Book Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key

Private Secluded Ocean View & Pool Near Key West

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.
Opens in a new windowPrivate Secluded Ocean View & Pool Near Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, 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.
Opens in a new windowCudjoe Cottages, swimming pool, just 20 miles from Key West
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS

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 ...
Opens in a new windowOCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
Save an average of 15% on thousands of hotels when you're signed in
Tranquility Bayview House-Ocean Front with boat basin and boat ramp

Tranquility Bayview House-Ocean Front with 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 ...
Opens in a new windowTranquility Bayview House-Ocean Front with boat basin and boat ramp
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

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

Cudjoe 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.
Opens in a new windowJUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

Little Torch Key FL
The price is AU$1,337 per night from 1 Jan to 2 Jan
AU$1,337
1 Jan - 2 Jan 2026
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 ...
Opens in a new windowOld Florida Style, wrap around porch, boat basin for dockage, open water
Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

Cudjoe Key FL
With a stay at this vacation home in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Opens in a new windowOcean 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!

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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.
Opens in a new windowNOV. & 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

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

Cudjoe Key FL
The price is AU$913 per night from 19 Dec to 20 Dec
AU$913
19 Dec - 20 Dec
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.
Opens in a new windowDirect Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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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
413 Holiday Homes
Lowest Price
AU$168
Highest Price
AU$1,337
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

Parmer's Resort

2.5 out of 5
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is AU$370 per night from 19 Dec to 20 Dec
AU$370
19 Dec - 20 Dec
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 ...
Opens in a new windowParmer's Resort
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
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 ...
Opens in a new windowLooe Key Reef Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy Summerland Key FL
The price is AU$168 per night from 19 Dec to 20 Dec
AU$168
19 Dec - 20 Dec
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.
Opens in a new windowSugar Loaf Lodge
Save an average of 15% on thousands of hotels when you're signed in
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
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 ...
Opens in a new windowSugarloaf Key Hotel at KOA Resort
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.