A waterfront with a pier, calm water, and houses with palm trees in the background.

Search Guest Houses in Sugarloaf Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 Dec

Our top choices for Sugarloaf Key guest houses

A tropical outdoor area with palm trees, hanging plants, and string lights.

1. Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (572 reviews)
"Loved our stay! I would definitely stay there again."
United States
Maricela
The price is SAR 531
SAR 658 total
includes taxes & fees
29 Oct - 30 Oct
Douglas House - Adults Only
Room

2. The Independent Inn

The Independent Inn
3.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (66 reviews)
"We fully enjoyed our stay, Owner was very friendly and polite and we highly recommend The Independent Inn!"
United States
Michael
The price is SAR 435
SAR 629 total
includes taxes & fees
29 Oct - 30 Oct
The Independent Inn
A breakfast buffet with various food items and a chalkboard menu listing options like 'Martins', 'Hot Tin Roof', and 'B.O.S. Fishwagon'.

3. The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (1,000 reviews)
"Fun apartment style living in Key West…fun little patio with coffee and continental breakfast. Make sure you look at the check in hours :) great spot makes you feel local"
United States
Justyn
The price is SAR 583
SAR 750 total
includes taxes & fees
29 Oct - 30 Oct
The Grand Guesthouse
A white building with green shutters, surrounded by a white picket fence and palm trees.

4. Kona Kai Oasis

Kona Kai Oasis
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (682 reviews)
"Not bad for the price . Great location!"
United States
Parker
The price is SAR 682
SAR 767 total
includes taxes & fees
2 Nov - 3 Nov
Kona Kai Oasis
A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

5. The Palms Hotel

The Palms Hotel
3.0 star property
Old Town Key West
9.0 out of 10, Wonderful, (1,005 reviews)
"great staff, clean place ,"
United States
mark
The price is SAR 657
SAR 824 total
includes taxes & fees
29 Oct - 30 Oct
The Palms Hotel
A green house with a white porch, a flag, and a sign advertising a property for sale.

6. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
2.5 star property
Key West Historic District
9.4 out of 10, Exceptional, (1,002 reviews)
"Loved the location, breakfast and clean room. Staff, Drew, very friendly and helpful. Will definitely stay here again."
United States
Richard
The price is SAR 585
SAR 658 total
includes taxes & fees
1 Nov - 2 Nov
L'Habitation Guest House - Adults Only
A white building with a grey roof, surrounded by potted plants and a blue umbrella.

7. The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only
3.0 star property
Old Town Key West
9.0 out of 10, Wonderful, (1,006 reviews)
"Great location and quaint courtyard vibe"
United States
Donna
The price is SAR 571
SAR 811 total
includes taxes & fees
1 Nov - 2 Nov
The Cabana Inn Key West - Adults Only
A covered outdoor seating area with wicker chairs and a glass table, overlooking a lush garden with palm trees and a pool.

8. Curry House

Curry House
2.0 star property
Old Town Key West
7.0 out of 10, Good, (71 reviews)
"An excellent location in town for a visit. We were up on third floor great view especially from porch…tough getting up stairs w luggage. Overall a wonderful visit. Beautiful location and just antique enough! Cheers"
United States
donald
The price is SAR 399
SAR 1,061 total
includes taxes & fees
18 Nov - 19 Nov
Curry House
A wooden deck with a hot tub, surrounded by tropical vegetation and a bungalow-style house with a sloped roof.

9. Wicker Guesthouse

Wicker Guesthouse
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (1,001 reviews)
"Great place to stay. Always love coming back here."
United States
Cheyenne
The price is SAR 672
SAR 756 total
includes taxes & fees
29 Oct - 30 Oct
Wicker Guesthouse
A pool area with a blue table and chairs, surrounded by palm trees and a white building.

10. Banana's Foster Guesthouse

Banana's Foster Guesthouse
2.0 star property
Key West Historic District
8.6 out of 10, Excellent, (26 reviews)
"Perfect location and lovely place!"
United States
michael
The price is SAR 516
SAR 1,192 total
includes taxes & fees
16 Nov - 17 Nov
Banana's Foster Guesthouse
A gated entrance with lush green foliage and a white picket fence.

