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 1672 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 Pier House Resort & Spa .

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

Expedia has 1672 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, Ernest Hemingway Home and Museum and Florida Keys Eco - Discovery Center 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 Red Barn Theater, Key West Film Society and The Key West Theater.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Jackson Square hotels

A tropical outdoor area with palm trees, hanging plants, and string lights.

1. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

Maricela

฿6,907 total

includes taxes & fees

28 Oct - 29 Oct

A pool area with lounge chairs and a table, surrounded by palm trees.

2. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

ben

฿8,906 total

includes taxes & fees

2 Nov - 3 Nov

A gated entrance to Villas Key West with a brick pathway leading to the gate.

3. Key West Villas

Downtown Key West, 0.3 km from Jackson Square

Margaret

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

4. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Gisele

฿8,504 total

includes taxes & fees

28 Oct - 29 Oct

A modern interior with a staircase, a sofa set, a wooden table, and a television.

5. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.4 km from Jackson Square

William

฿7,562 total

includes taxes & fees

28 Oct - 29 Oct

A two-story house with a covered porch, a brick pathway, and a large tree.

6. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Josh

฿18,986 total

includes taxes & fees

10 Nov - 11 Nov

A porch with a white railing, a bench, and a flag.

7. The Conch House Heritage Inn

Old Town Key West, 0.7 km from Jackson Square

Jennifer

฿11,760 total

includes taxes & fees

28 Oct - 29 Oct

A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

8. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Elise

฿7,521 total

includes taxes & fees

2 Nov - 3 Nov

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

9. Duval House

Downtown Key West, 0.4 km from Jackson Square

Cathrine

฿5,628 total

includes taxes & fees

29 Oct - 30 Oct

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

10. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Justyn

฿6,745 total

includes taxes & fees

28 Oct - 29 Oct

A pool area with lounge chairs and palm trees.

11. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

Anthony

฿13,642 total

includes taxes & fees

28 Oct - 29 Oct

A room with a bed, a ceiling fan, and a window with blinds.

12. The Mermaid & Alligator

Old Town Key West, 0.8 km from Jackson Square

Adam

฿12,991 total

includes taxes & fees

25 Nov - 26 Nov

A large, ornate hotel with a pool, palm trees, and a view of the ocean.

13. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

Janet

฿12,223 total

includes taxes & fees

10 Nov - 11 Nov

A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.

14. Westwinds Inn

Historic Seaport, 0.8 km from Jackson Square

Shari

฿11,110 total

includes taxes & fees

22 Nov - 23 Nov

A gated entrance with lush green foliage and a white picket fence.

15. Coco Plum Inn

Downtown Key West, 0.1 km from Jackson Square

August

฿6,820 total

includes taxes & fees

28 Oct - 29 Oct

A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

16. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

RICHARD

฿6,333 total

includes taxes & fees

28 Oct - 29 Oct

A poolside area with lounge chairs, umbrellas, and a pergola.

17. Ella's Cottages - Key West Historic Inns

Old Town Key West, 0.5 km from Jackson Square

Lisa and David

฿11,206 total

includes taxes & fees

29 Oct - 30 Oct

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

18. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

sam

฿6,863 total

includes taxes & fees

28 Oct - 29 Oct

A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.

19. Alexander Palms Court

Casa Marina, 1.2 km from Jackson Square

Brenda

฿5,436 total

includes taxes & fees

28 Oct - 29 Oct

A covered porch with white railings, wooden benches, and a hanging light fixture.

20. Marrero's Guest Mansion

Downtown Key West, < 0.1 km from Jackson Square

Michael

฿15,352 total

includes taxes & fees

10 Nov - 11 Nov

View all properties

Compare popular hotels close to Jackson Square

Property	Property class	Guest rating
Douglas House - Adults Only	3.0 star property	9.8 Exceptional 569 reviews	View
Orchid Key Inn - Adults Only	3.5 star property	9.8 Exceptional 1,003 reviews	View
Key West Villas	3.5 star property	9.8 Exceptional 279 reviews	View
The Gardens Hotel	4.0 star property	9.8 Exceptional 1,000 reviews	View
Simonton Court Historic Inn & Cottages	2.5 star property	9.8 Exceptional 1,001 reviews	View

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Wonderful stay all around!"

Coco Plum Inn

10/10 Excellent

"We thoroughly enjoyed our stay. Including up-front communication through every interaction during our visit, we loved the Coco Plum from start to finish. Perfect for a simple, comfortable, and relaxing weekend trip - our first visit together to Key West, though we are frequent domestic and global travelers. We like quality, not glitz. This place delivers what we want and honest value at a very affordable price. Easy walking to all the sites and restaurants and the pool was a calm oasis from the heat and humidity and hubbub. Like the friendly reception, big bathroom, comfortable bed, fridge in the room, and ice machine outside by the pool, and especially when you add a decent hot breakfast and good coffee to the mix - there is no better recipe for dialing up a nice rest in Key West. We say this after two days and nights of walking in every direction (not to mention the very reasonable parking across the street) Bravo, Coco Plum!"

Tranquility Guest House

10/10 Excellent

"We arrived to the cutest guest houses the abundance of tropical foliage and brick landscaping we’re so welcoming the pool was a bit chilly with the trees over head but it was clean and still enjoyable. The lounge chairs were free the whole time and we didn’t expect the coffee service in the morning but it was a delightful surprise. The room… modern industrial nicer than a few of the big corp hotels nearby! Bed was soo comfortable ac worked great our tv didn’t work but I didn’t come to watch tv soo didn’t care. Easy 2 block walk to the Duvall st food/bars & entertainment !! We only stayed two nights but they were the best nights of our week! If I had to list something I didn’t like it would be how often the roosters woke us up before we were ready to get up. Honestly would stay here over many other locations"

Other attractions near Jackson Square

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 cycling. If you're looking for a convenient place to stay, take a look at the 1672 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 Pier House Resort & Spa.

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

Expedia has 1672 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, Ernest Hemingway Home and Museum and Florida Keys Eco - Discovery Center 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 Red Barn Theater, Key West Film Society and The Key West Theater.

Search Hotels Near Jackson Square, Key West

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Jackson Square hotels

1. Douglas House - Adults Only

2. Orchid Key Inn - Adults Only

3. Key West Villas

4. The Gardens Hotel

5. Simonton Court Historic Inn & Cottages

6. The Marquesa Hotel

7. The Conch House Heritage Inn

8. Island City House Hotel

9. Duval House

10. The Grand Guesthouse

11. Santa Maria Suites

12. The Mermaid & Alligator

13. Southernmost House - Adult Exclusive

14. Westwinds Inn

15. Coco Plum Inn

16. Ambrosia Key West

17. Ella's Cottages - Key West Historic Inns

18. Silver Palms Inn & Historic Homes

19. Alexander Palms Court

20. Marrero's Guest Mansion

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

Other attractions near Jackson Square

San Carlos Institute - Casa Cuba

Frequently asked questions