Book Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key

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
The price is NZ$1,541 per night from 10 Mar to 11 Mar
NZ$1,541
includes taxes & fees
10 Mar - 11 Mar
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
Beachside @ Torchview Waterfront Retreat

Beachside @ Torchview Waterfront Retreat

Summerland Key
Book a stay at this beach vacation home in Summerland Key. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Blue Hole and Crab Key are located ...
Beachside @ Torchview Waterfront Retreat
3 night minimum! Spectacular Ocean Views!

3 night minimum! Spectacular Ocean Views!

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, a pool table, and patios. Popular attractions Florida Keys Beaches and Venture Key are located ...
3 night minimum! Spectacular Ocean Views!
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Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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

Cudjoe Key
Book a stay at this family-friendly vacation home in Summerland Key. Enjoy free WiFi, tennis courts, and a picnic area. Popular attractions Florida Keys Beaches ...
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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!
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

Cudjoe Key
Book a stay at this family-friendly vacation home in Summerland Key. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Florida Keys Beaches ...
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
 Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Cudjoe Key
Book a stay at this beach vacation home in Summerland Key. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Florida Keys Beaches and Upper ...
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Ocean Front - Private 56' Dock

Ocean Front - Private 56' Dock

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, tennis courts, and a pool table. Popular attractions Florida Keys Beaches and Venture Key are ...
Ocean Front - Private 56' Dock
Lower Keys paradise

Lower Keys paradise

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy a pool table, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Venture ...
Lower Keys paradise
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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
277 Holiday Homes
Lowest Price
NZ$441
Highest Price
NZ$1,541
Popular accommodation
Old Florida Style, wrap around porch, boat basin for dockage, open water, Beachside @ Torchview Waterfront Retreat , 3 night minimum! Spectacular Ocean Views!, Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security, COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!, Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5, Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Ocean Front - Private 56' Dock , Lower Keys paradise

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$441 per night from 3 Mar to 4 Mar
NZ$441
includes taxes & fees
3 Mar - 4 Mar
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
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$469 per night from 3 Mar to 4 Mar
NZ$469
includes taxes & fees
3 Mar - 4 Mar
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
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
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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$488 per night from 2 Mar to 3 Mar
NZ$488
includes taxes & fees
2 Mar - 3 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.