Book Holiday Homes in Summerland Key
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Featured Holiday Homes in Summerland Key
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
With a stay at Sugarloaf Key RV Resort & Cottages in Summerland Key, you'll be within a 15-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
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.
Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key FL
The price is AU$1,151 per night from 2 June to 3 June
AU$1,151
2 June - 3 June
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key FL
The price is AU$629 per night from 27 May to 28 May
AU$629
27 May - 28 May
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 Venture Out Keys.
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Cudjoe FL
With a stay at this vacation home in Summerland Key, you'll be near the beach, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views 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.
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key FL
The price is AU$781 per night from 18 May to 19 May
AU$781
18 May - 19 May
includes taxes & fees
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.
Tranquility Bayview House-Ocean Front with pool, boat basin and boat ramp
Little Torch Key FL
With a stay at this vacation home in Summerland Key, you'll be within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea ...
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
Little Torch Key FL
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 ...
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 | 393 Holiday Homes |
|---|---|
Lowest Price | AU$262 |
Highest Price | AU$1,151 |
Popular accommodation | Sugarloaf Key RV Resort & Cottages, Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Old Florida Style, wrap around porch, boat basin for dockage, open water, Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!, Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out, SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!, Tranquility Bayview House-Ocean Front with pool, boat basin and boat ramp, OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS |
Top trending hotels in Summerland Key
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is AU$268 per night from 18 May to 19 May
AU$268
18 May - 19 May
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 ...
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 ...
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is AU$262 per night from 14 June to 15 June
AU$262
14 June - 15 June
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.
Save an average of 15% on thousands of hotels when you're signed in
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
With a stay at Sugarloaf Key RV Resort & Cottages in Summerland Key, you'll be within a 15-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
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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**Terms and Conditions apply.
^Subject to availability and chosen travel dates.