Top Hotels Near Jackson Square in Key West from NZ$493

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Jackson Square hotels

Queen Deluxe ADA
Almond Tree Inn Hotel - Adults Only

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, (1002)
"Great location, spotless rooms, attentive and friendly staff, great value."
United States
David
The price is NZ$762
includes taxes & fees
6 Jan - 7 Jan 2026
Almond Tree Inn Hotel - Adults Only
Queen with Pool View
Simonton Court Historic Inn & Cottages

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, (883)
"The staff was really nice"
United States
doug
The price is NZ$774
includes taxes & fees
6 Jan - 7 Jan 2026
Simonton Court Historic Inn & Cottages
Front of property
Key West Villas

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, (247)
"Awsome staff great location "
United States
Jeffrey
Key West Villas
Exterior
The Marquesa Hotel

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Historic Seaport, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1000)
"Perfect place to stay. "
United States
Paulette
The price is NZ$1,288
includes taxes & fees
12 Jan - 13 Jan 2026
The Marquesa Hotel
Exterior detail
The Gardens Hotel

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, (1002)
"Loved it. The staff were very friendly and the place was classic Key West."
United States
Ben
The price is NZ$943
includes taxes & fees
24 Dec - 25 Dec
The Gardens Hotel
Property grounds
Orchid Key Inn - Adults Only

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, (1003)
"Staff awesome, good breakfast great location"
United States
Carin helen
The price is NZ$754
includes taxes & fees
6 Jan - 7 Jan 2026
Orchid Key Inn - Adults Only
Veranda Room | Terrace/patio
The Conch House Heritage Inn

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, (145)
"Fantastic location "
United States
ANDREW
The price is NZ$646
includes taxes & fees
4 Jan - 5 Jan 2026
The Conch House Heritage Inn
Audubon Room - Adult Exclusive | Terrace/patio
The Mermaid & Alligator

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, (275)
"Great place"
United States
Carol A
The Mermaid & Alligator
Deluxe Suite, 1 King Bed, Private Pool | View from room
H2O Suites - Adults Only

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, (582)
"Great place!!"
United States
Joel
The price is NZ$1,085
includes taxes & fees
4 Jan - 5 Jan 2026
H2O Suites - Adults Only
Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

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, (134)
"We absolutely loved finding this gem to stay on our first visit to Key West. Great location, wonderful staff, and excellent room. "
United States
Sammy
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Exterior
Coco Plum Inn

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.1 km from Jackson Square
9.6 out of 10, Exceptional, (468)
"Love the place convenient, clean and really nice"
United States
Matthew
The price is NZ$614
includes taxes & fees
24 Dec - 25 Dec
Coco Plum Inn
11 Gecko's Garden - Adults Only
Tropical Inn

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (364)
"Nice place to stay "
United States
yulio
The price is NZ$694
includes taxes & fees
4 Jan - 5 Jan 2026
Tropical Inn
Cigar House King Suite w/ Poolside porch | Balcony view
Island City House Hotel

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, (1003)
"Excellent stay"
United States
Emily Barbara
The price is NZ$783
includes taxes & fees
11 Jan - 12 Jan 2026
Island City House Hotel
Courtyard
The Grand Guesthouse

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, (1001)
"Great stay"
United States
Ginger
The price is NZ$681
includes taxes & fees
24 Dec - 25 Dec
The Grand Guesthouse
2 outdoor pools, pool loungers
Santa Maria Suites

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, (1001)
"Awesome place we loved it"
United States
Josh
The price is NZ$1,130
includes taxes & fees
13 Jan - 14 Jan 2026
Santa Maria Suites
Front of property
L'Habitation Guest House

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, (924)
"A great no hassle stay."
United States
Gary
The price is NZ$493
includes taxes & fees
5 Jan - 6 Jan 2026
L'Habitation Guest House
Property grounds
Duval House

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1003)
"I loved this place the location was absolutely perfect "
United States
Frank
The price is NZ$520
includes taxes & fees
5 Jan - 6 Jan 2026
Duval House
Premium bedding, iron/ironing board, free WiFi, bed sheets
Weatherstation Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (996)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is NZ$748
includes taxes & fees
6 Jan - 7 Jan 2026
Weatherstation Inn
3 outdoor pools, a heated pool, pool loungers
Ambrosia Key West

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, (1002)
"Great place to stay"
United States
Melody
The price is NZ$592
includes taxes & fees
4 Jan - 5 Jan 2026
Ambrosia Key West
Outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Ella's Cottages - Key West Historic Inns

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, (411)
"The cottage was perfect, centrally located and a wonderful place to stay!"
United States
Claudia
The price is NZ$895
includes taxes & fees
6 Jan - 7 Jan 2026
Ella's Cottages - Key West Historic Inns
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

Top Jackson Square Hotel Reviews

Wicker Guesthouse

Wicker Guesthouse

10/10 Excellent
"Just a lovely stay. Staff was super friendly. available and helpful."
Marilyn 4-night trip
Posted 17 hours ago
Wicker Guesthouse

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

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 seaside or experience its lively festivals.
See properties
Vibrant atmosphere at Duval Street showcases Key West's historic charm and cultural richness in Florida's lively district

Duval Street

4.5/5 (9,716 reviews)
Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.
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 cycling. If you're looking for a convenient place to stay, take a look at the 1795 hotels and other accommodation options you'll find within a mile.
What's the best hotel 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 traveller data, and this hotel offers 3 restaurants and 2 bars. Other good options close by include Hyatt Centric Key West Resort and Spa and The Cabana Inn Key West - Adults Only.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1795 hotels and other accommodation options 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, you'll find most hotel bookings are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Add your dates and click on "Search", then you can filter by "fully refundable" to get the top deals on offer 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 Red Barn Theater, Key West Film Society and Waterfront Playhouse.