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Browse Select Summerland Key Holiday Homes

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

9.6 out of 10, Exceptional, (96)
"Good location, short drive to lots of activities. Had to leave a day early due to family crises, but had a great two nights there. Thanks!!"
The price is £330
includes taxes & fees
28 Aug - 29 Aug
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is £448
includes taxes & fees
20 Aug - 21 Aug
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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

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

9.8 out of 10, Exceptional, (81)
"Great location near Key West. Awesome property, will book again."
The price is £358
includes taxes & fees
20 Aug - 21 Aug
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

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 £518
includes taxes & fees
16 Aug - 17 Aug
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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 £616
includes taxes & fees
20 Aug - 21 Aug
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (7)
"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 £468
includes taxes & fees
19 Aug - 20 Aug
Island Time #110 Ocean Views - Cudjoe Key

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 £344
includes taxes & fees
29 Aug - 30 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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 £942
includes taxes & fees
25 Aug - 26 Aug
One of the very few beach houses with a daily, rental license in the Keys.

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 £442
includes taxes & fees
2 Sept - 3 Sept
Sailfish Haven #390 - Ocean Views, 35' seawall

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (118)
"Clean property in a nice location."
The price is £393
includes taxes & fees
2 Sept - 3 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
8.8 out of 10, Excellent, (6)
The price is £470
includes taxes & fees
2 Sept - 3 Sept
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

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

9.8 out of 10, Exceptional, (8)
"Beautiful place!"
The price is £618
includes taxes & fees
22 Aug - 23 Aug
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

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 £1,447
includes taxes & fees
31 Aug - 1 Sept
Private and Exclusive Beach Getaway

Reel Island Retreat #273 at Venture Out in the Florida Keys

9.6 out of 10, Exceptional, (7)
"The staff at Venture one was absolutely amazing. The home we stayed in was also a great location. Dated but clean. Definitely will stay at Venture again !"
The price is £468
includes taxes & fees
2 Sept - 3 Sept
Reel Island Retreat #273 at Venture Out in the Florida Keys

Galleon Getaway #533- Oceanfront Community

The price is £408
includes taxes & fees
20 Aug - 21 Aug
Galleon Getaway #533- Oceanfront Community

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

9.4 out of 10, Exceptional, (26)
"Close to Key West and lots of great boating"
The price is £470
includes taxes & fees
2 Sept - 3 Sept
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

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

9.6 out of 10, Exceptional, (77)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is £525
includes taxes & fees
20 Aug - 21 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water

Mahi House #440 - 35' seawall

10.0 out of 10, Exceptional, (1)
"The house was just right. Nice community. Quiet and peaceful. Just what we needed. The host was kind and responsive. "
The price is £463
includes taxes & fees
2 Sept - 3 Sept
Mahi House #440 - 35' seawall

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 £515
includes taxes & fees
20 Aug - 21 Aug
Spanish Queen @Venture Out, Cudjoe Key
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