Holiday Homes in Sugarloaf Key

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Featured Holiday Homes in Sugarloaf Key

Palm - Beach Houses Key West

Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"Excellent place to stay if you are seeking a getaway off the beaten path. Well landscaped to give privacy to each bungalow. 2 amazing piers to fish/jet ski from. The pool and grill area is a PERFECT place to cool off and escape the heat with the swim up bar. The staff even gave us coconuts to enjoy fresh from their trees. Each day we saw amazing wildlife and even had key deer visit us. We are considering booking the whole place for a family reunion. Would also make for a great corporate...
United States
Robert K.
Palm - Beach Houses Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Sands
The price is NZ$1,010
includes taxes & fees
12 Nov - 13 Nov
Charming 3-bedroom house in Big Pine Key near Beach and Key West

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.6 out of 10, Exceptional, (98)
"This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. "
United States
Edward H.
The price is NZ$767
includes taxes & fees
17 Nov - 18 Nov
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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

Little Torch Key
9.6 out of 10, Exceptional, (84)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
United States
Kendra K.
The price is NZ$1,222
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water

NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"Great property, owners were very helpful and we really enjoyed our stay!"
United States
Lee J.
The price is NZ$932
includes taxes & fees
16 Nov - 17 Nov
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
Cudjoe Key
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
United States
Javier
The price is NZ$1,052
includes taxes & fees
15 Nov - 16 Nov
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (119)
"Great location for some much needed time away."
United States
Brad R.
The price is NZ$1,019
includes taxes & fees
20 Nov - 21 Nov
Kelly's Kabin - Adorable Private Summerland Key Cottage

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
Cudjoe Key
9.4 out of 10, Exceptional, (10)
"Greta property, really enjoyed the water view and the bbq grill "
United States
William B.
The price is NZ$1,092
includes taxes & fees
17 Nov - 18 Nov
Island Time #110 Ocean Views - Cudjoe Key

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

Cudjoe Key
9.6 out of 10, Exceptional, (7)
"Very clean place"
United States
Michael T.
The price is NZ$1,097
includes taxes & fees
14 Nov - 15 Nov
Reel Island Retreat #273 at Venture Out in the Florida Keys

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

Cutthroat Harbor Estates
8.4 out of 10, Very good, (117)
"The whole experience was decent until the last night. We met with a lot of termites and two cockroaches"
United States
Kiril
The price is NZ$955
includes taxes & fees
18 Nov - 19 Nov
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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

Summerland Key
8.8 out of 10, Excellent, (64)
"We had a wonderful stay. The house was so inviting and the view was spectacular. I would strongly suggest that some work be done in the kitchen. Frying pans were warped, counter oven had a sprung door, toaster only worked on one side. Also, the bunk beds needed tightening. They were a little scary. Yes, I would go back again. "
United States
Meredith A.
The price is NZ$2,340
includes taxes & fees
12 Nov - 13 Nov
One of the very few beach houses with a daily, rental license in the Keys.

Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Key
9.4 out of 10, Exceptional, (19)
"This home was perfect for our family of four to enjoy a few days in paradise. The amenities provided were amazing and the home was beautiful. The host was very easy to contact and attentive to any questions we had. We will definitely be back again and highly recommend this property."
United States
Mandy M.
The price is NZ$1,204
includes taxes & fees
17 Nov - 18 Nov
Spanish Queen @Venture Out, Cudjoe Key

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

Cudjoe Key
10.0 out of 10, Exceptional, (2)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

2.0 star property
Cudjoe Key
The price is NZ$1,036
includes taxes & fees
22 Nov - 23 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

2.0 star property
Cudjoe Key
The price is NZ$1,188
includes taxes & fees
24 Nov - 25 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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

Cudjoe Key
9.4 out of 10, Exceptional, (27)
"Lovely property by the water in Cudjoe Key. Very comfortable and well equipped. Host was very communicative and location was great for getting to Key West and other local attractions. Would definitely stay again! "
United Kingdom
Tom K.
The price is NZ$1,260
includes taxes & fees
24 Nov - 25 Nov
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Waterfront Luxury Home - Tidelands House

2.0 star property
Raccoon Key
The price is NZ$5,381
includes taxes & fees
18 Nov - 19 Nov
Waterfront Luxury Home - Tidelands House

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

Cudjoe Key
9.8 out of 10, Exceptional, (10)
"Beautiful place!"
United States
Sara C.
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Cudjoe Key
10.0 out of 10, Exceptional, (2)
"Super spot and views of the Straits. Very clean with new modern appliances and amenities. Comfortable and relaxing. Roku TVs make it a challenge to watch major sporting events, but that’s not why we were there. Pool spa out of service due to “health concerns,” but the pool itself seemed ok. Overall, a peaceful and calm stay all about the soothing views with only the splashing sounds of the occasional fish chasing bait. "
United States
Anonymous traveller
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Larkshine House at Lunara Bay

2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (6)
"Great property and great management. Our trip could not have gone any better"
United States
William G.
The price is NZ$4,601
includes taxes & fees
10 Dec - 11 Dec
Larkshine House at Lunara Bay
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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