Last Key Realty features accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Featuring air-conditioned accommodation with a patio, Tobago Stars is located in Little Torch Key. Spa facilities is available for guests. The property has a restaurant with an outdoor dining area.

Holiday homes that guests love in Summerland Key

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  • Sugarloaf Key RV Resort & Cottages

    Holiday Home in Summerland Key
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 329 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.
    Guest review by
    Lisa
    Young couple

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