Book Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, balconies, and an in-room coffeemaker. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, patios, and air conditioning. Popular attractions Venture Key and Venture Out Keys are located ...
Kelly's Kabin - Adorable Private Summerland Key Cottage
20 MINUTES TO KEY WEST , BOATERS PARADISE

20 MINUTES TO KEY WEST , BOATERS PARADISE

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, a pool table, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. ...
20 MINUTES TO KEY WEST , BOATERS PARADISE
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WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Cudjoe Key
The price is NZ$915 per night from 5 Dec to 6 Dec
NZ$915
includes taxes & fees
5 Dec - 6 Dec
Book a stay at this family-friendly vacation home in Summerland Key. Enjoy parking (surcharge), laundry facilities, and tennis courts. Popular attractions Florida ...
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, concierge services, and tennis courts. Popular attractions Florida Keys Beaches and Venture Key ...
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Cudjoe Key
Book a stay at this family-friendly vacation home in Summerland Key. Enjoy tennis courts, patios, and cable/satellite TV service. Popular attractions Florida ...
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Just 20 miles from Key West!  Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cudjoe Key
The price is NZ$907 per night from 22 Dec to 23 Dec
NZ$907
includes taxes & fees
22 Dec - 23 Dec
Stay at this vacation home in Summerland Key. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Our guests praise the property condition ...
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Walk to  Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, tennis courts, and a pool table. Popular attractions Florida Keys Beaches and Venture Key are ...
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Latitudes - Ocean front with pool

Latitudes - Ocean front with pool

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, private pools, and a garden. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
Latitudes - Ocean front with pool
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Summerland Key Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Summerland Key vacation homes are the perfect way for you to wing it.

Holiday houses in Summerland Key let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Summerland Key in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Summerland Key adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Summerland Key with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Summerland Key vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Summerland Key Holiday Homes essential information

Accommodation
283 Holiday Homes
Lowest Price
NZ$228
Highest Price
NZ$915
Popular accommodation
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Kelly's Kabin - Adorable Private Summerland Key Cottage, 20 MINUTES TO KEY WEST , BOATERS PARADISE, WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS, COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!, Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West, Just 20 miles from Key West! Oceanfront, dockage, swimming pool, Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear, Latitudes - Ocean front with pool

Top trending hotels in Summerland Key

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$262 per night from 3 Dec to 4 Dec
NZ$262
includes taxes & fees
3 Dec - 4 Dec
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939, Summerland Key, FL
Stay at this 3-star hotel in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our ...
Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$232 per night from 2 Dec to 3 Dec
NZ$232
includes taxes & fees
2 Dec - 3 Dec
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the bar and the helpful staff in our reviews. ...
Looe Key Reef Resort
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Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$228 per night from 1 Dec to 2 Dec
NZ$228
includes taxes & fees
1 Dec - 2 Dec
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Sugar Loaf Lodge
Don't see what you're looking for?
See all available properties in Summerland Key
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.