Summerland Key Vacation Rentals from ￥18,406: Search Short-Term Rentals

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Vacation Rentals in Summerland Key

"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "

￥102,744 total

includes taxes & fees

Aug 20 - Aug 21

"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."

"I will sum it up by saying it was ok. It was a place to stay, would I book it again? No"

"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "

￥101,727 total

includes taxes & fees

Aug 16 - Aug 17

"My husband and I stayed with our son in the cottage and it was everything we needed. Great location, beautiful pool on the water, and just enough space. "

"Good Fishing, Good local eateries. "

"We had an excellent time , property was an excellent place for our vacation.We hope to come back next year"

"Our stay was amazing, the house had EVERYTHING we needed for our trip. Perfect location, beautiful scenery. Just perfect "

"It was a beautiful home and Francine, our host, was most accommodating."

"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "

"The place was spacious, very clean and beautiful!"

￥92,694 total

includes taxes & fees

Aug 15 - Aug 16

"Everything was exactly as described, the host was gracious and communicative, the house is great for a large group and a quiet location"

"Great little spot, location was perfect, house was cozy, and the host was fantastic! The staff at Venture Out were also extremely courteous. Would definitely stay here again. "

"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "

"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "

￥37,401 total

includes taxes & fees

Aug 27 - Aug 28

"Beautiful place!"

￥120,811 total

includes taxes & fees

Aug 26 - Aug 27

"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "

￥46,887 total

includes taxes & fees

Aug 18 - Aug 19

"Nice place and susan was an excellent hosts "

"Our stay was perfect. The only complain was that we couldn’t stay longer. Walt gave us a great overview of the property available amenities. The short walk to Kiki’s Sandbar makes the stay extra enjoyable. Little Torch Key is the perfect spot to avoid the hustle and bustle of Key West, but remains convenient to all of the Keys activities. "

"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."

￥87,561 total

includes taxes & fees

Aug 21 - Aug 22

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Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Beautifully landscaped grounds, clean amenities, something for everyone "

Parmer's Resort

10/10 Excellent

"This is a beautiful place, a hidden treasure. The breakfast was plentiful with fresh breads, fresh fruit, a variety of cereals, and good hot coffee. The staff was very friendly, helpful, and accommodating. If you have limited mobility, pay attention when you book to make sure you can access the room you are booking. You can call the hotel direct and they will help you. A great place to stay. "

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

10/10 Excellent

"The cottage was perfect for me and my 3 kids. We loved the location being less than a 30min drive from both Key West and Marathon, and within 20min of several beaches. The kids took a dip in the private pool in the back everyday. Check-in process was seamless, and the rooms were perfectly climate controlled. We'll definitely stay again next time we're in the keys."

One of the very few beach houses with a daily, rental license in the Keys.

10/10 Excellent

"My family and I had an incredible stay. We utilized every available component of the home including the dock. Property manager provided us with 2 available free ramps to drop off our jet-skis. We settled on the ramp located on Blimp Road, which was a 10 minute drive and 15-20 minute ride on the skis. We were able to tie off our skis our whole stay with no issues. Home was exactly as disclosed and worked great for our family. Communication was great, with quick respond time. "

Find out more about Summerland Key

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Frequently asked questions

Can I find vacation rentals in Summerland Key?

Yes, you can find vacation rentals close to top local attractions in Summerland Key, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Summerland Key?

Old Florida Style, wrap around porch, boat basin for dockage, open water: This Summerland Key vacation home rental is located by the ocean and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. Some other top choices in Summerland Key are Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West and Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!.

How many vacation rentals are there in Summerland Key?

Choose from 483 Expedia vacation rentals in Summerland Key for a memorable vacation.

What can I see and do in Summerland Key?

Florida Keys Beaches and Sugarloaf Beach are a couple of lovely local spots to get outside and enjoy nature. Venture Out Keys and Upper Sugarloaf Key are other places to visit while you're in town.

What are vacation rentals like in Summerland Key?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Summerland Key. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.

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Summerland Key Vacation Rentals

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Vacation Rentals in Summerland Key

Old Florida Style, wrap around porch, boat basin for dockage, open water

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Canal front, dockage, 2 bedroom, 2 bath

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Dockage, just minutes to Key West

Quaint cottage, pool, dockage just minutes to Key West!

Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

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

Direct Oceanfront Cottage-Sunrise View- #2,

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

Private Secluded Ocean View & Pool Near Key West

20 MINUTES TO KEY WEST , BOATERS PARADISE

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Boat Dockage just minutes to Key West!

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Charming cottages, dockage, pool, just minutes to Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Waterfront Anchor House with Boat Basin & Ramp!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Parmer's Resort

Private Secluded Ocean View & Pool Near Key West

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Sugar Loaf Lodge

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Direct Oceanfront Cottage-Sunrise View- #2,

One of the very few beach houses with a daily, rental license in the Keys.

Cottage with swimming pool and dockage, just minutes to Key West!

Find out more about Summerland Key

Frequently asked questions