The Best Hotels Closest to Jackson Square in Key West - 2026 Updated Prices

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 cycling. If you're looking for a convenient place to stay, take a look at the 1722 hotels and other accommodation options you'll find within a mile.

Q: 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 Hyatt Centric Key West Resort and Spa .

Q: How many hotels can I expect to find close to Jackson Square?

Expedia has 1722 hotels and other accommodation options 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, 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.

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 Fort East Martello Museum and Gallery 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

1. Key West Villas

Downtown Key West, 0.3 km from Jackson Square

Jennifer

Rp4.141.198 total

includes taxes & fees

16 Jun - 17 Jun

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

2. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.4 km from Jackson Square

Francis

Rp2.993.783 total

includes taxes & fees

16 Jun - 17 Jun

Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

3. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 0.6 km from Jackson Square

Jimmy

Rp4.022.518 total

includes taxes & fees

15 Jun - 16 Jun

4. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Joseph

Rp4.802.107 total

includes taxes & fees

28 Jun - 29 Jun

5. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Julian

Rp6.610.522 total

includes taxes & fees

21 Jun - 22 Jun

6. The Conch House Heritage Inn

Old Town Key West, 0.7 km from Jackson Square

Lucy

Rp4.773.978 total

includes taxes & fees

14 Jun - 15 Jun

7. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

Michael

Rp3.891.918 total

includes taxes & fees

15 Jun - 16 Jun

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

8. Tropical Inn

Downtown Key West, 0.4 km from Jackson Square

Akhenaton

Rp3.030.842 total

includes taxes & fees

15 Jun - 16 Jun

Cigar House King Suite w/ Poolside porch | Balcony view

9. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Troy

Rp3.443.453 total

includes taxes & fees

14 Jun - 15 Jun

10. Marrero's Guest Mansion

Downtown Key West, < 0.1 km from Jackson Square

Robert

Rp4.701.645 total

includes taxes & fees

17 Jun - 18 Jun

11. L'Habitation Guest House

Historic Seaport, 0.2 km from Jackson Square

Richard

Rp2.540.228 total

includes taxes & fees

15 Jun - 16 Jun

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

12. Weatherstation Inn

Truman Annex, 0.3 km from Jackson Square

Bret

Rp3.596.558 total

includes taxes & fees

14 Jun - 15 Jun

13. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

Matthew

Rp2.751.529 total

includes taxes & fees

15 Jun - 16 Jun

14. Heron House - Adult Only

Downtown Key West, 0.3 km from Jackson Square

Renee Louise

Rp3.199.976 total

includes taxes & fees

14 Jun - 15 Jun

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

15. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Old Town Key West, 1.1 km from Jackson Square

Annette

Rp4.313.904 total

includes taxes & fees

14 Jun - 15 Jun

16. Westwinds Inn

Historic Seaport, 0.8 km from Jackson Square

michael

Rp3.707.066 total

includes taxes & fees

15 Jun - 16 Jun

3 outdoor pools, a heated pool, pool loungers

17. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Lori

Rp3.590.556 total

includes taxes & fees

14 Jun - 15 Jun

18. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Duncan

Rp2.990.230 total

includes taxes & fees

14 Jun - 15 Jun

Outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

19. Ella's Cottages - Key West Historic Inns

Old Town Key West, 0.5 km from Jackson Square

Nanci

Rp4.986.042 total

includes taxes & fees

1 Jul - 2 Jul

20. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

Jennifer

Rp3.267.130 total

includes taxes & fees

15 Jun - 16 Jun

View all properties

Compare popular hotels close to Jackson Square

Property	Property class	Guest rating
Key West Villas	3.5 star property	9.8 Exceptional 262 reviews	View
Simonton Court Historic Inn & Cottages	2.5 star property	9.8 Exceptional 982 reviews	View
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,016 reviews	View
The Gardens Hotel	4.0 star property	9.8 Exceptional 1,007 reviews	View
The Marquesa Hotel	3.5 star property	9.8 Exceptional 1,001 reviews	View

Top Jackson Square Hotel Reviews

Heron House - Adult Only

10/10 Excellent

"Perfect and quiet escape just off of duval. Walking distance from all the main places. We will definitely be back!"

Coco Plum Inn

8/10 Good

"For the most part, it was very clean. Rooms were well kept up with the pool area is absolutely magical very beautiful. The breakfast in the morning is very cute and romantic. Only downside to our stay is the plumbing was not great three out of the six days we were there we had to go around the corner to a bar to go to the bathroom because the toilet wouldn’t flush, but that’s the only flaw everything else was beautiful my husband and I loved it. I will return and if you’re looking for AC, they have the coldest rooms and it’s so refreshing after a hot day and the hotel manager is so awesome and so friendly."

Duval House

10/10 Excellent

"Loved our stay here. Upon arrival we were offered complimentary drinks and check in was a breeze. Our room was so coxy and clean. The grounds were like being in a tropical Paradise! Everything was perfect. Right on Duvall Street and we walked everywhere. Plenty of restsurants and bars. We tried several restaurants, but our fav was Havana Island Cafe (I think). Had to enter through an alley. It was a food truck with a bar and the BEST food. Highly recommend!! We did the hop on/hop off tour our 1st full day and I wished we had just rented a golf cart, which we did for the remainder of our trip. Breakfast was awesome. The best waffles and the staff were so nice. It was a bucket list trip for me and I was not disappointed. Everyone should visit Key West and stay at the Duval House!!!"

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 cycling. If you're looking for a convenient place to stay, take a look at the 1722 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 Hyatt Centric Key West Resort and Spa.

How many hotels can I expect to find close to Jackson Square?

Expedia has 1722 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, Fort Zachary Taylor Historic State Park and Fort East Martello Museum and Gallery 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.

Search Hotels Near Jackson Square, Key West

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Our top choices for Jackson Square hotels

1. Key West Villas

2. Simonton Court Historic Inn & Cottages

3. Almond Tree Inn Hotel - Adults Only

4. The Gardens Hotel

5. The Marquesa Hotel

6. The Conch House Heritage Inn

7. Orchid Key Inn - Adults Only

8. Tropical Inn

9. Island City House Hotel

10. Marrero's Guest Mansion

11. L'Habitation Guest House

12. Weatherstation Inn

13. Douglas House - Adults Only

14. Heron House - Adult Only

15. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

16. Westwinds Inn

17. Ambrosia Key West

18. The Grand Guesthouse

19. Ella's Cottages - Key West Historic Inns

20. Silver Palms Inn & Historic Homes

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Heron House - Adult Only

Hotels near other Jackson Square attractions

San Carlos Institute - Casa Cuba

Frequently asked questions