A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

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Check prices for these dates

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Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
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Oct 23 - Oct 25
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Nov 20 - Nov 22

Our top choices for Key West 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, (1,001 reviews)
"The room was great, with a really nice sized bathroom for DT Key West! Everything was very clean and well kept and the AC was nice and cool! The bed was very comfortable as well."
United States
Alissa
The price is P7,078
P9,532 total
includes taxes & fees
Sep 27 - Sep 28
The Grand Guesthouse
A tropical outdoor area with palm trees, hanging plants, and string lights.

2. Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (536 reviews)
"Great place to stay! Awesome Property and Management!"
United States
michael
The price is P7,876
P9,747 total
includes taxes & fees
Oct 5 - Oct 6
Douglas House - Adults Only
A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.

3. Duval Inn

Duval Inn
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (834 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
The price is P8,721
P12,988 total
includes taxes & fees
Oct 1 - Oct 2
Duval Inn
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, (662 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
The price is P6,541
P7,359 total
includes taxes & fees
Sep 27 - Sep 28
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, (1,000 reviews)
"Great little spot, me and my wife always stay here when we visit Key West"
United States
Zachary
The price is P8,484
P10,957 total
includes taxes & fees
Sep 27 - Sep 28
The Palms Hotel
A breakfast setup with wine bottles, fruits, and pastries on a tray by a door with a view of a staircase and greenery.

6. 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 P8,399
P12,266 total
includes taxes & fees
Sep 27 - Sep 28
The Cabana Inn Key West - Adults Only
A gated entrance with lush green foliage and a white picket fence.

7. Coco Plum Inn

Coco Plum Inn
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (559 reviews)
"Perfect stay, we will be back!"
United States
Jake
The price is P8,408
P9,459 total
includes taxes & fees
Sep 28 - Sep 29
Coco Plum Inn
A wooden boardwalk leading to a beach with palm trees and a clear sky.

8. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
3.0 star property
Key West Historic District
8.2 out of 10, Very good, (1,004 reviews)
"Great location. Great hotel."
United States
Tiffany N
The price is P8,800
P9,900 total
includes taxes & fees
Sep 28 - Sep 29
Amsterdam's Curry Mansion Inn
A pool area with lounge chairs, a white fence, and tropical plants.

9. Wicker Guesthouse

Wicker Guesthouse
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (1,002 reviews)
"Awesome place to stay!"
United States
michael
The price is P9,348
P10,516 total
includes taxes & fees
Sep 29 - Sep 30
Wicker Guesthouse
A living room with a ceiling fan, a sofa, a TV, and a bookshelf.

10. The Independent Inn - Formerly Heron House Court

The Independent Inn - Formerly Heron House Court
3.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1,002 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 P6,460
P9,344 total
includes taxes & fees
Sep 28 - Sep 29
The Independent Inn - Formerly Heron House Court
A covered porch with white railings, a ceiling fan, and a table with chairs.

11. The Porch on Frances Inn

The Porch on Frances Inn
4.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (144 reviews)
"Nice cozy hotel close to everything"
United States
Marcos
The price is P7,328
P10,123 total
includes taxes & fees
Sep 29 - Sep 30
The Porch on Frances Inn
A room with a bed, a ceiling fan, and a window with blinds.

12. The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (323 reviews)
"The property was at a great location, safe, very clean, and helpful staff. The breakfast was wonderful, charming outdoor seating."
United States
Brian
The price is P11,274
P12,683 total
includes taxes & fees
Sep 28 - Sep 29
The Mermaid & Alligator
A covered outdoor seating area with wicker chairs and a glass table, overlooking a lush garden with palm trees and a pool.

13. Curry House

Curry House
2.0 star property
Old Town Key West
7.0 out of 10, Good, (70 reviews)
The price is P5,806
P16,748 total
includes taxes & fees
Sep 27 - Sep 28
Curry House
A swimming pool with a blue mosaic wall and a waterfall feature.

14. Colors on White

Colors on White
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (488 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
The price is P7,938
P8,931 total
includes taxes & fees
Sep 27 - Sep 28
Colors on White
A pool area with a blue table and chairs, surrounded by palm trees and a white building.

15. Banana's Foster Guesthouse

Banana's Foster Guesthouse
2.0 star property
Key West Historic District
8.4 out of 10, Very good, (22 reviews)
"Pet friendly. And very close to the marina and Duval St."
United States
TED
The price is P7,948
P19,158 total
includes taxes & fees
Sep 27 - Sep 28
Banana's Foster Guesthouse
A pool area with a wooden deck, lounge chairs, and umbrellas.

16. The Key West Hotel

The Key West Hotel
3.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (562 reviews)
"Great place to stay - highly recommend."
United States
Preston
The price is P17,407
P24,163 total
includes taxes & fees
Sep 27 - Sep 28
The Key West Hotel
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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Top Key West Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"From before we arrived we already knew we chose the right place to stay! We had questions about parking our motorcycle on property and there was no hesitation to share information and also connect with us. The staff is great. We are recommending this location and properties to friends and family. Next time we’re in town, 100% this will be the place we stay. Location is great and the property is fun to explore. Thank you all for making our stay memorable!"
Rebecca 2-night trip
Posted 12 hours ago
Winslow's Bungalows - Key West Historic Inns

Find out more about Key West

Key West Guest Houses information

Number of reviews
8,211
Accommodation
27 Guest Houses
Lowest Price
P7,359
Highest Price
P24,163

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