Sugarloaf Key Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Sugarloaf Key Vacation Homes

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, (2)
"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!
Spec @125.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
Relax in a patio area with a wooden deck, featuring a table and two chairs.

Spec @125.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio

9.0 out of 10, Wonderful, (170)
"This was a great location and easy place to stay. We were able to walk to many locations in Old Town. The new updates are a nice addition to this location. Fresh paint, refrigerator, A/C and the patio is a great place to relax. "
Spec @125.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
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, (140)
"Really like the home and everything was perfect."
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
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. "
Tropical Key West out of the way
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 CA $413
CA $960 total
includes taxes & fees
Aug 18 - Aug 19
Old Florida Style, wrap around porch, boat basin for dockage, open water
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!
Luxury two floor apartment in prime location of famous Duval Street
Relax on a crescent-shaped beach with turquoise waters and lush green surroundings.

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (82)
"Perfect place to stay. Great location. "
The price is CA $406
CA $992 total
includes taxes & fees
Aug 12 - Aug 13
Luxury two floor apartment in prime location of famous Duval Street
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Relax on the deck overlooking the marina, where you can enjoy dining or unwind with a kayak nearby.

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.4 out of 10, Exceptional, (48)
"Clean, home included everything you could need. Best of all, communication was clear, friendly, professional and a binder was left with activities, restaurants, etc. Parking spot was clear and easy. Beautiful stay"
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
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
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, (82)
"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!
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Relax in a serene outdoor space with a table and two chairs, surrounded by lush greenery and a view of the pool.

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!

9.8 out of 10, Exceptional, (76)
"Had a great time, easy check in and great location!"
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Enjoy a serene beach experience with a clear ocean view, lounge chairs, and a dock for water activities.

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 CA $402
CA $947 total
includes taxes & fees
Aug 16 - Aug 17
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Relax in style with a hot tub and outdoor seating area, perfect for social gatherings or a peaceful retreat.

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"The units were perfect and the customer service was amazing. "
The price is CA $354
CA $1,154 total
includes taxes & fees
Aug 31 - Sep 1
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
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!
Oceanfront 4-Bed 3-Bath home with pool
Relax on the serene deck overlooking a tranquil body of water surrounded by lush greenery.

Oceanfront 4-Bed 3-Bath home with pool

9.6 out of 10, Exceptional, (74)
"It was a great location in the back, not on the main road. Very quiet, great view, and good place for kids if you are traveling with kids. Used golf carts and was able to get everywhere in 5-10 mins. Overall great vacation and awesome location to stay. "
Oceanfront 4-Bed 3-Bath home with pool
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)
"Great place. well located. Will be returning."
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking
Relax in the serene patio area with a round table and wicker chairs, surrounded by lush greenery and a barbecue grill.

Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking

9.8 out of 10, Exceptional, (18)
"We had a great time in Key West. The location of this property was great, allowing us to walk pretty much everywhere we wanted to go. The unit was clean and provided all the basics we needed. Will definitely consider staying here again."
The price is CA $190
CA $595 total
includes taxes & fees
Aug 31 - Sep 1
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking
Oceanview home with private pool & lush landscaping!
Relax in a serene outdoor oasis with a patio, wicker lounge chairs, and a refreshing pool.

Oceanview home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (113)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Oceanview home with private pool & lush landscaping!
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
Relax by the pool surrounded by lush greenery and a tranquil atmosphere.

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

9.8 out of 10, Exceptional, (224)
"Such a perfect location! Great stay!"
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Stunning marina surrounded by lush greenery and calm waters.

Luxury 3-Bedroom Waterfront Home with Pool AND Dock!

9.8 out of 10, Exceptional, (130)
"Our Key West trip and this property were great. The house had everything we needed and breathtaking views!"
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sugarloaf Key Hotel Reviews

Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

10/10 Excellent
"Staff is personable and efficient, knowledgeable about local activities. The bed was very comfortable. Refrigerator and microwave was a great option for reheating leftovers. The included continental breakfast and free shuttle to town was an awesome convenience feature!"
Terence 5-night trip
Posted 2 days ago
Fairfield Inn and Suites by Marriott Key West