11. Coco Plum Inn

Coco Plum Inn
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (574 reviews)
"Location was perfect"
United States
August
The price is SAR 909
SAR 1,023 total
includes taxes & fees
4 Nov - 5 Nov
Coco Plum Inn
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.

12. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
3.0 star property
Key West Historic District
8.0 out of 10, Very good, (1,000 reviews)
"Great location!"
United States
carmen
The price is SAR 838
SAR 1,323 total
includes taxes & fees
22 Nov - 23 Nov
Amsterdam's Curry Mansion Inn
A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.

13. Duval Inn

Duval Inn
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (843 reviews)
"Kind staff. Very helpful and cute property. Room was kinda small but I knew what I was getting into. 100% would stay again"
United States
Ramses
The price is SAR 480
SAR 730 total
includes taxes & fees
29 Oct - 30 Oct
Duval Inn
A covered porch with wicker furniture, a ceiling fan, and a view of the street.

14. FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool

FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool
Old Town Key West
10.0 out of 10, Exceptional, (50 reviews)
"The place is very cute. The pool was perfect."
United States
Jay
The price is SAR 511
SAR 1,162 total
includes taxes & fees
2 Nov - 3 Nov
FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool
A bedroom with a bed, a ceiling fan, a wall-mounted TV, and a door.

15. Colors on White

Colors on White
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (494 reviews)
"Check-in was easy. Property was very dirty, does not look like they clean the floors at all.. water pressure awful. Property definitely needs some updating.."
United States
Kellie
The price is SAR 689
SAR 775 total
includes taxes & fees
29 Oct - 30 Oct
Colors on White
A two-story building with a white picket fence, palm trees, and a sign that reads 'DUVAL GARDENS.'

16. Duval Gardens - Adults Only

Duval Gardens - Adults Only
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (925 reviews)
"Great rooms and staff, the breakfast is amazing "
United States
JoAnn
The price is SAR 727
SAR 1,071 total
includes taxes & fees
10 Nov - 11 Nov
Duval Gardens - Adults Only
A covered outdoor area with a table and chairs, surrounded by white railings and palm trees.

17. CORONA ~ Adults Only, 2nd Floor King Room w/ Community Pool at Azul Mansion!

CORONA ~ Adults Only, 2nd Floor King Room w/ Community Pool at Azul Mansion!
Old Town Key West
9.6 out of 10, Exceptional, (197 reviews)
"It was a nice weekend getaway. Great location."
United States
The Rogue P.
The price is SAR 465
SAR 1,112 total
includes taxes & fees
29 Oct - 30 Oct
CORONA ~ Adults Only, 2nd Floor King Room w/ Community Pool at Azul Mansion!
A room with a bed, a ceiling fan, and a window with blinds.

18. The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (331 reviews)
"such a lovely location. nice and quiet for a restful stay. staff was attentive to all our needs. would definitely return"
United States
christine
The price is SAR 1,220
SAR 1,372 total
includes taxes & fees
22 Nov - 23 Nov
The Mermaid & Alligator
A pool with a waterfall feature, surrounded by lush greenery and a white building with green shutters.

19. KEITT ~ Adult Only, 2nd Floor 1 Bedroom w/ Community Pool!

KEITT ~ Adult Only, 2nd Floor 1 Bedroom w/ Community Pool!
Old Town Key West
9.8 out of 10, Exceptional, (103 reviews)
"Adorable accommodations, great hosts & location. We’ll absolutely stay here again! "
United States
Kara W.
The price is SAR 807
SAR 1,686 total
includes taxes & fees
24 Nov - 25 Nov
KEITT ~ Adult Only, 2nd Floor 1 Bedroom w/ Community Pool!
A covered porch with wicker furniture, a ceiling fan, and a view of the street.

20. GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Community Pool!

GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Community Pool!
Old Town Key West
9.8 out of 10, Exceptional, (31 reviews)
"House is in a great location, walking distance to shops and Historic Harbor."
United States
Kevin M.
The price is SAR 473
SAR 1,120 total
includes taxes & fees
3 Nov - 4 Nov
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Community Pool!
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.
View all properties
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

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Staf was super friendly and responsive. Location was great. Close enough to Duval Street, but far enough to enjoy peace and quiet. Would definitely stay again"
Danielle 4-night trip
Posted 1 hour ago
Winslow's Bungalows - Key West Historic Inns