Book Holiday Homes in Summerland Key
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Featured Holiday Homes in Summerland Key

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
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

Looe Key Reef Resort

Sugar Loaf Lodge

Sugarloaf Key Hotel at KOA Resort
More ways to explore Summerland Key
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^Subject to availability and chosen travel dates.
