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
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
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
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 Key.
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

LICENSE TO CHILL ~ 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 10-minute drive of Florida Keys Beaches and Venture Key.
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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Cozy, Perfect Conch Cottage!

Cozy, Perfect Conch Cottage!

Cudjoe Key
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 Venture Key.
Cozy, Perfect Conch Cottage!
Just 20 miles from Key West!  Oceanfront, dockage, swimming pool

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

Cudjoe Key
With a stay at this vacation home in Summerland Key (Cutthroat Harbor Estates), you'll be within a 10-minute drive of Florida Keys Beaches and Venture Key.
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
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 Key.
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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
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.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
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
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 Key.
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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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
AU$272
Highest Price
AU$289
Popular accommodation
Old Florida Style, wrap around porch, boat basin for dockage, open water, Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!, Cozy, Perfect Conch Cottage!, Just 20 miles from Key West! Oceanfront, dockage, swimming pool, Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security, Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Beachside @ Torchview Waterfront Retreat , COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Top trending hotels in Summerland Key

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

2 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
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$272 per night from 16 Jun to 17 Jun
AU$272
per night
16 Jun - 17 Jun
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$289 per night from 10 Jun to 11 Jun
AU$289
per night
10 Jun - 11 Jun
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
Save an average of 15% on thousands of hotels when you're signed in
Little Palm Island Resort & Spa - A Noble House Resort

Little Palm Island Resort & Spa - A Noble House Resort

4.5 out of 5
28500 Overseas Hwy, Summerland Key, FL
With a stay at Little Palm Island Resort & Spa - A Noble House Resort in Summerland Key, you'll be by the ocean, within a 15-minute drive of Florida Keys Beaches ...
Little Palm Island Resort & Spa - A Noble House 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.