Book Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key

 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$678 per night from 29 May to 30 May
AU$678
per night
29 May - 30 May
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
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
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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 Key.
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification

WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification

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.
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
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
Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
The price is AU$840 per night from 9 May to 10 May
AU$840
per night
9 May - 10 May
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
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
With a stay at this vacation home in Summerland Key, you'll be on the beach, just a 4-minute walk from Florida Keys Beaches and within a 5-minute drive of Crab ...
One of the very few beach houses with a daily, rental license in the Keys.
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
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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
231 Holiday Homes
Lowest Price
AU$259
Highest Price
AU$840
Popular accommodation
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, 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, Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West, WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification , Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5, Kelly's Kabin - Adorable Private Summerland Key Cottage, One of the very few beach houses with a daily, rental license in the Keys., Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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
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 5 May to 6 May
AU$289
per night
5 May - 6 May
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
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$259 per night from 15 May to 16 May
AU$259
per night
15 May - 16 May
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
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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$294 per night from 12 May to 13 May
AU$294
per night
12 May - 13 May
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
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.