The Best Hotels Closest to Jackson Square in Key West for 2026

Q: 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 1722 hotels and other accommodations you'll find within a mile.

Q: 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 Hyatt Centric Key West Resort and Spa .

Q: How many hotels will I be able to find close to Jackson Square?

Expedia has 1722 hotels and other accommodations within a mile from Jackson Square.

Q: 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.

Q: Where can I learn more about changing or cancelling my trip in the area near Jackson Square?

For more information about updating your stay near Jackson Square or cancelling it, click here .

Q: 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, Fort Zachary Taylor Historic State Park, and Curry Mansion Museum 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.

Our top choices for Jackson Square hotels

The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Joseph

₩344,065 total

includes taxes & fees

Jul 12 - Jul 13

Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Almond Tree Inn Hotel - Adults Only

Downtown Key West, 0.6 km from Jackson Square

Jimmy

₩292,197 total

includes taxes & fees

Jun 30 - Jul 1

Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished

Simonton Court Historic Inn & Cottages

Historic Seaport, 0.4 km from Jackson Square

Rita

₩292,196 total

includes taxes & fees

Jun 28 - Jun 29

Artist House Key West

Historic Seaport, 0.3 km from Jackson Square

NATHAN

₩226,933 total

includes taxes & fees

Jun 30 - Jul 1

The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Helia

₩439,465 total

includes taxes & fees

Jul 8 - Jul 9

Key West Villas

Downtown Key West, 0.3 km from Jackson Square

Jennifer

₩354,919 total

includes taxes & fees

Jun 29 - Jun 30

Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

Michael

₩335,793 total

includes taxes & fees

Jun 24 - Jun 25

11 Gecko's Garden - Adults Only | Premium bedding, pillowtop beds, individually decorated

Tropical Inn

Downtown Key West, 0.4 km from Jackson Square

Akhenaton

₩311,814 total

includes taxes & fees

Jun 25 - Jun 26

L'Habitation Guest House

Historic Seaport, 0.2 km from Jackson Square

Richard

₩216,313 total

includes taxes & fees

Jun 28 - Jun 29

Coco Plum Inn

Downtown Key West, 0.1 km from Jackson Square

Brinkley

₩318,305 total

includes taxes & fees

Jun 29 - Jun 30

Marrero's Guest Mansion

Downtown Key West, < 0.1 km from Jackson Square

Robert

₩344,072 total

includes taxes & fees

Jun 29 - Jun 30

Cigar House King Suite w/ Poolside porch | Balcony view

Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

₩299,682 total

includes taxes & fees

Jun 24 - Jun 25

Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

Matthew

₩163,561 total

includes taxes & fees

Jul 20 - Jul 21

Duval House

Downtown Key West, 0.4 km from Jackson Square

Wendy S

₩237,829 total

includes taxes & fees

Jul 5 - Jul 6

Premium bedding, iron/ironing board, free WiFi, bed sheets

Weatherstation Inn

Truman Annex, 0.3 km from Jackson Square

Bret

₩309,485 total

includes taxes & fees

Jun 29 - Jun 30

The Conch House Heritage Inn

Old Town Key West, 0.7 km from Jackson Square

Lucy

₩409,151 total

includes taxes & fees

Jun 28 - Jun 29

3 outdoor pools, a heated pool, sun loungers

Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Lori

₩278,280 total

includes taxes & fees

Jul 1 - Jul 2

Heron House - Adult Only

Downtown Key West, 0.3 km from Jackson Square

Cameron

₩271,643 total

includes taxes & fees

Jun 28 - Jun 29

Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave | Free WiFi, bed sheets

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Old Town Key West, 1.1 km from Jackson Square

Annette

₩465,037 total

includes taxes & fees

Jun 24 - Jun 25

Deluxe Suite, 1 King Bed, Private Pool | View from room

H2O Suites - Adults Only

Uptown - Upper Duval, 1 km from Jackson Square

Elizabeth

₩721,524 total

includes taxes & fees

Jul 8 - Jul 9

View all properties

Compare popular hotels close to Jackson Square

Property	Property class	Guest rating
The Gardens Hotel	4.0 star property	9.8 Exceptional 1,001 reviews	View
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,003 reviews	View
Simonton Court Historic Inn & Cottages	2.5 star property	9.8 Exceptional 989 reviews	View
Artist House Key West	3.5 star property	9.8 Exceptional 442 reviews	View
The Marquesa Hotel	3.5 star property	9.8 Exceptional 1,001 reviews	View

Top Jackson Square Hotel Reviews

Duval House

10/10 Excellent

"I loved this place… great location!"

Heron House - Adult Only

8/10 Good

"I found the property well maintained, comfortable and easy to access. The location was great. Next time I will request a room on the second floor simply because our upstairs neighbors were really heavy walkers. Additionally, we were charged an additional $60 resort fee when we checked out and the only amenity was the pool. I didn't love having to pay extra for it, especially because we didn't use it."

Simonton Court Historic Inn & Cottages

10/10 Excellent

"I rarely review places but when I do they deserve it! Simonton Court was top notch. We got a good price for the stay. We arrived to find an inviting flower covered, palm lined inviting walkway. They upgraded us to a king size bed, but that was 3rd floor so we chose to stay in our queen on the first floor. The little houses would have been perfect to stay in. Pools were nice, place clean, breakfast nice, hoped for omelets. Located 1 block from Duval St in the center of everything but far enough for it to be quiet. But all in all I rate our Stay a 9 out of 10,"

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

8.6/5 (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 1722 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 Hyatt Centric Key West Resort and Spa.

How many hotels will I be able to find close to Jackson Square?

Expedia has 1722 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.

Where can I learn more about changing or cancelling my trip in the area near Jackson Square?

For more information about updating your stay near Jackson Square or cancelling it, click here.

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, Fort Zachary Taylor Historic State Park, and Curry Mansion Museum 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.

Find hotels near Jackson Square, Key West from ₩163,561

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Our top choices for Jackson Square hotels

The Gardens Hotel

Almond Tree Inn Hotel - Adults Only

Simonton Court Historic Inn & Cottages

Artist House Key West

The Marquesa Hotel

Key West Villas

Orchid Key Inn - Adults Only

Tropical Inn

L'Habitation Guest House

Coco Plum Inn

Marrero's Guest Mansion

Island City House Hotel

Douglas House - Adults Only

Duval House

Weatherstation Inn

The Conch House Heritage Inn

Ambrosia Key West

Heron House - Adult Only

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

H2O Suites - Adults Only

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Duval House

Hotels near other Jackson Square attractions

San Carlos Institute - Casa Cuba

Frequently asked questions