Book Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key

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
Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
The price is AU$946 per night from 1 Dec to 2 Dec
AU$946
includes taxes & fees
1 Dec - 2 Dec
With a stay at this vacation home in Summerland Key, you'll be within a 5-minute drive of Florida Keys Beaches and Crab Key.
Kelly's Kabin - Adorable Private Summerland Key Cottage
20 MINUTES TO KEY WEST , BOATERS PARADISE

20 MINUTES TO KEY WEST , BOATERS PARADISE

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.
20 MINUTES TO KEY WEST , BOATERS PARADISE
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WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

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.
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
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!
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to 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 Venture Out Keys.
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
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 Out ...
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Walk to  Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

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.
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Latitudes - Ocean front with pool

Latitudes - Ocean front with pool

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 Upper Sugarloaf Key.
Latitudes - Ocean front with pool
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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
283 Holiday Homes
Lowest Price
AU$207
Highest Price
AU$946
Popular accommodation
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Kelly's Kabin - Adorable Private Summerland Key Cottage, 20 MINUTES TO KEY WEST , BOATERS PARADISE, WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS, COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!, Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West, Just 20 miles from Key West! Oceanfront, dockage, swimming pool, Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear, Latitudes - Ocean front with pool

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$284 per night from 18 Nov to 19 Nov
AU$284
includes taxes & fees
18 Nov - 19 Nov
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
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
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$211 per night from 18 Nov to 19 Nov
AU$211
includes taxes & fees
18 Nov - 19 Nov
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
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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 AU$207 per night from 1 Dec to 2 Dec
AU$207
includes taxes & fees
1 Dec - 2 Dec
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
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.