Search Guest Houses in Sugarloaf Key

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Sugarloaf Key guest houses

Outdoor spa tub
NYAH Key West - Adults Only

NYAH Key West - Adults Only

NYAH Key West - Adults Only
3.0 star property
Key West Historic District
7.8 out of 10, Good, (1005)
"Great little hotel in the heart of Old Town."
United States
Robert
NYAH Key West - Adults Only
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers
Heron House Court - Adult Only

Heron House Court - Adult Only

Heron House Court - Adult Only
3.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1004)
"Great staff, very friendly. Oerfect location, short walk to Duval, but far enough to get sleep. "
United States
Chandler
The price is AED 1,021
AED 1,288 total
includes taxes & fees
4 Jan - 5 January 2026
Heron House Court - Adult Only
Property grounds
The Palms Hotel

The Palms Hotel

The Palms Hotel
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (1008)
"Good location, nice grounds and friendly staff."
United States
Scott
The price is AED 687
AED 856 total
includes taxes & fees
14 Dec - 15 Dec
The Palms Hotel
Garden
Douglas House

Douglas House

Douglas House
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (220)
"Great location! Clean rooms. Friendly staff"
United States
Brad
The price is AED 503
AED 622 total
includes taxes & fees
15 Dec - 16 Dec
Douglas House
Courtyard
The Cabana Inn Key West - Adults Only

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, (1003)
"Rooms are clean, staff was friendly and pool was refreshing. "
United States
Wendy
The Cabana Inn Key West - Adults Only
Front of property
L'Habitation Guest House

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Key West Historic District
9.4 out of 10, Exceptional, (920)
"Great place close to all. Manager was very helpful in recommending how to get around the island, what to do and where to eat."
United States
Robert
The price is AED 500
AED 563 total
includes taxes & fees
14 Dec - 15 Dec
L'Habitation Guest House
Beach nearby
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
Old Town Key West
9.6 out of 10, Exceptional, (143)
"Great property. Lots of thoughtful amenities. Management friendly and responsive. "
United States
Diane V.
The price is AED 360
AED 965 total
includes taxes & fees
15 Dec - 16 Dec
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
Exterior
The Grand Guesthouse

The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (1001)
"Great stay"
United States
Ginger
The Grand Guesthouse
Poolside bar
Duval Inn

Duval Inn

Duval Inn
3.0 star property
Old Town Key West
8.6 out of 10, Excellent, (715)
"Property was clean and perfect location."
United States
Tracy
Duval Inn
Front of property
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
3.0 star property
Key West Historic District
8.4 out of 10, Very Good, (1000)
"The pool loungers were awesome and it was great having towels for the pool and rooom self service. You are right downtown in the middle of everything so yes there's going to be noise but we had no problem sleeping and felt very safe in the area! We will definitely be back!"
United States
Karla
The price is AED 681
AED 1,138 total
includes taxes & fees
16 Dec - 17 Dec
Amsterdam's Curry Mansion Inn
Fountain
Colors on White

Colors on White

Colors on White
3.0 star property
Old Town Key West
8.0 out of 10, Very Good, (379)
"Very nice place to be at. Close walking and biking distance "
United States
brad
Colors on White
Beach nearby
HEMINGWAY SUITE @ Inn on Fleming~ADULTS ONLY 2nd Lvl King Shared Heated Pool

HEMINGWAY SUITE @ Inn on Fleming~ADULTS ONLY 2nd Lvl King Shared Heated Pool

HEMINGWAY SUITE @ Inn on Fleming~ADULTS ONLY 2nd Lvl King Shared Heated Pool
Old Town Key West
10.0 out of 10, Exceptional, (15)
"Great access to all that key west had to offer"
United States
Dennis M.
The price is AED 382
AED 990 total
includes taxes & fees
19 Dec - 20 Dec
HEMINGWAY SUITE @ Inn on Fleming~ADULTS ONLY 2nd Lvl King Shared Heated Pool
Beach nearby
HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w/ Shared Pool!

HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w/ Shared Pool!

HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w/ Shared Pool!
Old Town Key West
9.8 out of 10, Exceptional, (87)
"Amazing place"
United States
Cecilia
The price is AED 433
AED 1,198 total
includes taxes & fees
15 Dec - 16 Dec
HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w/ Shared Pool!
Superior Villa, 2 Bedrooms, Private Pool (Room 409) | Outdoor pool
New Orleans House - Gay Men Adult Resort

New Orleans House - Gay Men Adult Resort

New Orleans House - Gay Men Adult Resort
2.5 star property
Old Town Key West
8.6 out of 10, Excellent, (340)
"Overall good place to stay. "
United States
David
The price is AED 808
AED 949 total
includes taxes & fees
4 Jan - 5 January 2026
New Orleans House - Gay Men Adult Resort
Exterior
Coco Plum Inn

Coco Plum Inn

Coco Plum Inn
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (462)
"Overall great for couple's stay. "
United States
Quazi
The price is AED 658
AED 740 total
includes taxes & fees
17 Dec - 18 Dec
Coco Plum Inn
Sweet Caroline - Two Bedroom Spacious Apartment | Private kitchen | Microwave
Banana's Foster Guesthouse

Banana's Foster Guesthouse

Banana's Foster Guesthouse
2.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (7)
"The hotel is an old building built in the 1800s and it shows the condition of the rooms were not perfect. It was OK for the few days we needed to stay but for the price the chain hotel might be better."
United States
Charles
Banana's Foster Guesthouse
Outdoor pool
The Key West Hotel

The Key West Hotel

The Key West Hotel
2.5 star property
Key West Historic District
9.2 out of 10, Wonderful, (511)
"location was great nice bar party vibe"
United States
Robert Howard
The price is AED 813
AED 1,117 total
includes taxes & fees
11 Dec - 12 Dec
The Key West Hotel
Beach nearby
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Old Town Key West
9.8 out of 10, Exceptional, (103)
"Super clean beautiful place!! Great location!!"
United States
Doug Y.
The price is AED 562
AED 1,353 total
includes taxes & fees
21 Dec - 22 Dec
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Classic Room, 1 Queen Bed, Balcony, Pool View (1) | Balcony view
Curry House

Curry House

Curry House
2.0 star property
Old Town Key West
7.2 out of 10, Good, (45)
"This was a great older home with an amazing location to all the action on Duval. Seriously considering heading back next weekend for my Wife's B-Day! "
United States
Steven
Curry House
King Suite Pool View | Iron/ironing board, free WiFi, bed sheets
Kona Kai Oasis

Kona Kai Oasis

Kona Kai Oasis
3.0 star property
Old Town Key West
8.2 out of 10, Very Good, (588)
"It’s soo beautiful place to stay and everything is nearby "
United States
Murali sai tejeswar
Kona Kai Oasis
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 Sugarloaf Key Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"It’s was great!"
Mitchell 5-night trip
Posted 1 day ago
Winslow's Bungalows - Key West Historic Inns