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

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

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

Fandango - private pool

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Private Secluded Ocean View & Pool Near Key West

Mini lobster available! Open Water View from porch , dock, bikes, kayaks

Lower Keys paradise

Old Florida Style, wrap around porch, boat basin for dockage, open water
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 | 368 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel , Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Fandango - private pool, Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community, Private Secluded Ocean View & Pool Near Key West, Mini lobster available! Open Water View from porch , dock, bikes, kayaks, Lower Keys paradise, Old Florida Style, wrap around porch, boat basin for dockage, open water |
Top Locations for Holiday Homes in Summerland Key
More accommodations in Summerland Key
Top trending hotels in Summerland Key

Parmer's Resort

Sugarloaf Key Hotel at KOA Resort

Looe Key Reef Resort

Sugar Loaf Lodge
More ways to explore Summerland Key
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.