Search Vacation Homes in Sugarloaf Key

    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
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 814 Vacation Homes in Sugarloaf Key with updated reviews, rates, and availability.

Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (44)
"Lovely home to stay in for a couple of nights on Key West"
The price is SAR 729
SAR 1,268 total
includes taxes & fees
5 Jun - 6 Jun
Poolside Cottage #411
Wahoo Way | Charming Hideaway On Duval Street!
1 bedroom, free WiFi, bed sheets

Wahoo Way | Charming Hideaway On Duval Street!

9.4 out of 10, Exceptional, (12)
"Small place, but clean and everything needed for 2 people to stay I "
The price is SAR 459
SAR 1,165 total
includes taxes & fees
3 Jun - 4 Jun
Wahoo Way | Charming Hideaway On Duval Street!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Interior

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

9.8 out of 10, Exceptional, (134)
"Very close to everything, fully recommended"
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
1 bedroom, WiFi, bed sheets

Yellowfin Ledge | Inviting Getaway On Duval! Balcony!

9.4 out of 10, Exceptional, (16)
"This property was in a perfect location in Key West. Just outside the downtown craziness. Everything right in walking distance. "
The price is SAR 557
SAR 1,350 total
includes taxes & fees
2 Jun - 3 Jun
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (146)
"Good location "
The price is SAR 1,313
SAR 2,584 total
includes taxes & fees
29 Jun - 30 Jun
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (48)
"It was just the right place for my family. We really enjoyed the view and close proximity to Key West. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
Terrace/patio

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

9.8 out of 10, Exceptional, (86)
"Great location, great property. My spouse and 2 adult kids plus significant others stayed. Would definitely stay again!"
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Terrace/patio

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

9.0 out of 10, Wonderful, (4)
"The units were perfect and the customer service was amazing. "
The price is SAR 1,317
SAR 3,589 total
includes taxes & fees
1 Jun - 2 Jun
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
June Spec 129.+ 6-8 til 6-20 NEWLY Redone. Not shown in current pics
Terrace/patio

June Spec 129.+ 6-8 til 6-20 NEWLY Redone. Not shown in current pics

9.0 out of 10, Wonderful, (164)
"This unit was perfect! Nice updates and a comfortable space close to everything"
June Spec 129.+ 6-8 til 6-20 NEWLY Redone. Not shown in current pics
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds

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

9.2 out of 10, Wonderful, (44)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We stayed at this location with friends. It was the perfect size for 2 couples and the first thing we noticed was how clean it was. We also enjoyed sitting out on the deck by the water."
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Fandango - private pool
Pool

Fandango - private pool

9.8 out of 10, Exceptional, (78)
"My family and I had a great time staying at Fandago. It was located close enough to Key West to visit, yet far enough away to enjoy some privacy and peace and quiet. We were there for my daughter's wedding and everything was absolutely perfect! Would definitely stay again!"
Fandango - private pool
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
Exterior detail

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (193)
"Great place. Quiet and relaxing yet close to everything Key West!"
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Terrace/patio

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

9.8 out of 10, Exceptional, (69)
"Had a great time, easy check in and great location!"
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen
Exterior detail

Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen

9.6 out of 10, Exceptional, (218)
"The host was very friendly and easy to communicate with. Excellent property in a great neighborhood! Will definitely consider staying here again."
Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen
The Bahama House - Key West
Pool

The Bahama House - Key West

The Bahama House - Key West
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
A heated pool

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

9.8 out of 10, Exceptional, (129)
"All rooms have own bathroom which was very nice. They were also nice size rooms. Had a great stay!"
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
A heated pool

Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only

10.0 out of 10, Exceptional, (176)
"Accomadations were great for our party of four. Plenty of room with all the luxuries of home. The location is outstanding for Duvall Street.entertaiment.Would book again. "
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
Luxury two floor apartment in prime location of famous Duval Street
Beach towels

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (80)
"We loved the location and style of this apartment. Perfect for small families or couples. "
The price is SAR 1,107
SAR 2,690 total
includes taxes & fees
16 Jun - 17 Jun
Luxury two floor apartment in prime location of famous Duval Street
Harbor Walk Hideaways | Group Compound In Old Town!
Outdoor dining

Harbor Walk Hideaways | Group Compound In Old Town!

10.0 out of 10, Exceptional, (3)
"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 SAR 1,650
SAR 4,074 total
includes taxes & fees
22 Jun - 23 Jun
Harbor Walk Hideaways | Group Compound In Old Town!
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Marina

Luxury 3-Bedroom Waterfront Home with Pool AND Dock!

9.8 out of 10, Exceptional, (126)
"Better than advertised. Would stay again."
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