Hotels near Jackson Square

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Check prices for these dates

Next weekend
May 22 - May 24
In two weeks
May 29 - May 31

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Our top choices for Jackson Square hotels

Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
3.5 star property
Downtown Key West, 0.6 km from Jackson Square
10.0 out of 10, Exceptional, (1,013 reviews)
"Great staff, breakfast and happy hour. "
United States
Tina
The price is P17,131
P19,272 total
includes taxes & fees
May 20 - May 21
Almond Tree Inn Hotel - Adults Only
Minibar, in-room safe, individually decorated, individually furnished

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Historic Seaport, 0.4 km from Jackson Square
9.8 out of 10, Exceptional, (953 reviews)
"Defiantly would stay again and so close to everything"
United States
kelly
The price is P15,349
P17,267 total
includes taxes & fees
May 20 - May 21
Simonton Court Historic Inn & Cottages
Exterior

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,005 reviews)
"Great accommodations and great staff"
United States
Julian
The price is P17,838
P23,540 total
includes taxes & fees
Jun 16 - Jun 17
The Marquesa Hotel
Property grounds

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Uptown - Upper Duval, 0.6 km from Jackson Square
9.8 out of 10, Exceptional, (1,004 reviews)
"This is an amazing place ! If you are coming to Key West you won’t find a nicer place. "
United States
Vicki
The price is P15,647
P17,602 total
includes taxes & fees
May 21 - May 22
Orchid Key Inn - Adults Only
Front of property

Island City House Hotel

Island City House Hotel
3.0 star property
Historic Seaport, 0.6 km from Jackson Square
9.6 out of 10, Exceptional, (1,000 reviews)
"Nice location "
United States
Michael
The price is P14,351
P16,145 total
includes taxes & fees
Jun 2 - Jun 3
Island City House Hotel
Exterior

Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Uptown - Upper Duval, 0.8 km from Jackson Square
9.6 out of 10, Exceptional, (385 reviews)
"Great location, helpful staff and fun people. Would stay here again…the pool and room were fantastic"
United States
Scott
The price is P11,067
P13,696 total
includes taxes & fees
Jun 2 - Jun 3
Douglas House - Adults Only
Front of property

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Historic Seaport, 0.2 km from Jackson Square
9.4 out of 10, Exceptional, (981 reviews)
"This was a lovely well stocked, and comfortable stay."
United States
Pat
The price is P9,943
P11,187 total
includes taxes & fees
May 20 - May 21
L'Habitation Guest House
View from room

H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Uptown - Upper Duval, 1 km from Jackson Square
9.8 out of 10, Exceptional, (604 reviews)
"This resort was in the perfect location for exploring Key West. Highly recommend!"
United States
Barton
The price is P22,158
P29,094 total
includes taxes & fees
Jun 2 - Jun 3
H2O Suites - Adults Only
Courtyard

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,040 reviews)
"Nice place clean, good breakfast right on Duval for easy walk to everything "
Canada
Parmjit
The price is P11,604
P14,381 total
includes taxes & fees
May 31 - Jun 1
Duval House
Premium bedding, iron/ironing board, free WiFi, bed sheets

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (1,001 reviews)
"Perfect stay!"
United States
A. Elise
The price is P12,283
P13,818 total
includes taxes & fees
May 19 - May 20
Weatherstation Inn
3 outdoor pools, a heated pool, sun loungers

Ambrosia Key West

Ambrosia Key West
3.5 star property
Old Town Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,000 reviews)
"Breakfast by the pool was excellent! Pools were nice, with plenty of areas for privacy. We especially enjoyed the private patios and courtyards. Fantastic location!"
United States
Tina
The price is P13,141
P14,783 total
includes taxes & fees
May 17 - May 18
Ambrosia Key West
Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
3.5 star property
Old Town Key West, 0.5 km from Jackson Square
9.4 out of 10, Exceptional, (475 reviews)
"Cute place. Great location to everything on Duval. Service was great and friendly."
United States
DJS Darren Jay
The price is P11,610
P16,186 total
includes taxes & fees
May 27 - May 28
Ella's Cottages - Key West Historic Inns
Lobby sitting area

