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Holiday Homes in Summerland Key

Find the holiday homes that appeal to you the most

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

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, 333 reviews

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, 38 reviews

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

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

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

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
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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Popular with guests booking holiday homes in Summerland Key

Popular with guests booking holiday homes in Summerland Key

Popular with guests booking holiday homes in Summerland Key

Popular with guests booking holiday homes in Summerland Key

Scored out of 10, guest rating 7.5
Good - What previous guests thought, 2 reviews

Popular with guests booking holiday homes in Summerland Key

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Popular with guests booking holiday homes in Summerland Key

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Popular with guests booking holiday homes in Summerland Key

Popular with guests booking holiday homes in Summerland Key

Popular with guests booking holiday homes in Summerland Key

Popular with guests booking holiday homes in Summerland Key

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 333 reviews

Holiday Homes with swimming pools in Summerland Key and nearby

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

From US$826.69 per night
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 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.

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, 38 reviews

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

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 10
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.

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

Sea La Vie

Cudjoe Key
Budget options available

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.

Tobago Stars

Little Torch Key
Budget options available

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.

Enjoy breakfast in Summerland Key and nearby

Hawkins Lookout

Cudjoe Key
Breakfast options

Featuring air-conditioned accommodation with a balcony, Hawkins Lookout is set in Cudjoe Key. Guests can benefit from a patio and an outdoor fireplace.

Situated in Cudjoe Key, The Mermaid Manor features accommodation with a private pool, a balcony and sea views. With pool views, this accommodation offers a patio.

L`archipel

Key West
Breakfast options

Located in Key West, 44 km from Ernest Hemingway Home and Museum and 44 km from Duval Street, L`archipel offers air conditioning.

Boasting air-conditioned accommodation with a private pool, Parrotfish Pointe is set in Cudjoe Key. This beachfront property offers access to a balcony.

Foster`s Folly

Key West
Breakfast options

Set in Key West, 42 km from Florida Keys Aquarium Encounters and 48 km from Ernest Hemingway Home and Museum, Foster`s Folly offers air conditioning.

Boasting air-conditioned accommodation with a balcony, Salty Air Retreat is situated in Little Torch Key. This holiday home also has a private pool.

Set in Little Torch Key, 40 km from Florida Keys Aquarium Encounters and 46 km from Ernest Hemingway Home and Museum, Blackbeard Retreat offers an outdoor swimming pool and air conditioning.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 4 reviews

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.

From US$655.51 per night

Holiday homes that guests love in Summerland Key

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Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 333 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