Book Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Florida Keys Beaches and Venture ...
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Key
The price is NZ$1,023 per night from 3 Aug to 4 Aug
NZ$1,023
3 Aug - 4 Aug
includes taxes & fees
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Big Pine Key Flea Market ...
Old Florida Style, wrap around porch, boat basin for dockage, open water
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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, laundry facilities, and tennis courts. Popular attractions Florida Keys ...
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
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Summerland Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Blue Hole and Crab Key are located ...
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
20 MINUTES TO KEY WEST , BOATERS PARADISE

20 MINUTES TO KEY WEST , BOATERS PARADISE

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and a pool table. Our guests praise the helpful staff in our reviews. Popular ...
20 MINUTES TO KEY WEST , BOATERS PARADISE
Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

Summerland Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
Private Secluded Ocean View & Pool Near Key West
Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key

2.5 out of 5
Cudjoe Key
The price is NZ$1,050 per night from 2 Sept to 3 Sept
NZ$1,050
2 Sept - 3 Sept
includes taxes & fees
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and tennis courts. Popular attractions Florida Keys Beaches and Venture Key ...
Island Time #110 Ocean Views - Cudjoe 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.

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
376 Holiday Homes
Lowest Price
NZ$188
Highest Price
NZ$1,050
Popular accommodation
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, Old Florida Style, wrap around porch, boat basin for dockage, open water, Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security, Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel , 20 MINUTES TO KEY WEST , BOATERS PARADISE, Private Secluded Ocean View & Pool Near Key West, Island Time #110 Ocean Views - Cudjoe Key

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 NZ$286 per night from 26 Aug to 27 Aug
NZ$286
26 Aug - 27 Aug
includes taxes & fees
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
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$188 per night from 10 Aug to 11 Aug
NZ$188
10 Aug - 11 Aug
includes taxes & fees
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
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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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$359 per night from 11 Aug to 12 Aug
NZ$359
11 Aug - 12 Aug
includes taxes & fees
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
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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.