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.8 km from Jackson Square
9.4 out of 10, Exceptional, (1,018 reviews)
"Very clean rooms staff was very helpful. Pools we’re nice little small you continental breakfast could add a couple more things like bananas all in all 10 out of 10"
United States
Bruce
The price is P14,701
P16,539 total
includes taxes & fees
Jun 2 - Jun 3
Westwinds Inn
View from room

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (1,147 reviews)
"Wonderful stay! Loved the property and location. "
United States
Janet
The price is P8,579
P11,745 total
includes taxes & fees
May 17 - May 18
Heron House - Adult Only
Courtyard

The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,001 reviews)
"This is a great place to stay, quiet and nice accommodations. Awesome little courtyard for breakfast."
United States
Jacqueline
The price is P9,082
P11,760 total
includes taxes & fees
May 18 - May 19
The Grand Guesthouse
Outdoor pool

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1,041 reviews)
"Great continental breakfast options. Onsite parking was convenient."
United States
Keith
The price is P7,157
P12,212 total
includes taxes & fees
May 25 - May 26
Silver Palms Inn & Historic Homes
2 outdoor pools, sun loungers

Santa Maria Suites

Santa Maria Suites
4.0 star property
Uptown - Upper Duval, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,006 reviews)
"Great hotel and room. Very clean, great location."
United States
Cindy
The price is P19,047
P25,589 total
includes taxes & fees
May 27 - May 28
Santa Maria Suites
Outdoor pool

The Key West Hotel

The Key West Hotel
3.0 star property
Historic Seaport, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (553 reviews)
"Great location"
United States
David
The price is P21,069
P27,093 total
includes taxes & fees
Jun 3 - Jun 4
The Key West Hotel
Exterior

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
3.5 star property
Historic Seaport, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (908 reviews)
"Staff was amazing from check in to check out. Located in a great location, close to everything but far enough its not loud while sleeping."
United States
Brennan
The price is P13,239
P18,019 total
includes taxes & fees
May 28 - May 29
Ridley House - Key West Historic Inns
Front of property - evening/night

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (1,099 reviews)
"Amazing stay.. will definitely be back!!!"
United States
Jennifer
The price is P15,986
P20,415 total
includes taxes & fees
May 25 - May 26
Opal Key Resort & Marina, Key West
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

Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,013 reviews
View
Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
953 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,005 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,004 reviews
View
Front of property
Island City House Hotel
3.0 star property
9.6
Exceptional
1,000 reviews
View

Top Jackson Square Hotel Reviews

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"This trip makes number 17!! La Concha number 5! This place has proven to be the spot to stay when in Key West. The remodel is amazing! Parking ?? Perfect! Location to EVERYTHING?! PERFECT! Love the rooftop pool and bar! Room stayed a crispy 62! If you come to KW and don't stay here it is UOUR faul you didn't!! Love this place!!"
Scot 3-night trip
Posted 3 hours ago
La Concha Key West, Autograph Collection

Hotels near other Jackson Square attractions

KEY WEST, FLORIDA, USA - September 2012: San Carlos institute is a historic Key West building also known as "La casa de Cuba"

San Carlos Institute - Casa Cuba

4.3/5 (34 reviews)
You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's beautiful beaches or experience its lively festivals.
See properties

Frequently asked questions

What's the area like around Jackson Square?
Jackson Square is located in an area of Key West known for its beautiful ocean views, bar scene, and biking. If you're looking for a convenient place to stay, check out the 1734 hotels and other accommodations you'll find within a mile.
Where is the best place to stay close to Jackson Square?
Adjacent to Jackson Square, The Cabana Inn Key West - Adults Only is one of the top choices for your stay based on our traveler data, and this guesthouse offers free breakfast and an outdoor pool. Other good options close by include Southernmost Beach Resort and Guesthouses and Opal Key Resort & Marina, Key West.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1734 hotels and other accommodations within a mile from Jackson Square.
If I need to cancel the hotel reservation for my stay near Jackson Square, will I receive a refund?
Yes! The majority of hotel bookings are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to review the best deals near Jackson Square.
What can I see and do near Jackson Square?
Harry S. Truman Little White House, Audubon House and Tropical Gardens, and Mel Fisher Maritime Museum feature a variety of fascinating exhibits to see while you're in town. Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum, and Fort Zachary Taylor Historic State Park are some of the local landmarks to explore. You can check out the local talent at Waterfront Playhouse, Key West Film Society, and Red Barn Theater.