Book Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key

Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

Summerland Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowPrivate Secluded Ocean View & Pool Near Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy a garden, laundry facilities and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
Opens in a new windowCudjoe Cottages, swimming pool, just 20 miles from Key West
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS

OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS

Little Torch Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Big Pine Key Flea Market and Blue ...
Opens in a new windowOCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
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Tranquility Bayview House-Ocean Front with boat basin and boat ramp

Tranquility Bayview House-Ocean Front with boat basin and boat ramp

Little Torch Key FL
Stay at this holiday home in Summerland Key. Enjoy laundry facilities, patios and air conditioning. Popular attractions Big Pine Key Flea Market and Blue Hole ...
Opens in a new windowTranquility Bayview House-Ocean Front with boat basin and boat ramp
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and concierge services. Popular attractions Florida Keys Beaches and Venture ...
Opens in a new windowJUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Little Torch Key FL
Stay at this holiday home in Summerland Key. Enjoy a garden, laundry facilities and cable/satellite TV service. Popular attractions Big Pine Key Flea Market ...
Opens in a new windowOld Florida Style, wrap around porch, boat basin for dockage, open water
Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy private pools, a fitness centre and laundry facilities. Popular attractions Florida Keys Beaches and Upper ...
Opens in a new windowOcean View 4/2 Estate with Private Pool 15 minutes from Key West
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key FL
Stay at this family-friendly holiday home in Summerland Key. Enjoy parking (surcharge), laundry facilities and tennis courts. Popular attractions Florida Keys ...
Opens in a new windowNOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy a garden, laundry facilities and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
Opens in a new windowDirect Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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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
411 Holiday Homes
Lowest Price
NZ$370
Highest Price
NZ$484
Popular accommodation
Private Secluded Ocean View & Pool Near Key West, Cudjoe Cottages, swimming pool, just 20 miles from Key West, OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS, Tranquility Bayview House-Ocean Front with boat basin and boat ramp, JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!, Old Florida Style, wrap around porch, boat basin for dockage, open water, Ocean View 4/2 Estate with Private Pool 15 minutes from Key West, NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Top trending hotels in Summerland Key

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue Summerland Key FL
The price is NZ$370 per night from 18 Dec to 19 Dec
NZ$370
18 Dec - 19 Dec
includes taxes & fees
Stay at this beach motel in Summerland Key. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
Opens in a new windowParmer's Resort
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the bar and the helpful staff in their reviews. ...
Opens in a new windowLooe Key Reef Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy Summerland Key FL
The price is NZ$484 per night from 17 Jan to 18 Jan
NZ$484
17 Jan - 18 Jan 2026
includes taxes & fees
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a marina. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSugar Loaf Lodge
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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 hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSugarloaf Key Hotel at KOA Resort
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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.

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^Subject to availability and chosen travel dates.