Book Holiday Homes in Summerland Key

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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 FL
The price is NZ$1,413 per night from 21 Apr to 22 Apr
NZ$1,413
21 Apr - 22 Apr
includes taxes & fees
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Opens in a new windowOceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

Summerland Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowPrivate Secluded Ocean View & Pool Near Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key FL
The price is NZ$1,196 per night from 5 Apr to 6 Apr
NZ$1,196
5 Apr - 6 Apr
includes taxes & fees
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Opens in a new windowCudjoe Cottages, swimming pool, just 20 miles from Key West
Save an average of 15% on thousands of hotels when you're signed in
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 FL
The price is NZ$1,120 per night from 25 Mar to 26 Mar
NZ$1,120
25 Mar - 26 Mar
includes taxes & fees
Stay at this holiday home in Summerland Key. Enjoy a garden, laundry facilities and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
Opens in a new windowDirect 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 FL
Stay at this holiday home in Summerland Key. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Big Pine Key Flea Market and ...
Opens in a new windowOld Florida Style, wrap around porch, boat basin for dockage, open water
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 FL
Stay at this family-friendly holiday home in Summerland Key. Enjoy free Wi-Fi, 2 outdoor pickleball courts and laundry facilities. Popular attractions Florida ...
Opens in a new windowOceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Open water views! Golf cart included!  Beautiful 2 bedroom house in Venture Out

Open water views! Golf cart included! Beautiful 2 bedroom house in Venture Out

Cudjoe Key FL
Stay at this family-friendly holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions Florida Keys Beaches ...
Opens in a new windowOpen water views! Golf cart included! Beautiful 2 bedroom house in Venture Out
Sunny Hideaway - Venture Out Unit 276

Sunny Hideaway - Venture Out Unit 276

Summerland Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and cable/satellite TV service. Popular attractions Florida Keys Beaches and ...
Opens in a new windowSunny Hideaway - Venture Out Unit 276
Beachside @ Torchview Waterfront Retreat

Beachside @ Torchview Waterfront Retreat

Summerland Key FL
Stay at this beach holiday home in Summerland Key. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Blue Hole and Crab Key are located ...
Opens in a new windowBeachside @ Torchview Waterfront Retreat
Don't see what you're looking for?
See all available properties in Summerland Key
View all properties
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
411 Holiday Homes
Lowest Price
NZ$401
Highest Price
NZ$1,413
Popular accommodation
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West, Private Secluded Ocean View & Pool Near Key West, Cudjoe Cottages, swimming pool, just 20 miles from Key West, 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, Open water views! Golf cart included! Beautiful 2 bedroom house in Venture Out , Sunny Hideaway - Venture Out Unit 276, Beachside @ Torchview Waterfront Retreat

Top trending hotels in Summerland Key

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 hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSugarloaf 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 NZ$401 per night from 29 Mar to 30 Mar
NZ$401
29 Mar - 30 Mar
includes taxes & fees
Stay at this beach motel in Summerland Key. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
Opens in a new windowParmer's 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
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowLooe Key Reef Resort
Save an average of 15% on thousands of hotels when you're signed in
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$480 per night from 23 Mar to 24 Mar
NZ$480
23 Mar - 24 Mar
includes taxes & fees
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a marina. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSugar Loaf Lodge
Don't see what you're looking for?
See all available properties in Summerland Key
View all properties
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.