Holiday Rentals in Summerland Key

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Holiday Rentals in Summerland Key

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

9.6 out of 10, Exceptional, (77)
"Took the team down to the keys for a little R&R"
The price is €614
includes taxes & fees
20 Aug - 21 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

9.0 out of 10, Wonderful, (85)
"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. "
The price is €306
includes taxes & fees
20 Aug - 21 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (85)
"I will sum it up by saying it was ok. It was a place to stay, would I book it again? No"
Canal front, dockage, 2 bedroom, 2 bath

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

8.8 out of 10, Excellent, (86)
"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. "
The price is €604
includes taxes & fees
20 Aug - 21 Aug
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (189)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (152)
"Good Fishing, Good local eateries. "
Cottage with Pool and Dockage, just minutes to Key West

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

9.8 out of 10, Exceptional, (73)
"We loved the spacious home with pool and little fishing dock. The kayaks were fun too. It was roughly 30 minutes to key west and the same to marathon key. Would definitely stay again."
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

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

8.6 out of 10, Excellent, (144)
"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. "
The price is €223
includes taxes & fees
27 Aug - 28 Aug
Cottage with Pool and Boat Dockage just minutes to Key West!

Springs Venture Out Dolphin House (#386) with beautiful open water views

9.2 out of 10, Wonderful, (100)
"We absolutely loved our time here! GORGEOUS view of the bay! It was exactly what we needed for our guys trip!"
Springs Venture Out Dolphin House (#386) with beautiful open water views

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

8.8 out of 10, Excellent, (162)
"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."
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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

9.8 out of 10, Exceptional, (8)
"Beautiful place!"
The price is €719
includes taxes & fees
31 Aug - 1 Sept
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

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

8.6 out of 10, Excellent, (119)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
The price is €289
includes taxes & fees
20 Aug - 21 Aug
Charming cottages, dockage, pool, just minutes to Key West

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

9.0 out of 10, Wonderful, (151)
"The place was spacious, very clean and beautiful!"
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

7.8 out of 10, Good, (12)
"Good experience. The property is well place and the Venture is really nice and quiet."
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Mini lobster available! Open Water View from porch , dock, bikes, kayaks

9.8 out of 10, Exceptional, (121)
"We loved having our own space for a boat. Great location."
Mini lobster available! Open Water View from porch , dock, bikes, kayaks

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

9.8 out of 10, Exceptional, (236)
"Clean and inviting property, great location, attentive host. Highly recommend."
The price is €717
includes taxes & fees
31 Aug - 1 Sept
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

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

8.8 out of 10, Excellent, (145)
"Near to Key West in a quiet neighborhood. "
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

9.0 out of 10, Wonderful, (153)
"The cottage was comfortable, and the bed was just right. We were in the Keys for a funeral, so not much running around."
Cottage with swimming pool and dockage, just minutes to Key West!

Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!

2.5 star property
10.0 out of 10, Exceptional, (5)
"Our stay was wonderful! The view is amazing, the home was clean and very well stocked. We had a wonderful time."
Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!

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

8.8 out of 10, Excellent, (64)
"The house is special, it transmits a lot of peace next to that spectacular dock where the fishing is fabulous, everything is very clean and well equipped with cauldrons etc.I will be back 100%"
The price is €1,154
includes taxes & fees
25 Aug - 26 Aug
One of the very few beach houses with a daily, rental license in the Keys.
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.
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Top Summerland Key Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Summerland Key?

Yes, there are holiday rentals close to the most popular sights in Summerland Key, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Summerland Key has to offer?

Old Florida Style, wrap around porch, boat basin for dockage, open water: This highly rated holiday home rental in Summerland Key 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 that 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 holiday rentals are there in Summerland Key?

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

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 holiday rentals like in Summerland Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Summerland Key. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.