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 AU$1,433 per night from 2 Feb to 3 Feb
AU$1,433
includes taxes & fees
2 Feb - 3 Feb
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 ...
Old Florida Style, wrap around porch, boat basin for dockage, open water
Beachside @ Torchview Waterfront Retreat

Beachside @ Torchview Waterfront Retreat

Summerland Key
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 ...
Beachside @ Torchview Waterfront Retreat
3 night minimum! Spectacular Ocean Views!

3 night minimum! Spectacular Ocean Views!

Cudjoe Key
With a stay at this vacation home in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
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
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: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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
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.
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
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
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 15-minute drive of Florida Keys Beaches and Venture Out Keys.
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
 Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

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

Cudjoe Key
The price is AU$1,459 per night from 20 Feb to 21 Feb
AU$1,459
includes taxes & fees
20 Feb - 21 Feb
With a stay at this vacation home in Summerland Key, you'll be on the beach, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Lower Keys paradise

Lower Keys paradise

Cudjoe Key
With a stay at this vacation home in Summerland Key, you'll be by the ocean, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Lower Keys paradise
Ocean Front - Private 56' Dock

Ocean Front - Private 56' Dock

Cudjoe Key
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 Key.
Ocean Front - Private 56' Dock
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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
273 Holiday Homes
Lowest Price
AU$311
Highest Price
AU$1,459
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, Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5, COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!, Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Lower Keys paradise, Ocean Front - Private 56' Dock

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 AU$311 per night from 23 Jan to 24 Jan
AU$311
includes taxes & fees
23 Jan - 24 Jan
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 ...
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 AU$347 per night from 23 Jan to 24 Jan
AU$347
includes taxes & fees
23 Jan - 24 Jan
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 ...
Parmer's Resort
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 AU$356 per night from 23 Jan to 24 Jan
AU$356
includes taxes & fees
23 Jan - 24 Jan
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.
Sugar Loaf Lodge
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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 ...
Sugarloaf Key Hotel at KOA Resort
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.

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^Subject to availability and chosen travel dates.