Top Hotels Near Jackson Square in Key West from AU$231

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Accommodation near Jackson Square

Queen Deluxe ADA
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 place to stay. "
United States
Bettina
The price is AU$409
includes taxes & fees
10 Dec - 11 Dec
Almond Tree Inn Hotel - Adults Only
King Room D | Balcony
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, (876)
"The staff was really nice"
United States
doug
The price is AU$303
includes taxes & fees
8 Dec - 9 Dec
Simonton Court Historic Inn & Cottages
Carriage House | Terrace/patio
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, (1000)
"Amazing hotel, the perfect Key West vibe. Clean rooms, delicious breakfast. We will come back again"
United States
Isis
The price is AU$551
includes taxes & fees
9 Dec - 10 Dec
The Gardens Hotel
Exterior
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 AU$676
includes taxes & fees
9 Dec - 10 Dec
The Marquesa Hotel
Exterior
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, (1000)
"Great location and amazing staff!"
United States
Charles
The price is AU$403
includes taxes & fees
10 Dec - 11 Dec
Orchid Key Inn - Adults Only
Outdoor pool, pool loungers
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, (144)
"Fantastic location "
United States
ANDREW
The price is AU$326
includes taxes & fees
9 Dec - 10 Dec
The Conch House Heritage Inn
Outdoor pool, pool loungers
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, (271)
"Property had several areas to relax."
United States
Mateo
The Mermaid & Alligator
Deluxe Suite, 1 King Bed, Private Pool | 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, (580)
"Great place!!"
United States
Joel
The price is AU$608
includes taxes & fees
16 Dec - 17 Dec
H2O Suites - Adults Only
Signature Apartment, 1 Bedroom, Kitchen, Poolside (Room 17) | Terrace/patio
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, (129)
"Great place to stay always clean an the employees are very respectful "
United States
Charles
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Exterior
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, (461)
"Overall great for couple's stay. "
United States
Quazi
The price is AU$314
includes taxes & fees
15 Dec - 16 Dec
Coco Plum Inn
Fountain
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, (1000)
"This is the best place to stay near all the waterfront spots but still in the neighborhoods. Nice pool, ice, washer/dryer, great staff - it is so warm n friendly! Would stay again and again!"
United States
Gregory
The price is AU$298
includes taxes & fees
15 Dec - 16 Dec
Island City House Hotel
Garden
Douglas House

Douglas House

3.0 star property
Uptown - Upper Duval, 0.8 km from Jackson Square
9.6 out of 10, Exceptional, (218)
"Very clean room, loved the location!"
United States
Jeffrey Ray
The price is AU$255
includes taxes & fees
17 Dec - 18 Dec
Douglas House
11 Gecko's Garden - Adults Only
Tropical Inn

Tropical Inn

3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (363)
"The place was excellent and the service amazing "
United States
Janae
The price is AU$408
includes taxes & fees
8 Dec - 9 Dec
Tropical Inn
Exterior
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 Grand Guesthouse
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, (919)
"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 AU$231
includes taxes & fees
8 Dec - 9 Dec
L'Habitation Guest 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, (991)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is AU$334
includes taxes & fees
16 Dec - 17 Dec
Weatherstation Inn
3 outdoor pools, a heated pool, pool 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, (1002)
"Great breakfast options, quiet, clean. Walkable where we wanted to go"
United States
Alma D
The price is AU$416
includes taxes & fees
8 Dec - 9 Dec
Ambrosia Key West
Outdoor pool, pool umbrellas, pool loungers
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, (335)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is AU$551
includes taxes & fees
7 Jan - 8 Jan 2026
Marrero's Guest Mansion
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

3.5 star property
Old Town Key West, 0.5 km from Jackson Square
9.4 out of 10, Exceptional, (401)
"Friendly staff, Beautiful property "
United States
Ishta
The price is AU$430
includes taxes & fees
15 Dec - 16 Dec
Ella's Cottages - Key West Historic Inns
Outdoor pool
Silver Palms Inn

Silver Palms Inn

3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1008)
"We had a wonderful stay and it was a convenient location for all the activities along Duval Street. The room was clean & comfortable with a great breakfast."
United States
Susanne
The price is AU$283
includes taxes & fees
16 Dec - 17 Dec
Silver Palms Inn
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 Jackson Square Hotel Reviews

Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"Loved all of it!"
Randy 11-night trip
Posted 1 day ago
Heron House - Adult Only

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.
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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.
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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 1756 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 Southernmost Beach Resort and Guesthouses and Winslow's Bungalows - Key West Historic Inns.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1756 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 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 Key West Historic Seaport are some of the local landmarks to explore. You can check out the local talent at Red Barn Theater, Waterfront Playhouse and Key West Film Society.