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
Cudjoe Key FL
The price is AU$1,187 per night from 21 Apr to 22 Apr
AU$1,187
21 Apr - 22 Apr
includes taxes & fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Private Secluded Ocean View & Pool Near Key West
Summerland Key FL
With a stay at this vacation home in Summerland Key, you'll be by the sea, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key FL
The price is AU$1,005 per night from 5 Apr to 6 Apr
AU$1,005
5 Apr - 6 Apr
includes taxes & fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Save an average of 15% on thousands of hotels when you're signed in
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key FL
The price is AU$941 per night from 25 Mar to 26 Mar
AU$941
25 Mar - 26 Mar
includes taxes & fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key FL
The price is AU$1,196 per night from 29 Mar to 30 Mar
AU$1,196
29 Mar - 30 Mar
includes taxes & fees
Located in Summerland Key, this vacation home is by the ocean, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea ...
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Cudjoe Key FL
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Open water views! Golf cart included! Beautiful 2 bedroom house in Venture Out
Cudjoe Key FL
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Sunny Hideaway - Venture Out Unit 276
Summerland Key FL
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Beachside @ Torchview Waterfront Retreat
Summerland Key FL
With a stay at this vacation home in Summerland Key, you'll be on the beach, within a 15-minute drive of Florida Keys Beaches and National Key Deer Refuge Visitor ...
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 | 371 Holiday Homes |
|---|---|
Lowest Price | AU$333 |
Highest Price | AU$1,196 |
Popular accommodation | Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Private Secluded Ocean View & Pool Near Key West, Cudjoe Cottages, swimming pool, just 20 miles from Key West, 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, Open water views! Golf cart included! Beautiful 2 bedroom house in Venture Out , Sunny Hideaway - Venture Out Unit 276, Beachside @ Torchview Waterfront Retreat |
Top trending hotels in Summerland Key
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
With a stay at Sugarloaf Key Hotel at KOA Resort in Summerland Key, you'll be 7.2 mi (11.5 km) from Florida Keys Beaches and 16.2 mi (26.1 km) from Florida Keys ...
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is AU$333 per night from 24 Mar to 25 Mar
AU$333
24 Mar - 25 Mar
includes taxes & fees
With a stay at Parmer's Resort in Summerland Key, you'll be on the waterfront, within a 15-minute drive of Florida Keys Beaches and National Key Deer Refuge ...
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
Located in Summerland Key, Looe Key Reef Resort is by the ocean, a 4-minute drive from Florida Keys Beaches and 5 minutes from National Key Deer Refuge Visitor ...
Save an average of 15% on thousands of hotels when you're signed in
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is AU$399 per night from 23 Mar to 24 Mar
AU$399
23 Mar - 24 Mar
includes taxes & fees
With a stay at Sugar Loaf Lodge in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Sound.
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.