Search Guest Houses in Sugarloaf Key from CA $149

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Sugarloaf Key guest houses

A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

1. The Palms Hotel

The Palms Hotel
3.0 star property
Old Town Key West
9.0 out of 10, Wonderful, (1,004 reviews)
"Clean rooms, Good area, Excellent breakfast, friendly staff at a Good price"
Canada
William
The price is CA $275
CA $341 total
includes taxes & fees
Nov 17 - Nov 18
The Palms Hotel
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

2. The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (1,001 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 CA $272
CA $341 total
includes taxes & fees
Dec 6 - Dec 7
The Grand Guesthouse
A tropical outdoor area with palm trees, hanging plants, and string lights.

3. Douglas House - Adults Only

Douglas House - Adults Only
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (583 reviews)
"Loved our stay! I would definitely stay there again."
United States
Maricela
The price is CA $272
CA $393 total
includes taxes & fees
Nov 17 - Nov 18
Douglas House - Adults Only
A green house with a white porch, a flag, and a sign advertising a property for sale.

4. 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)
"A very cute, cozy and comfortable place to stay especially for old Key West charm. Will definitely stay here again."
United States
Callie
The price is CA $238
CA $267 total
includes taxes & fees
Dec 1 - Dec 2
L'Habitation Guest House - Adults Only
Room

5. The Independent Inn

The Independent Inn
3.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (70 reviews)
"Dan and Emma own the property and they go out of their way to give you the best experience you can receive. They are continuously on the property, working trying to maintain and make improvements. Thoroughly enjoyed the stay."
United States
Malcolm
The price is CA $250
CA $337 total
includes taxes & fees
Dec 7 - Dec 8
The Independent Inn
A covered outdoor seating area with wicker chairs and a glass table, overlooking a lush garden with palm trees and a pool.

6. Curry House

Curry House
2.0 star property
Old Town Key West
7.0 out of 10, Good, (72 reviews)
"Very nice, clean and quiet. I think we were the only ones on the property. Bathroom looked recently remodeled, very nice."
United States
MICHAEL
The price is CA $150
CA $397 total
includes taxes & fees
Nov 18 - Nov 19
Curry House
A covered porch with wicker furniture, a ceiling fan, and a view of the street.

7. 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 CA $158
CA $395 total
includes taxes & fees
Dec 1 - Dec 2
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Community Pool!
A two-story building with a white picket fence, palm trees, and a sign that reads 'DUVAL GARDENS.'

8. 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 CA $220
CA $303 total
includes taxes & fees
Nov 22 - Nov 23
Duval Gardens - Adults Only
A breakfast setup with wine bottles, fruits, and pastries on a tray by a door with a view of a staircase and greenery.

9. 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, (1,007 reviews)
"Staff was great, hotel was quaint and clean."
United States
Casey
The price is CA $251
CA $345 total
includes taxes & fees
Nov 8 - Nov 9
The Cabana Inn Key West - Adults Only
A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.

10. Duval Inn

Duval Inn
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (849 reviews)
"Bed was very comfortable, and the location was a quick walk to anything."
United States
April
The price is CA $278
CA $384 total
includes taxes & fees
Nov 30 - Dec 1
Duval Inn
A white building with green shutters, surrounded by a white picket fence and palm trees.

11. Kona Kai Oasis

Kona Kai Oasis
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (685 reviews)
"Not bad for the price . Great location!"
United States
Parker
The price is CA $254
CA $285 total
includes taxes & fees
Nov 15 - Nov 16
Kona Kai Oasis
A pool area with lounge chairs, a white fence, and tropical plants.

12. Wicker Guesthouse

Wicker Guesthouse
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay. Always love coming back here."
United States
Cheyenne
The price is CA $326
CA $366 total
includes taxes & fees
Nov 29 - Nov 30
Wicker Guesthouse
A wooden boardwalk leading to a beach with palm trees and a clear sky.

13. 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 CA $308
CA $488 total
includes taxes & fees
Nov 22 - Nov 23
Amsterdam's Curry Mansion Inn
A living room with two sofas, a coffee table, and a window with blinds.

14. HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!

HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
Old Town Key West
9.6 out of 10, Exceptional, (173 reviews)
"One of our best vacations ever. Our room was steps from the pool and common areas. I would highly recommend staying here."
United States
Vicki L.
The price is CA $165
CA $404 total
includes taxes & fees
Nov 30 - Dec 1
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
A swimming pool with a waterfall feature, surrounded by tropical foliage.

15. Colors on White

Colors on White
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (495 reviews)
"xfr"
United States
edward
The price is CA $301
CA $338 total
includes taxes & fees
Nov 23 - Nov 24
Colors on White
A pool area with a blue table and chairs, surrounded by palm trees and a white building.

16. 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 CA $202
CA $456 total
includes taxes & fees
Nov 24 - Nov 25
Banana's Foster Guesthouse
A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

17. Coco Plum Inn

Coco Plum Inn
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (577 reviews)
"Location was perfect"
United States
August
The price is CA $372
CA $418 total
includes taxes & fees
Nov 16 - Nov 17
Coco Plum Inn
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 CA $443
CA $499 total
includes taxes & fees
Nov 29 - Nov 30
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 CA $252
CA $568 total
includes taxes & fees
Nov 10 - Nov 11
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. 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, (51 reviews)
"Absolutely a wonderful, peaceful location. Was able to take a dip in the pool entirely by myself. Had a nice little community area with a kitchen. The watercrafts for the room and the filtered water were an incredibly great touch. Would definitely stay here again."
United States
Michael
The price is CA $181
CA $423 total
includes taxes & fees
Nov 30 - Dec 1
FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King 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.
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Learn more about Sugarloaf Key

Kayak through mangrove tunnels and spot colourful fish in the crystal-clear waters surrounding this laid-back island. Unwind on Sugarloaf Beach's white sands or explore Upper Sugarloaf Sound, where local boaters know the best snorkelling spots.

See all hotels in Sugarloaf Key
A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

Top reviews in Sugarloaf Key

A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only

Douglas House - Adults Only

Douglas House - Adults Only
Old Town Key West

10/10 Excellent

Absolutely recommend this property. Close to everything, super clean and amenities showed a lot of thought. The pool was lovely. Maria who checked us in took all the time to show us around, give us the low down on the area etc.
Canada
Heather
Reviewed February 9, 2025
Douglas House - Adults Only

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