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

Find hotels near Jackson Square, Key West from $120

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Filter by

Star rating

Guest rating

Our top choices for Jackson Square hotels

A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.
A beachside lounge with chairs and umbrellas, overlooking the ocean.
A beachfront resort with a prominent sign, white balconies, and tropical landscaping.

1. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Uptown - Upper Duval, 0.6 mi from Jackson Square
United States
Deaenna
$210 nightly
$237 total
Sep 8 - Sep 9
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
A multi-story hotel with a pink facade, multiple balconies, and a prominent 'LA CONCHA' sign.
A spacious lobby with a checkered floor, a central seating area with wicker chairs, a large potted plant, and a staircase with a metal railing.
A beach with clear turquoise water, snorkelers, and a large building in the background.
A modern hotel entrance with a black and white striped curtain, wicker furniture, potted plants, and a sign for the Autograph Collection.

2. La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
Historic Seaport, 0.1 mi from Jackson Square
United States
Fatima
$219 nightly
$246 total
Sep 1 - Sep 2
Total with taxes and fees
La Concha Key West, Autograph Collection
A wooden deck with wicker furniture, a white staircase, and a lush garden area.
A hotel room with a large bed, a view of a swimming pool, and a balcony with outdoor seating.
A two-story house with a balcony, surrounded by palm trees and a clear blue sky.
A hotel entrance with a sign reading "Heron House Office."

3. Heron House - Adult Only

Heron House - Adult Only
Downtown Key West, 0.2 mi from Jackson Square
United States
Natalia
$136 nightly
$154 total
Sep 1 - Sep 2
Total with taxes and fees
Heron House - Adult Only
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A balcony with a view of the ocean, a sofa, and a massage table.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.

4. Pier House Resort & Spa

Pier House Resort & Spa
Historic Seaport, 0.4 mi from Jackson Square
United States
Mark
$310 nightly
$349 total
Sep 9 - Sep 10
Total with taxes and fees
Pier House Resort & Spa
A two-story house with a covered porch, a brick pathway, and a large tree.
A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.
A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.
A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

5. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.2 mi from Jackson Square
United States
Darrell
$276 nightly
$310 total
Sep 15 - Sep 16
Total with taxes and fees
The Marquesa Hotel
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A couple walking along a poolside pathway surrounded by lush greenery.
A colonial-style building with a porch, surrounded by lush tropical vegetation.
A bar area with a counter, chairs, and a clock.

6. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.2 mi from Jackson Square
United States
Brian
$224 nightly
$252 total
Sep 7 - Sep 8
Total with taxes and fees
The Gardens Hotel
A hotel with a swimming pool, balconies, and a view of the sea.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.
A beach wedding setup with white chairs, a wooden arch, and lanterns.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

7. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Historic Seaport, 0.5 mi from Jackson Square
United States
FRANK
$263 nightly
$296 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Centric Key West Resort and Spa
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.
A spacious lobby with green sofas, a coffee table, and a dining area.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

8. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Casa Marina, 1 mi from Jackson Square
United States
Dirk
$271 nightly
$305 total
Sep 13 - Sep 14
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
A hotel with a covered entrance, multiple balconies, and palm trees.
A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.
A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.
A waterfront hotel with multiple balconies, a dock, and boats.

9. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West, 0.3 mi from Jackson Square
United States
Melissa
$294 nightly
$331 total
Sep 1 - Sep 2
Total with taxes and fees
Opal Key Resort & Marina, Key West
A two-story building with a covered entrance, palm trees, and a bench outside.
A white picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery.
A bright room with a staircase, two windows overlooking a pool area, and two wicker chairs with cushions.
A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights.

10. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
Old Town Key West, 0.5 mi from Jackson Square
United States
Stacey
$260 nightly
$293 total
Sep 1 - Sep 2
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns
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 entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.
A covered porch with wicker furniture, a large potted plant, and a sign for Villas Key West.

11. Key West Villas

Key West Villas
Downtown Key West, 0.2 mi from Jackson Square
United States
Margaret
$229 nightly
$258 total
Sep 3 - Sep 4
Total with taxes and fees
Key West Villas
A bright green porch with hanging planters, a wooden chair, and a railing.
A marina with multiple boats docked, wooden pilings, and a dock with ropes.
A bar area with a wooden counter, colorful decorations, and a sign with motivational ocean-themed text.

12. Caribbean House

Caribbean House
Bahama Village, 0.2 mi from Jackson Square
United States
David
$165 nightly
$183 total
Sep 1 - Sep 2
Total with taxes and fees
Caribbean House
A narrow pathway flanked by white buildings with balconies, leading to a gated entrance.
A covered outdoor dining area with tables and chairs, surrounded by lush greenery and a view of a building.
A hotel with a signboard, palm trees, and a red carpet leading to the entrance.
A modern hotel room with a large bed, a flat-screen TV, a vanity with a mirror, and a view of the outdoor pool area.

13. The Saint Hotel Key West, Autograph Collection, Adult Only

The Saint Hotel Key West, Autograph Collection, Adult Only
Historic Seaport, 0.1 mi from Jackson Square
United States
R Frederick
$169 nightly
$190 total
Sep 7 - Sep 8
Total with taxes and fees
The Saint Hotel Key West, Autograph Collection, Adult Only
A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.
A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.
A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.
A pool with a lion head sculpture in the center.

