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Top Holiday Rentals in Summerland Key

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

9.0 out of 10, Wonderful, (81)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
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)
"Excellent appearance, location, amenities and comfort. Bedrooms are a little tight but manageable. Host was very responsive and easy to work with. "
The price is £319
includes taxes & fees
28 Jun - 29 Jun
Canal front, dockage, 2 bedroom, 2 bath

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

9.6 out of 10, Exceptional, (75)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is £676
includes taxes & fees
27 Jun - 28 Jun
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, (49)
"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (223)
"We loved our stay here! This place had everything that we needed. The resort was safe for my kids to roam around for pickleball, swimming, and fishing. Thank you!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (146)
"Clean cottage, very helpful host, comfortable beds, great location --enjoyable stay."
Cottage with Pool and Dockage, just minutes to Key West

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

9.6 out of 10, Exceptional, (52)
"It was a beautiful home and Francine, our host, was most accommodating."
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Waterfront Home

8.8 out of 10, Excellent, (164)
"Property was perfect for our needs and a short distance from Key West. "
Waterfront Home

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (183)
"Great location on open water, good accommodations we enjoyed our stay, host was very helpful. Definitely returning. "
Direct Oceanfront Cottage-Sunrise View- #2,

Private Secluded Ocean View & Pool Near Key West

8.2 out of 10, Very good, (92)
"Property was as advertised "
Private Secluded Ocean View & Pool Near Key West

Fandango - private pool

9.8 out of 10, Exceptional, (78)
"My family and I had a great time staying at Fandago. It was located close enough to Key West to visit, yet far enough away to enjoy some privacy and peace and quiet. We were there for my daughter's wedding and everything was absolutely perfect! Would definitely stay again!"
Fandango - private pool

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

8.8 out of 10, Excellent, (83)
"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 £603
includes taxes & fees
15 Jul - 16 Jul
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

9.6 out of 10, Exceptional, (51)
"We really had a great time at this place! Perfect location and loved having the small kitchen."
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

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

9.8 out of 10, Exceptional, (7)
"Venture Out is a gated community in Cudjoe Key. The house was very clean and had everything you need to make yourself comfortable. We visited Key West which is about 30 minutes by car. Great place to stay"
The price is £619
includes taxes & fees
23 Jun - 24 Jun
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

FLAMINGO COTTAGE - Summer vacation Lobster and Fishing season- sleeps 4

9.8 out of 10, Exceptional, (43)
"We absolutely loved our stay here, it was perfect! "
FLAMINGO COTTAGE - Summer vacation Lobster and Fishing season- sleeps 4

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (247)
"Clean, easy access, friendly complex/neighborhood. "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

9.4 out of 10, Exceptional, (26)
"The cottage was perfect for my husband and I! It was very clean and quaint, definitely planning to stay again!!"
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

Oasis - Ocean view with pool and hot tub

9.0 out of 10, Wonderful, (27)
"To have my family under one roof for one week is amazing! The house was spacious, the outdoor decks, pool, kayaks, dock, and large kitchen/living room/dining space was perfect! "
Oasis - Ocean view with pool and hot tub

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

9.8 out of 10, Exceptional, (119)
"Spent a wonderful week here with our teen daughter. Loved having the option of riding bikes down to the pool. The location was perfect, right between Key West and Marathon Key. We found fun adventures within a short drive each day. Also enjoyed getting to know other people who were staying in the gated community resort! We’d love to come back!"
Mini lobster available! Open Water View from porch , dock, bikes, kayaks

Lower Keys paradise

10.0 out of 10, Exceptional, (33)
"The property was very clean and comfortable. We had a great stay "
Lower Keys paradise
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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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?

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill: This highly rated holiday home rental in Summerland Key is located near the beach, and has a balcony, a pool table and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind. Some other top choices in Summerland Key are Old Florida Style, wrap around porch, boat basin for dockage, open water and Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel .

How many holiday rentals are there in Summerland Key?

Choose from 475 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.