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Top Holiday Rentals in Summerland Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.0 out of 10, Wonderful, (6)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is £467
includes taxes & fees
22 Jul - 23 Jul
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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

8.8 out of 10, Excellent, (85)
"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 £522
includes taxes & fees
20 Jul - 21 Jul
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (117)
"This was our second time staying here. Feels very secluded although it's right off the highway. We saw many Key deer on our way to No Name Pub , including babies who thougt we should feed them) (We did not feed them). Highly recommend!"
The price is £372
includes taxes & fees
20 Jul - 21 Jul
Kelly's Kabin - Adorable Private Summerland Key Cottage

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (80)
"Great atmosphere, right on a canal. A perfect and comfortable home!"
The price is £422
includes taxes & fees
2 Aug - 3 Aug
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (5)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is £467
includes taxes & fees
20 Jul - 21 Jul
Island Time #110 Ocean Views - Cudjoe Key

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very good, (114)
"Great place to get away. House and property were nice. If your bring a boat, you have to watch the tides. Flats or a smaller bay boat will be fine. Had a 21 foot center console. Low tide you just have to take it slow out to the channel. Great options for docking your boat. A lot of space for boat trailers. Location of property is nicely situated. "
The price is £409
includes taxes & fees
2 Aug - 3 Aug
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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."
The price is £387
includes taxes & fees
22 Jul - 23 Jul
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

10.0 out of 10, Exceptional, (1)
"We just needed a place to sleep for a few days while visiting friends on Big Pine. The house had what we needed. The home and furnishings were quite dated with some rust stains on the air vents and in the bath but if you're not picky about that, then this is a great place. The main areas were clean, although there was dirt and dust behind the night stands (needed to access the outlet so had to look there). We didn't use any of the amenities but still had to pay 130 extra when we checked in at...
The price is £332
includes taxes & fees
5 Aug - 6 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Private and Exclusive Florida Keys Getaway

10.0 out of 10, Exceptional, (10)
"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"
Private and Exclusive Florida Keys Getaway

Sailfish Haven #390 - Ocean Views, 35' seawall

8.8 out of 10, Excellent, (6)
"We really enjoyed our stay. The home was exactly as advertised which we definitely appreciated. It was nice to have the kitchen with a wine opener and decent dishes. Being on the water was a plus for our cousin specifically but enjoyed by all. We sat on the back deck morning and night. It was fun to watch the pelicans and boats. Definitely highly recommend. "
The price is £492
includes taxes & fees
23 Jul - 24 Jul
Sailfish Haven #390 - Ocean Views, 35' seawall

Private and Exclusive Beach Getaway

10.0 out of 10, Exceptional, (10)
"I loved the secluded nature of the property it felt like we had the whole place to ourselves. Beach was beautiful and the property manager was very responsive. The location is close enough to Key West that it’s easy to do an excursion or go to dinner. "
The price is £1,308
includes taxes & fees
11 Aug - 12 Aug
Private and Exclusive Beach Getaway

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

9.8 out of 10, Exceptional, (235)
"We (family of 5) really enjoyed our stay. All the equipment was as listed and in great condition. The location was perfect if you're looking for a less hectic Florida Keys experience."
The price is £666
includes taxes & fees
25 Jul - 26 Jul
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (96)
"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."
The price is £405
includes taxes & fees
23 Jul - 24 Jul
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

The Lighthouse - Beach Houses Key West

9.6 out of 10, Exceptional, (11)
"We saved up for 3 years for this trip and this property did not disappoint! Thank you for sharing your beautiful piece of paradise with us!"
The price is £1,206
includes taxes & fees
28 Jul - 29 Jul
The Lighthouse - Beach Houses Key West

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 £1,056
includes taxes & fees
12 Aug - 13 Aug
One of the very few beach houses with a daily, rental license in the Keys.

Private and Exclusive Beach Getaway

10.0 out of 10, Exceptional, (1)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
The price is £1,661
includes taxes & fees
6 Aug - 7 Aug
Private and Exclusive Beach Getaway

The Hemingway - Beach Houses Key West

9.8 out of 10, Exceptional, (7)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
The price is £914
includes taxes & fees
18 Jul - 19 Jul
The Hemingway - Beach Houses Key West

Spanish Queen @Venture Out, Cudjoe Key

9.4 out of 10, Exceptional, (18)
"We enjoyed our stay at venture out at the Spanish main residence it was lovely and we are going to return again next year"
The price is £518
includes taxes & fees
16 Jul - 17 Jul
Spanish Queen @Venture Out, Cudjoe Key

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

9.8 out of 10, Exceptional, (8)
"Great home base for fly fishing"
The price is £693
includes taxes & fees
25 Jul - 26 Jul
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
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?

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 JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community! and Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West.

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.