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

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

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

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

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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

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

20 MINUTES TO KEY WEST , BOATERS PARADISE

Private Secluded Ocean View & Pool Near Key West

Island Time #110 Ocean Views - Cudjoe Key
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 | 376 Holiday Homes |
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Lowest Price | NZ$188 |
Highest Price | NZ$1,050 |
Popular accommodation | JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, Old Florida Style, wrap around porch, boat basin for dockage, open water, Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security, Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel , 20 MINUTES TO KEY WEST , BOATERS PARADISE, Private Secluded Ocean View & Pool Near Key West, Island Time #110 Ocean Views - Cudjoe Key |
Top Locations for Holiday Homes in Summerland Key
More accommodations in Summerland Key
Top trending hotels in Summerland Key

Parmer's Resort

Sugar Loaf Lodge

Sugarloaf Key Hotel at KOA Resort

Looe Key Reef Resort
More ways to explore Summerland Key
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^Subject to availability and chosen travel dates.