Holiday Homes in Sugarloaf Key

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Sugarloaf Key

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Enjoy cooking in this well-equipped kitchen with a central island and bar stools, offering a view of the adjacent dining area.

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

9.6 out of 10, Exceptional, (209)
"Outstanding property! Cannot recommend highly enough!"
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
Relax in an outdoor space with a bed, barbecue grill, and lush greenery.

TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!

9.6 out of 10, Exceptional, (90)
"Property was amazing, exactly what is shown in the listing, beds were extremely comfortable, will stay again"
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
Relax by the pool surrounded by lush foliage and enjoy a hot tub on the deck.

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

9.6 out of 10, Exceptional, (81)
"This property is perfectly located near Duval street and within walking distance to the marina. A perfect location for those wanting to shop and enjoy the amenities the marina has to offer. We can’t wait to go back. "
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
Harbor Walk Hideaways | Group Compound In Old Town!
Relax and socialize in this serene patio area, featuring a large table and comfortable seating.

Harbor Walk Hideaways | Group Compound In Old Town!

10.0 out of 10, Exceptional, (5)
"I come to Key West often. This is the best location and property I’ve stayed in. Everything was wonderful. I will book this every single time I come. it is perfect for big families, couples or a group of friends. "
The price is NZ$1,748
includes taxes & fees
11 Aug - 12 Aug
Harbor Walk Hideaways | Group Compound In Old Town!
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
A heated pool

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Stunning hallway with ornate mirror, modern chandelier, and large window.

ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!

9.8 out of 10, Exceptional, (138)
"Really like the home and everything was perfect."
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Relax by the pool in a serene backyard oasis with a wooden deck and shaded gazebo.

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (190)
"We loved the house. From the location, to ambiance and heated pool- it was all amazing! We didn’t cook at all and spent most of our time out and about, but we used the pool day and night. We had 2 couples and 2 additional friends and it was the perfect amount of space and privacy! Would highly recommend this spot and nearby is a cute little bike shop to easily rent a bike cruiser or golf cart for your time! "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Enjoy a spacious living area with a kitchen, dining, and seating space, featuring a sofa, wooden table, and staircase.

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (186)
"The location was excellent—just a short walk to Duval Street. The property was spacious enough to comfortably accommodate our family of five, and having three bathrooms was a big plus."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Pool

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Waterfront luxury home with private pool
Relax in a spacious living area with a dining table, sofa, and comfortable seating.

Waterfront luxury home with private pool

9.8 out of 10, Exceptional, (78)
"We had a wonderful stay at 3/4 time! It is a beautiful VRBO to use in Key West. We truly appreciated all the thoughtful touches that made the place feel like a home away from home.The location was perfect, and the space was clean, comfortable, and well-equipped for a relaxing getaway. We absolueltly loved the heated pool. It was the perfect base for exploring Key West, and we’re already looking forward to our next visit."
Waterfront luxury home with private pool
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
Relax by the pool surrounded by lush tropical vegetation and a covered patio area.

JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL

10.0 out of 10, Exceptional, (108)
"Great place to stay for our spring trip as a family of 3. "
The price is NZ$2,025
includes taxes & fees
5 Aug - 6 Aug
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
Tropical Key West out of the way
Relax in a serene pool area surrounded by lush greenery and palm trees, complete with lounge chairs and umbrellas.

Tropical Key West out of the way

9.4 out of 10, Exceptional, (172)
"Thanks for the stay, we loved the pool and peaceful quiet while still being so close to everything. Family dinners on the porch were also a great and relaxing alternative to every meal out. "
The price is NZ$899
includes taxes & fees
3 Aug - 4 Aug
Tropical Key West out of the way
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Enjoy cooking and dining in this well-equipped kitchen with a central island, oven, and ample counter space.

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!"
The price is NZ$1,018
includes taxes & fees
10 Aug - 11 Aug
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Old Florida Style, wrap around porch, boat basin for dockage, open water
Relax on the waterfront with Adirondack chairs and a small dining table.

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 NZ$1,179
includes taxes & fees
18 Aug - 19 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Dining

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

9.8 out of 10, Exceptional, (136)
"Property was clean and comfortable with everything we needed. Only complaint is the late check in time."
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Enjoy a well-appointed kitchen and living area with stainless steel appliances, a dining table, and a comfortable sofa.

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

10.0 out of 10, Exceptional, (204)
"Wonderful stay!"
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
Relax by the serene pool surrounded by lush greenery and a deck with seating area.

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!

9.8 out of 10, Exceptional, (87)
"Great location "
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Relax by the serene pool surrounded by lush greenery and a comfortable seating area.

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

9.8 out of 10, Exceptional, (218)
"We had a great time and loved the property "
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Relax in a patio area with a hammock, metal table, and chairs, surrounded by a tree and a wooden fence.

KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!

9.8 out of 10, Exceptional, (77)
"We were so happy with our stay! It was clean, easy and in a great spot! Highly recommend this place. "
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Duval Street Suite in Key West
Enjoy cooking and dining in this well-equipped kitchen with modern appliances and a spacious dining area.

Duval Street Suite in Key West

10.0 out of 10, Exceptional, (45)
"Very clean, great location, and would go back"
Duval Street Suite in Key West
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

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Beach , room and grounds are gorgeous Service was excellent!"
Mary 4-night trip
Posted 17 hours ago
Casa Marina Key West, Curio Collection by Hilton