The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

Hotels near Jackson Square

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Check prices for these dates

This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

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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, (1,002 reviews)
"Excellent accommodations"
United States
Jimmy
The price is P13,709
P15,422 total
includes taxes & fees
Jul 6 - Jul 7
Almond Tree Inn Hotel - Adults Only
Restaurant

Artist House Key West

Artist House Key West
3.5 star property
Historic Seaport, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (444 reviews)
"Great atmosphere and location."
United States
NATHAN
The price is P8,928
P10,045 total
includes taxes & fees
Jul 19 - Jul 20
Artist House Key West
Exterior detail

The Gardens Hotel

The Gardens Hotel
4.0 star property
Downtown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,004 reviews)
"Whole place is great"
United States
Joseph
The price is P12,174
P13,696 total
includes taxes & fees
Jul 12 - Jul 13
The Gardens Hotel
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, (993 reviews)
"Perfcet location and walk to everything , we very much enjoyed our stay!"
United States
Rita
The price is P8,503
P9,566 total
includes taxes & fees
Jul 1 - Jul 2
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, (1,000 reviews)
"Friendly and helpful staff, and the rooms were exceptionally clean and comfortable. Everything was well-maintained, and the overall experience was wonderful. I will definitely be coming back again!"
United States
Helia
The price is P14,337
P19,570 total
includes taxes & fees
Jul 21 - Jul 22
The Marquesa Hotel
Front of property

Key West Villas

Key West Villas
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (264 reviews)
"This was the best place we have stayed at in Key West! It was super quiet but only a block from Duval. The owners really put a lot of care into the place and are super nice! Definitely would stay there again! "
United States
Jennifer
The price is P12,608
P14,185 total
includes taxes & fees
Jul 5 - Jul 6
Key West Villas
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, (1,002 reviews)
"Great boutique hotel in the perfect location !! "
United States
Michael
The price is P12,923
P14,539 total
includes taxes & fees
Jul 1 - Jul 2
Orchid Key Inn - Adults Only
Exterior

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (539 reviews)
"Loved the property and staff was super friendly."
United States
Brinkley
The price is P10,767
P12,113 total
includes taxes & fees
Jul 1 - Jul 2
Coco Plum Inn
Terrace/patio

The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West, 0.7 km from Jackson Square
9.8 out of 10, Exceptional, (177 reviews)
"Great location "
United Kingdom
Lucy
The price is P13,067
P14,700 total
includes taxes & fees
Jul 13 - Jul 14
The Conch House Heritage Inn
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, (998 reviews)
"Loved the location, breakfast and clean room. Staff, Drew, very friendly and helpful. Will definitely stay here again."
United States
Richard
The price is P7,118
P8,008 total
includes taxes & fees
Jul 6 - Jul 7
L'Habitation Guest House
Premium bedding, pillowtop beds, individually decorated

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (414 reviews)
"Very friendly staff and a prime location."
United States
Akhenaton
The price is P9,312
P12,005 total
includes taxes & fees
Jul 1 - Jul 2
Tropical Inn
Balcony view

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, (1,002 reviews)
"I love this Hotel. Great location, safe m, convenient. The staff is very accommodating."
United States
Paul
The price is P11,376
P12,798 total
includes taxes & fees
Jul 1 - Jul 2
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, (435 reviews)
"Great stay"
United States
Matthew
The price is P5,273
P6,525 total
includes taxes & fees
Jul 20 - Jul 21
Douglas House - Adults Only
Terrace/patio

Marrero's Guest Mansion

Marrero's Guest Mansion
3.5 star property
Downtown Key West, < 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (337 reviews)
"Service and hospitality were exceptional. Will stay again. "
United States
Don
The price is P12,174
P13,696 total
includes taxes & fees
Jul 21 - Jul 22
Marrero's Guest Mansion
Terrace/patio

The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West, 0.8 km from Jackson Square
9.8 out of 10, Exceptional, (305 reviews)
"Great location, lovely place, clean and comfortable room. Highly recommend! "
United States
Mary
The price is P13,367
P15,038 total
includes taxes & fees
Jul 6 - Jul 7
The Mermaid & Alligator
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, (1,005 reviews)
"Quaint place to stay with access to there other more resort style property made for an amazing experience."
United States
Bret
The price is P10,950
P12,319 total
includes taxes & fees
Jul 5 - Jul 6
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, (1,004 reviews)
"Great location and breakfast"
United States
Lori
The price is P9,886
P11,122 total
includes taxes & fees
Jul 1 - Jul 2
Ambrosia Key West
Property grounds

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,045 reviews)
"Great location and clean rooms. Breakfast staff is so sweet! Will stay here again for sure!!"
United States
Wendy S
The price is P6,683
P8,836 total
includes taxes & fees
Jul 1 - Jul 2
Duval House
Porch

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, (1,164 reviews)
"Hotel was amazing and breakfast was delicious!"
United States
Cameron
The price is P7,260
P10,207 total
includes taxes & fees
Jul 5 - Jul 6
Heron House - Adult Only
Free WiFi, bed sheets

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
3.5 star property
Old Town Key West, 1.1 km from Jackson Square
9.8 out of 10, Exceptional, (149 reviews)
"The staff and other guests were very friendly. The room was spacious and the bed was comfortable. "
United States
Annette
The price is P6,552
P9,697 total
includes taxes & fees
Jul 1 - Jul 2
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
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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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
1,002 reviews
View
Restaurant
Artist House Key West
3.5 star property
9.8
Exceptional
444 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,004 reviews
View
Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
993 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,000 reviews
View

Top Jackson Square Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

8/10 Good
"We had a great time, the staff were so friendly and helpful. The one downside was the price for our suite was a little ridiculous for what the room really was. Our suite was very small with no view. Most hotels we stay at have bigger / nicer rooms for the price."
Anthony 2-night trip
Posted 1 hour ago
Pier House Resort & Spa

Hotels near other Jackson Square attractions

A historic building with ornate architecture, a balcony, and a coat of arms.

San Carlos Institute - Casa Cuba

8.6/10 (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 1718 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, La Concha Key West, Autograph Collection is one of the top choices for your stay based on our traveler data, and this hotel offers 3 restaurants and 2 bars. Other good options close by include Southernmost Beach Resort and Guesthouses and Pier House Resort & Spa.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1718 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 Ernest Hemingway Home and Museum feature a variety of fascinating exhibits to see while you're in town. Key West Lighthouse and Keeper's Quarters Museum, Key West Historic Seaport, 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.