Search Vacation Homes in Sugarloaf Key

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Vacation Homes in Sugarloaf Key

Palm - Beach Houses Key West

Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"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!"
United States
Crystal G.
$1,390 nightly
The price is $1,530
Nov 19 - Nov 20
Total with taxes and fees
Palm - Beach Houses Key West

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

Sands
$509 nightly
The price is $565
Nov 11 - Nov 12
Total with taxes and fees
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.
$393 nightly
The price is $436
Nov 9 - Nov 10
Total with taxes and fees
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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.
$473 nightly
The price is $525
Nov 9 - Nov 10
Total with taxes and fees
NOV. & DEC. 50% OFF! OCEANFRONT, 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.
$621 nightly
The price is $690
Nov 19 - Nov 20
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water

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
$536 nightly
The price is $595
Nov 9 - Nov 10
Total with taxes and fees
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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.
$558 nightly
The price is $619
Nov 12 - Nov 13
Total with taxes and fees
Island Time #110 Ocean Views - 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.
$516 nightly
The price is $573
Nov 20 - Nov 21
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage

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.
$1,186 nightly
The price is $1,316
Nov 11 - Nov 12
Total with taxes and fees
One of the very few beach houses with a daily, rental license in the Keys.

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.
$560 nightly
The price is $621
Nov 9 - Nov 10
Total with taxes and fees
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)
"Deer in the front yard, perfect location, clean and friendly "
United States
Sara H.
$483 nightly
The price is $536
Nov 10 - Nov 11
Total with taxes and fees
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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.
$613 nightly
The price is $681
Nov 10 - Nov 11
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

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

2.0 star property
Cudjoe Key
$530 nightly
The price is $588
Nov 9 - Nov 10
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

2.0 star property
Cudjoe Key
$552 nightly
The price is $613
Nov 9 - Nov 10
Total with taxes and fees
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

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.
$429 nightly
The price is $476
Nov 30 - Dec 1
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely 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.
$650 nightly
The price is $721
Nov 9 - Nov 10
Total with taxes and fees
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

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

2.0 star property
Cudjoe Key
$601 nightly
The price is $668
Nov 10 - Nov 11
Total with taxes and fees
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront Luxury Home - Tidelands House

2.0 star property
Raccoon Key
$2,244 nightly
The price is $2,525
Nov 11 - Nov 12
Total with taxes and fees
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.
$819 nightly
The price is $909
Nov 10 - Nov 11
Total with taxes and fees
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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