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

The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

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Our top choices for Jackson Square hotels

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.

A swimming pool with lounge chairs, surrounded by palm trees and greenery.

A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

A building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 0.6 km from Jackson Square

John

₹27,514

₹30,953 total

includes taxes & fees

15 Oct - 16 Oct

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

A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.

An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.

A large, two-story building with a balcony, surrounded by dense tropical foliage.

2. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

Maricela

₹14,460

₹17,895 total

includes taxes & fees

14 Oct - 15 Oct

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

A patio with a white wicker lounge chair, a wooden table with a book and a potted plant, surrounded by lush tropical foliage and palm trees.

A building with a neon sign that reads "Orchid Key Inn."

A neon sign for Orchid Key Inn with a 'VACANCY' sign below it.

3. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

ben

₹24,856

₹27,963 total

includes taxes & fees

14 Oct - 15 Oct

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

A spacious room with a large bed, a sofa, a chair, a small table, and a television.

A pathway flanked by lush green foliage leading to a gated entrance.

A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.

4. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.4 km from Jackson Square

William

₹23,120

₹26,010 total

includes taxes & fees

25 Oct - 26 Oct

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

A colonial-style building with a porch, surrounded by lush tropical vegetation.

A bar area with a counter, chairs, and a clock.

A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.

5. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Gisele

₹32,219

₹36,246 total

includes taxes & fees

14 Oct - 15 Oct

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

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

A living room with a sofa, a glass coffee table, a TV, and a painting on the wall.

A spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.

6. The Conch House Heritage Inn

Old Town Key West, 0.7 km from Jackson Square

John

₹27,355

₹30,775 total

includes taxes & fees

28 Oct - 29 Oct

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.

A spacious living room with a sofa, chairs, and a dining table. There are large windows with blinds, a door leading to a patio, and a ceiling with exposed beams.

A narrow room with a bed, a potted plant, and a window with blinds.

7. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.1 km from Jackson Square

Nestor

₹21,678

₹28,384 total

includes taxes & fees

15 Oct - 16 Oct

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

A house with a porch, a table, and a door with a number '6'.

A covered porch with wicker furniture, a large potted plant, and a sign for Villas Key West.

A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.

8. Key West Villas

Downtown Key West, 0.3 km from Jackson Square

Margaret

₹24,913

₹28,028 total

includes taxes & fees

15 Oct - 16 Oct

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

A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.

A covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.

A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

9. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

₹34,386

₹44,072 total

includes taxes & fees

15 Oct - 16 Oct

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

A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

A lush garden with a variety of tropical plants and a paved walkway.

A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

10. Duval House

Downtown Key West, 0.4 km from Jackson Square

Cliff

₹17,155

₹21,358 total

includes taxes & fees

27 Oct - 28 Oct

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

A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.

A row of blue bicycles parked under a tree, with a white fence and a building in the background.

A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.

11. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Justyn

₹11,435

₹15,259 total

includes taxes & fees

14 Oct - 15 Oct

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

A covered walkway with a wooden ceiling, white railings, and a brick path.

A pool area with lounge chairs and a wooden building with balconies.

A garden with a pond, rocks, and various plants.

12. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Osvaldo

₹17,792

₹20,015 total

includes taxes & fees

14 Oct - 15 Oct

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

A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.

A cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.

A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

13. The Mermaid & Alligator

Old Town Key West, 0.8 km from Jackson Square

Adam

₹22,331

₹25,123 total

includes taxes & fees

14 Oct - 15 Oct

A pool area with lounge chairs and palm trees.

A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.

A sign for Santa Maria Resort surrounded by lush greenery and palm trees.

A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

14. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

₹28,924

₹39,069 total

includes taxes & fees

14 Oct - 15 Oct

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

A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

A grand staircase with ornate railings and a chandelier.

A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

15. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

Amy

₹13,343

₹27,133 total

includes taxes & fees

28 Oct - 29 Oct

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

A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.

A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.

A two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.

16. Westwinds Inn

Historic Seaport, 0.8 km from Jackson Square

Anthony

₹15,517

₹17,456 total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel with a pool, bicycles, and lush greenery.

The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

A two-story yellow house with a porch, white railings, and green shutters.

17. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

sam

₹8,619

₹16,227 total

includes taxes & fees

25 Oct - 26 Oct

A green house with a white porch, a flag, and a sign advertising a property for sale.

A room with a ceiling fan, an air conditioning unit, a window with blinds, a sofa with patterned cushions, a small round table, and a floor lamp.

A bathroom with a vanity, a mirror, and a window with blinds.

A covered porch with wicker furniture, potted plants, and a view of the house.

18. L'Habitation Guest House - Adults Only

Historic Seaport, 0.2 km from Jackson Square

Richard

₹16,293

₹18,330 total

includes taxes & fees

28 Oct - 29 Oct

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

A covered outdoor dining area with white chairs and tables, surrounded by lush greenery and a wooden deck.

A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

A hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.

19. Coco Plum Inn

Downtown Key West, 0.1 km from Jackson Square

Riley

₹17,198

₹19,347 total

includes taxes & fees

14 Oct - 15 Oct

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

A wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.

