Search Sugarloaf Key Villa Rentals from CA $344

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

Browse Select Sugarloaf Key Villas

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Enjoy meals in this stylish dining area with a large table for four, comfortable seating, and a pendant light above.

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere

9.8 out of 10, Exceptional, (157)
"We have stayed here now at least a few years in a row, and it continues to be wonderful. You cannot beat the location for convenience and to enjoy the music from next door at Willy T's. We love sitting on the balcony overlooking Duval Street and taking in all of those sights and sounds from the comfort of home! Sun is plenty on the rooftop patio, while the pool stays mostly shaded. Parking is easy, and the owner and property manager are both delightful. The music next door can be loud at night,...
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Enjoy a relaxing stay in this two-story home with a balcony, pool, and hot tub area.

Two Bedroom Two Bath Poolside Villa Steps from Duval!

10.0 out of 10, Exceptional, (42)
"Loved staying here, easy walking to everything we wanted to do. We had a 2 bedroom and were very comfortable, beds were really comfy. Pool area was a nice place to hang out after dinner. Would stay again for sure "
The price is CA $690
CA $875 total
includes taxes & fees
Aug 12 - Aug 13
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Dine in style with a large table set for four, surrounded by a contemporary design and a beautiful outdoor view.

Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking

9.8 out of 10, Exceptional, (77)
"We loved our stay at this Keywest property. It’s a perfect spot for a celebration getaway. There is Willy T’s next door with live music so you have entertainment on your patio with amazing music. The property is large enough with the two pools and 6 rooms to host a large group. You can walk everywhere as it’s in the center of all the shops and restaurants. Would definitely love to stay again. Thank you! "
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access
Enjoy a serene beachside picnic amidst tall pine trees and the soothing ocean views.

Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access

10.0 out of 10, Exceptional, (32)
"The property was beautiful and spacious. My whole family was comfortable and enjoyed."
Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Relax by the pool on the spacious balcony with a shaded seating area.

Two Bedroom Two Bath Balcony Villa Steps from Duval!

10.0 out of 10, Exceptional, (40)
"Great place to stay and great owners!"
The price is CA $690
CA $875 total
includes taxes & fees
Aug 4 - Aug 5
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Poolside Studio Villa Steps from Duval!
Enjoy a relaxing stay in this two-story residence with a balcony, pool, and hot tub area.

Poolside Studio Villa Steps from Duval!

10.0 out of 10, Exceptional, (20)
"Great place to stay"
The price is CA $344
CA $434 total
includes taxes & fees
Aug 3 - Aug 4
Poolside Studio Villa Steps from Duval!
Atlantic View Luxury Villa with Pool
Relax by the serene pool surrounded by lush greenery and a white picket fence.

Atlantic View Luxury Villa with Pool

3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
The price is CA $823
CA $1,410 total
includes taxes & fees
Aug 2 - Aug 3
Atlantic View Luxury Villa with Pool
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Relax in this serene bedroom with a large bed, ceiling fan, and a balcony offering a view of lush greenery.

Secret Villa II @ Old Town: with Private Pool, close to Duval!

10.0 out of 10, Exceptional, (145)
"Loved how it was secluded but yet accessible to everything. "
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
House (2 Bedrooms) | Interior

Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool

4.0 star property
6.0 out of 10, (2)
"The accommodations were very nice and comfortable. The place was clean and well maintained. TV/cable instructions would have been very helpful. The upstairs hallway smoke detector triggered for no apparent reason and i had to stand on a stool to deactivate it -kind of dangerous."
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
Secret Villa I @ Old Town with Private Pool, close to Duval!
Relax in a serene outdoor space with a glass-enclosed patio, metal table, and comfortable lounge chairs overlooking a swimming pool surrounded by lush greenery.

Secret Villa I @ Old Town with Private Pool, close to Duval!

10.0 out of 10, Exceptional, (161)
"Perfect place. Great hosts. We had a wonderful time!"
Secret Villa I @ Old Town with Private Pool, close to Duval!
Loft Villa Steps from Duval!
Enjoy a refreshing swim and al fresco dining by the pool, surrounded by lush greenery and a scenic view.

Loft Villa Steps from Duval!

10.0 out of 10, Exceptional, (16)
"Can’t say enough great things about this place. From the hosts to the property itself, top notch!"
The price is CA $455
CA $577 total
includes taxes & fees
Aug 4 - Aug 5
Loft Villa Steps from Duval!
Emerald Seas - Florida Keys Ocean Front Paradise!
Enjoy serene views of the lake from this balcony with a table for dining or relaxation.

Emerald Seas - Florida Keys Ocean Front Paradise!

10.0 out of 10, Exceptional, (18)
"What a great place to stay!!! We enjoyed watching the fish every night right off the dock. Shawn and Cindy were very accommodating when we wanted to extend our stay."
Emerald Seas - Florida Keys Ocean Front Paradise!
Poolside Queen Room Steps from Duval!
Enjoy a relaxing stay in this two-story home with a balcony and access to a swimming pool and hot tub.

Poolside Queen Room Steps from Duval!

10.0 out of 10, Exceptional, (1)
"Perfect location, awesome hosts, and the Key West Villas were wonderful. The pool area provided a tranquil area to relax."
The price is CA $344
CA $436 total
includes taxes & fees
Aug 9 - Aug 10
Poolside Queen Room Steps from Duval!
Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!
Relax by the pool surrounded by lush greenery and a thatched-roof pavilion.

Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!

9.2 out of 10, Wonderful, (31)
"We enjoyed the stay. The place was clean, the check in and out was easy. Great stay!"
Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!
Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool
Enjoy meals al fresco in this serene outdoor space surrounded by lush greenery and a distant view.

Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool

9.6 out of 10, Exceptional, (13)
"Very comfortable and great location near Marina where we fished."
Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool
One Bedroom Deck Villa Steps from Duval!
Enjoy a shaded outdoor space with a pool and comfortable seating on the balcony.

One Bedroom Deck Villa Steps from Duval!

10.0 out of 10, Exceptional, (6)
"Beautiful property, clean and comfortable suite, friendly staff, fantastic hospitality, ideal central location! We'll be back!"
The price is CA $414
CA $525 total
includes taxes & fees
Aug 4 - Aug 5
One Bedroom Deck Villa Steps from Duval!
Poolside King Room Steps from Duval!
Relax on the balcony with a refreshing dip in the pool, surrounded by lush greenery and comfortable outdoor seating areas.

Poolside King Room Steps from Duval!

10.0 out of 10, Exceptional, (1)
"If you’re looking to stay in Old Town this is the perfect location. Pool right outside the room, FREE Happy Hour from 4-5 and very accommodating hosts. Good for families or couples alike. Awesome!"
The price is CA $386
CA $489 total
includes taxes & fees
Aug 5 - Aug 6
Poolside King Room Steps from Duval!
SOLD - NO LONGER AVAILABLE Serene Canal home in the Heart of the Keys
Step out onto the balcony and take in the serene views of the surrounding landscape.

SOLD - NO LONGER AVAILABLE Serene Canal home in the Heart of the Keys

SOLD - NO LONGER AVAILABLE Serene Canal home in the Heart of the Keys
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
"Good hotel and people friendly. The area is super nice "
Juan 2-night trip
Posted 14 hours ago
Fairfield Inn and Suites by Marriott Key West