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

Search Guest Houses in Sugarloaf Key

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Sugarloaf Key guest houses

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

1. The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (1,003 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
$180 nightly
The price is $202
Oct 20 - Oct 21
Total with taxes and fees
The Grand Guesthouse
A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

2. The Palms Hotel

The Palms Hotel
3.0 star property
Old Town Key West
9.0 out of 10, Wonderful, (1,003 reviews)
"Loved the small hotel setting! Friendly staff, great location, nice to have breakfast."
United States
Jerry
$198 nightly
The price is $223
Oct 25 - Oct 26
Total with taxes and fees
The Palms Hotel
Lobby

3. The Independent Inn-Adults only

The Independent Inn-Adults only
3.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (64 reviews)
"We fully enjoyed our stay, Owner was very friendly and polite and we highly recommend The Independent Inn!"
United States
Michael
$206 nightly
The price is $227
Oct 25 - Oct 26
Total with taxes and fees
The Independent Inn-Adults only
A tropical outdoor area with palm trees, hanging plants, and string lights.

4. Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (560 reviews)
"Loved our stay! I would definitely stay there again."
United States
Maricela
$199 nightly
The price is $224
Oct 27 - Oct 28
Total with taxes and fees
Douglas House - Adults Only
A covered outdoor seating area with wicker chairs and a glass table, overlooking a lush garden with palm trees and a pool.

5. 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
$258 nightly
The price is $291
Nov 18 - Nov 19
Total with taxes and fees
Curry House
A swimming pool with a blue mosaic wall and a waterfall feature.

6. Colors on White

Colors on White
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (491 reviews)
"The property is very attractive and well maintained. It is a very good value for the reasonable price. Free adjacent parking is a great convenience and money saver. Although there is no staff on the property since there is only 5 units, the staff is at a nearby property and very helpful. Easy walking to restaurants and stores. We had a very favorable stay and will book again."
United States
Harvey
$199 nightly
The price is $224
Oct 26 - Oct 27
Total with taxes and fees
Colors on White
A pool area with lounge chairs, a white fence, and tropical plants.

7. Wicker Guesthouse

Wicker Guesthouse
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (1,003 reviews)
"Location was great"
United States
Kathy
$229 nightly
The price is $258
Oct 25 - Oct 26
Total with taxes and fees
Wicker Guesthouse
A white building with green shutters, surrounded by a white picket fence and palm trees.

8. Kona Kai Oasis

Kona Kai Oasis
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (673 reviews)
"This place is a great location- right down the street from Duval, although it is about a 20 minute walk to the better bars. Very affordable and parking on location, highly recommend!"
United States
Leah
$100 nightly
The price is $113
Oct 20 - Oct 21
Total with taxes and fees
Kona Kai Oasis
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
8.8 out of 10, Excellent, (1,001 reviews)
"Great location and quaint courtyard vibe"
United States
Donna
$216 nightly
The price is $243
Oct 25 - Oct 26
Total with taxes and fees
The Cabana Inn Key West - Adults Only
A green house with a white porch, a flag, and a sign advertising a property for sale.

10. 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, (1,000 reviews)
"Loved the location, breakfast and clean room. Staff, Drew, very friendly and helpful. Will definitely stay here again."
United States
Richard
$179 nightly
The price is $201
Oct 27 - Oct 28
Total with taxes and fees
L'Habitation Guest House - Adults Only
A covered porch with wicker furniture, a ceiling fan, and a view of the street.

11. 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, (48 reviews)
"The place is very cute. The pool was perfect."
United States
Jay
$261 nightly
The price is $290
Oct 26 - Oct 27
Total with taxes and fees
FLAGLER ROOM @ Inn on Fleming~ADULTS ONLY 1st Floor King w/Community Pool
A wooden boardwalk leading to a beach with palm trees and a clear sky.

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, (1,002 reviews)
"If you like an old historical place to stay, this is it. Great location, big rooms, great atmosphere, free parking (bonus)"
United States
chris
$240 nightly
The price is $270
Oct 27 - Oct 28
Total with taxes and fees
Amsterdam's Curry Mansion Inn
A gated entrance with lush green foliage and a white picket fence.

13. Coco Plum Inn

Coco Plum Inn
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (569 reviews)
"Location was perfect"
United States
August
$215 nightly
The price is $242
Oct 20 - Oct 21
Total with taxes and fees
Coco Plum 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, (172 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.
$253 nightly
The price is $281
Oct 25 - Oct 26
Total with taxes and fees
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.

15. Duval Inn

Duval Inn
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (839 reviews)
"The room was nice and quaint, pool was clean and well kept. The staff was friendly and very helpful. Would stay there again."
United States
Arnold J
$235 nightly
The price is $265
Oct 25 - Oct 26
Total with taxes and fees
Duval Inn
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
$279 nightly
The price is $314
Oct 29 - Oct 30
Total with taxes and fees
Duval Gardens - Adults Only
A pool area with a blue table and chairs, surrounded by palm trees and a white building.

17. Banana's Foster Guesthouse

Banana's Foster Guesthouse
2.0 star property
Key West Historic District
8.6 out of 10, Excellent, (24 reviews)
"Perfect location and lovely place!"
United States
michael
$287 nightly
The price is $322
Nov 16 - Nov 17
Total with taxes and fees
Banana's Foster Guesthouse
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, (329 reviews)
"A great place to stay, a couple of blocks from the action."
United Kingdom
Adam
$266 nightly
The price is $299
Oct 20 - Oct 21
Total with taxes and fees
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, (101 reviews)
"Adorable accommodations, great hosts & location. We’ll absolutely stay here again! "
United States
Kara W.
$344 nightly
The price is $382
Oct 26 - Oct 27
Total with taxes and fees
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
9.6 out of 10, Exceptional, (30 reviews)
"House is in a great location, walking distance to shops and Historic Harbor."
United States
Kevin M.
$253 nightly
The price is $281
Oct 26 - Oct 27
Total with taxes and fees
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

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Pros: great location, nice pool area, clean room, price good for the area, friendly staff. Cons: ice machine near our room broken, one of the elevators was out of order, bed uncomfortably firm, despite the website saying they had dinner inside the only food choices were from the poolside bar. Still waiting on the itemized bill, believe we were overcharged on “extras”."
Lisa 2-night trip
Posted less than an hour ago
Hilton Garden Inn Key West / The Keys Collection

Find out more about Sugarloaf Key

Sugarloaf Key Guest Houses information

Number of reviews
6,578
Accommodation
64 Guest Houses
Lowest Price
$113
Highest Price
$382

Frequently asked questions

What is the nightly rate for a guest house in Sugarloaf Key?
Rates for Sugarloaf Key guest houses vary, but travelers can find great-value prices from $113 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Sugarloaf Key guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Sugarloaf Key guest house and a B&B?
A guest house in Sugarloaf Key is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

Explore a world of travel with Expedia