A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.

A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.

20. Ella's Cottages - Key West Historic Inns

Old Town Key West, 0.5 km from Jackson Square

Henry

₹21,072

₹28,556 total

includes taxes & fees

14 Oct - 15 Oct

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Compare popular hotels close to Jackson Square

Property	Property class	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,004 reviews	View
Douglas House - Adults Only	9.8 Exceptional 555 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,002 reviews	View
Simonton Court Historic Inn & Cottages	9.8 Exceptional 1,005 reviews	View
The Gardens Hotel	9.8 Exceptional 1,008 reviews	View

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"The breakfast should be a little bit less greasy"

The Cabana Inn Key West - Adults Only

10/10 Excellent

"Everything was perfect. Nice breakfast, immaculate pool. Very clean room and property grounds. On issue was that the hot tub was like warm -not hot."

Amsterdam's Curry Mansion Inn

8/10 Good

"Great location. Large rooms. Pool area is nice. Only gripes are the limited parking, and the fact that you can’t ever check in before 4pm, even though you can see the room sitting there empty. Also, the 10am checkout in an area known for nightlife is downright criminal."

Coco Plum Inn

10/10 Excellent

"This B&B was very convenient to Duval Street. The pool area was wonderful with places to sit and get together with our friends. We found the bed and pillows to be very comfortable and the manager was phenomenal! We had to check out at 11:00 but needed a place to hang out until 4:00 to catch the ferry. We were allowed to store our luggage and make use of the pool. We would definitely stay at Coco Plum again if we ever go back to Key West."

Winslow's Bungalows - Key West Historic Inns

8/10 Good

"Le déjeuner, le service de bar et l’accueil était top. L’attitude des femmes de ménage et la propreté des entretiens dans la chambre étaient très ordinaire."

Pegasus International Hotel

8/10 Good

"The room was good. The cleaning staff was not aligned. Some did more than others. The pool and the hot tub were excellent. The breakfast was continental breakfast. Coffee, orange juice, pastries. Very secure needed code access to get back into the hotel after hours."

The Marquesa Hotel

10/10 Excellent

"The staff was friendly and my room was clean , and the hotel was very nice!"

Paradise Inn Key West - Adults Only

10/10 Excellent

"Would definitely stay here again. Nothing but good things to say about paradise inn. The staff goes above and beyond and helped make the stay as easy and enjoyable as possible."

Opal Key Resort & Marina, Key West

10/10 Excellent

"Great location. Walking distance to Anything you’d want to do in Key West. Housekeeping staff very attentive. Valets very friendly and quick to attend. Room was clean spacious and bed comfortable. Restaurant was just OK. Staff there not as friendly and attentive. Pool was ok."

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.

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A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 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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We Cycle Key West

You can do some window-shopping at We Cycle Key West during your stay in Key West.

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St. Paul's Episcopal Church

9.0/10 (73 reviews)

St. Paul's Episcopal Church is just one of the places to see in Key West, so why not enjoy the other things to explore during your travels? Discover the area's lively bars and its lively festivals.

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Key West Film Society

7.6/10 (9 reviews)

You can get tickets for a performance at Key West Film Society during your trip to Key West. In the area, take in the lively festivals and beautiful sunsets.

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The Key West Theater

You can make plans for a show at The Key West Theater on your trip to Key West. Discover the area's great live music or seek out its cycling trails.

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Red Barn Theater

8.0/10 (10 reviews)

You can get tickets for a performance at Red Barn Theater on your trip to Key West. Wander the seaside and beautiful beaches in the area.

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Hellings House Museum

You can spend an afternoon exploring the galleries in Hellings House Museum during your travels in Key West. Experience the area's entertainment choices and great live music.

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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 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

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

2. Douglas House - Adults Only

3. Orchid Key Inn - Adults Only

4. Simonton Court Historic Inn & Cottages

5. The Gardens Hotel

6. The Conch House Heritage Inn

7. Alexander's Guesthouse - Adult Exclusive

8. Key West Villas

9. The Marquesa Hotel

10. Duval House

11. The Grand Guesthouse

12. Island City House Hotel

13. The Mermaid & Alligator

14. Santa Maria Suites

15. Southernmost House - Adult Exclusive

16. Westwinds Inn

17. Silver Palms Inn & Historic Homes

18. L'Habitation Guest House - Adults Only

19. Coco Plum Inn

20. Ella's Cottages - Key West Historic Inns

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

The Cabana Inn Key West - Adults Only

Amsterdam's Curry Mansion Inn

Coco Plum Inn

Winslow's Bungalows - Key West Historic Inns

Pegasus International Hotel

The Marquesa Hotel

Paradise Inn Key West - Adults Only

Opal Key Resort & Marina, Key West

Other attractions near Jackson Square

San Carlos Institute - Casa Cuba

Duval Street

We Cycle Key West

St. Paul's Episcopal Church

Key West Film Society

The Key West Theater

Red Barn Theater

Hellings House Museum

Frequently asked questions