Sugarloaf Key Holiday Rentals

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Check prices for these dates

Tonight
14 Nov - 15 Nov
Tomorrow
15 Nov - 16 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Sugarloaf Key

Pool
Palm - Beach Houses Key West

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.
The price is HK$5,983
HK$12,270 total
includes taxes & fees
19 Nov - 20 Nov
Palm - Beach Houses Key West
Beach nearby
Hammock House - Beach Houses Key West

Hammock House - Beach Houses Key West

Sugarloaf Key
8.0 out of 10, Very good, (2)
"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 "
United States
Samat S.
The price is HK$13,676
HK$22,671 total
includes taxes & fees
24 Nov - 25 Nov
Hammock House - Beach Houses Key West
Pool
Azucar - Beach Houses Key West

Azucar - Beach Houses Key West

Sugarloaf Key
10.0 out of 10, Exceptional, (10)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
The price is HK$10,685
HK$18,509 total
includes taxes & fees
10 Dec - 11 Dec
Azucar - Beach Houses Key West
Restaurant
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is HK$864
HK$2,274 total
includes taxes & fees
16 Nov - 17 Nov
Aqua Lodges at Hurricane Hole Marina
Kayaking
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (158)
"Todo perfect"
Mexico
Rachel
The price is HK$2,992
HK$3,366 total
includes taxes & fees
12 Dec - 13 Dec
Sunshine Key RV Resort & Marina
Outdoor pool
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is HK$1,943
HK$3,893 total
includes taxes & fees
16 Nov - 17 Nov
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Living area
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (271)
"We will definitely stay here again. Perfect spot to relax. Clean Rooms "
United States
Gregory
Old Wooden Bridge Resort and Marina
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Cudjoe Key
8.2 out of 10, Very good, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
The price is HK$1,049
HK$2,465 total
includes taxes & fees
30 Nov - 1 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Pool
Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (158)
"Great location and very happy with our accommodations."
United States
Carrie B.
The price is HK$1,166
HK$2,465 total
includes taxes & fees
16 Nov - 17 Nov
Cottage with Pool and Dockage, just minutes to Key West
Outdoor dining
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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 HK$1,158
HK$3,365 total
includes taxes & fees
17 Nov - 18 Nov
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key
9.0 out of 10, Wonderful, (88)
"Community is great, location in the Keys is great, house was perfect for our family of 3."
United States
Christina H.
The price is HK$1,360
HK$3,044 total
includes taxes & fees
16 Nov - 17 Nov
Canal front, dockage, 2 bedroom, 2 bath
Fridge, microwave, oven, stovetop
Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (120)
"Great location for some much needed time away."
United States
Brad R.
The price is HK$1,748
HK$4,202 total
includes taxes & fees
20 Nov - 21 Nov
Kelly's Kabin - Adorable Private Summerland Key Cottage
A heated pool
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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 HK$1,469
HK$4,613 total
includes taxes & fees
16 Nov - 17 Nov
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very good, (315)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is HK$1,791
HK$2,278 total
includes taxes & fees
17 Nov - 18 Nov
Hyatt Vacation Club at Sunset Harbor, Key West
Outdoor pool, a heated pool
NOV. & DEC. 50% OFF! OCEANFRONT, 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.
The price is HK$1,702
HK$4,070 total
includes taxes & fees
16 Nov - 17 Nov
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Smart TV, books
Charming 3-bedroom house in Big Pine Key near Beach and Key West

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

Sands
The price is HK$1,935
HK$4,946 total
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

Little Torch Key
9.6 out of 10, Exceptional, (85)
"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 HK$2,331
HK$5,422 total
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water
Terrace/patio
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Old Town Key West
9.6 out of 10, Exceptional, (29)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
United States
Dianna F.
The price is HK$1,041
HK$2,959 total
includes taxes & fees
16 Nov - 17 Nov
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Property grounds
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Cudjoe Key
9.8 out of 10, Exceptional, (26)
"Renting was easy and hassle free."
United States
chuck s.
The price is HK$2,207
HK$4,743 total
includes taxes & fees
16 Nov - 17 Nov
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz
Marina
Living the Dream Key West Style

Living the Dream Key West Style

Stock Island
10.0 out of 10, Exceptional, (31)
"Clean rooms pet friendly great view! Exactly as advertised "
United States
Todd
The price is HK$2,091
HK$2,656 total
includes taxes & fees
17 Nov - 18 Nov
Living the Dream Key West Style
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 Sugarloaf Key Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Great setting and overall experience. Beautiful grounds!"
Michael 2-night trip
Posted 3 days ago
Winslow's Bungalows - Key West Historic Inns

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