Book Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key

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
The price is NZ$1,093 per night from 25 Apr to 26 Apr
NZ$1,093
includes taxes & fees
25 Apr - 26 Apr
Stay at this vacation home in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key
The price is NZ$1,050 per night from 11 Apr to 12 Apr
NZ$1,050
includes taxes & fees
11 Apr - 12 Apr
Stay at this vacation home in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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
Stay at this vacation home in Summerland Key. Enjoy free WiFi, concierge services, and tennis courts. Popular attractions Florida Keys Beaches and Venture Key ...
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
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COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, concierge services, and tennis courts. Popular attractions Florida Keys Beaches and Venture Key ...
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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
Stay at this vacation home in Summerland Key. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Big Pine Key Flea Market ...
Old Florida Style, wrap around porch, boat basin for dockage, open water
One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.

Summerland Key
Book a stay at this beach vacation home in Summerland Key. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Crab Key and Pye Key are located ...
One of the very few beach houses with a daily, rental license in the Keys.
Just 20 miles from Key West!  Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Our guests praise the property condition ...
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

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

Cudjoe
Stay at this vacation home in Summerland Key. Enjoy free WiFi, tennis courts, and a pool table. Our guests praise the helpful staff in our reviews. Popular attractions ...
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

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

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, balconies, and an in-room coffeemaker. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Oceanfront home-shared swimming pool, dockage-just 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
355 Holiday Homes
Lowest Price
NZ$339
Highest Price
NZ$1,093
Popular accommodation
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, Cudjoe Cottages, swimming pool, just 20 miles from Key West, JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!, COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!, Old Florida Style, wrap around porch, boat basin for dockage, open water, One of the very few beach houses with a daily, rental license in the Keys., Just 20 miles from Key West! Oceanfront, dockage, swimming pool, 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

Top trending hotels in Summerland Key

Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$339 per night from 23 Apr to 24 Apr
NZ$339
includes taxes & fees
23 Apr - 24 Apr
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the bar and the helpful staff in our reviews. ...
Looe Key Reef Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939, Summerland Key, FL
Stay at this 3-star hotel in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our ...
Sugarloaf Key Hotel at KOA Resort
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 NZ$449 per night from 6 Apr to 7 Apr
NZ$449
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Parmer's Resort
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Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$392 per night from 30 Mar to 31 Mar
NZ$392
includes taxes & fees
30 Mar - 31 Mar
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Sugar Loaf Lodge
Don't see what you're looking for?
See all available properties in Summerland Key
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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.