14. Artist House Key West

Artist House Key West
Historic Seaport, 0.2 mi from Jackson Square
United States
Gary
$142 nightly
$159 total
Sep 7 - Sep 8
Total with taxes and fees
Artist House Key West
A modern interior with a staircase, a sofa set, a wooden table, and a television.
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.
A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.
A spacious room with a large bed, a sofa, a chair, a small table, and a television.

15. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.2 mi from Jackson Square
United States
Robin
$129 nightly
$145 total
Sep 1 - Sep 2
Total with taxes and fees
Simonton Court Historic Inn & Cottages
A covered porch with white railings, wooden benches, and a hanging light fixture.
A pool area with lounge chairs and a small palm tree.
A bedroom with a four-poster bed, a wicker chair, a wooden dresser, and a television.
A living room with a large mirror, a wicker chair, a television on a wooden cabinet, and a window with a view of palm trees.

16. Marrero's Guest Mansion

Marrero's Guest Mansion
Downtown Key West, < 0.1 mi from Jackson Square
United States
Michael
$219 nightly
$246 total
Sep 1 - Sep 2
Total with taxes and fees
Marrero's Guest Mansion
A swimming pool with clear water, surrounded by lush greenery and palm trees.
A bedroom with a bed, a ceiling fan, an air conditioning unit, a bedside table, a lamp, and a window with blinds.
A bathroom with a white sink, three bottles of body lotion, and a white towel.
A yellow building with a blue door and shutters, a number '302' on the wall, and a small porch area.

17. Tranquility Guest House

Tranquility Guest House
Bahama Village, 0.2 mi from Jackson Square
United States
Steven
$164 nightly
$184 total
Sep 22 - Sep 23
Total with taxes and fees
Tranquility Guest House
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A tropical setting with palm trees and a building with a white facade and dark roof.
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.
A covered outdoor area with a pool, palm trees, and lounge chairs.

18. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Historic Seaport, 0.4 mi from Jackson Square
United States
Danny Lee
$238 nightly
$267 total
Sep 13 - Sep 14
Total with taxes and fees
The Marker Key West Harbor Resort
A beach with a wooden pier, palm trees, and beach umbrellas.
A modern bar area with a central island, white bar stools, and a view of the ocean.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

19. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Uptown - Upper Duval, 0.8 mi from Jackson Square
United States
Joseph
$238 nightly
$267 total
Sep 8 - Sep 9
Total with taxes and fees
The Reach Key West, Curio Collection by Hilton
A pool area with lounge chairs and a cabana.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
A balcony with a table set for breakfast, overlooking the sea.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

20. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Historic Seaport, 0.5 mi from Jackson Square
United States
Brian
$328 nightly
$369 total
Sep 1 - Sep 2
Total with taxes and fees
Ocean Key Resort - A Noble House Resort
View all properties

Compare popular hotels close to Jackson Square

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only
10.0
Exceptional
1,005 reviews
View
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
9.8
Exceptional
163 reviews
View
A modern interior with a staircase, a sofa set, a wooden table, and a television.
Simonton Court Historic Inn & Cottages
9.8
Exceptional
1,001 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,002 reviews
View
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
9.8
Exceptional
1,003 reviews
View

Top Jackson Square Hotel Reviews

Heron House - Adult Only

Heron House - Adult Only

8/10 Good
"great location friendly staff. they do have poolside construction going on currently."
colleen 1-night trip
Posted 9 hours ago
Heron House - Adult Only
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

10/10 Excellent
"Great boutique hotel! The room was clean, the bed was very comfortable, and the location was perfect—just one block from Duval Street, with restaurants nearby. Breakfast was also better than I expected! Live music by the pool (afternoon and during breakfast) and at night was very quiet! Overall, a very pleasant stay!"
gabriela 3-night trip
Posted 9 hours ago
Lighthouse Hotel - Key West Historic Inns
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Best Hotel in the Key West. Room was very clean, best staff services. Beautiful beach view and breakfast was delicious. My husband and I love this place. 💯 recommend."
Vivian 1-night trip
Posted 10 hours ago
Pier House Resort & Spa
Duval Inn

Duval Inn

10/10 Excellent
"Honestly, great location and loved our room! The only thing is I don’t think we got our VIP welcome gift. Not the end of the world!"
Courtney 2-night trip
Posted 12 hours ago
Duval Inn
Duval House

Duval House

10/10 Excellent
"What an amazing experience. The Duval house is the perfect quiet respite from the wacky fun times of Key West!"
Lori 2-night trip
Posted 13 hours ago
Duval House
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"Loved the location overall 100%"
Janet 3-night trip
Posted 1 day ago
Hyatt Centric Key West Resort and Spa
Coco Plum Inn

Coco Plum Inn

10/10 Excellent
"The pool is so topically beautiful and clean!! Room was cool and comfortable!! Will definitely be back!"
Shaun 5-night trip
Posted 4 days ago
Coco Plum Inn
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"Its was very clean. The staff was great."
Scott 2-night trip
Posted 4 days ago
The Cabana Inn Key West - Adults Only
Tranquility Guest House

Tranquility Guest House

8/10 Good
"Nice place. Very quiet and peaceful. Some minor amenities would be helpful (coffee pot in the room, ice machine)."
Richard 3-night trip
Posted 7 days ago
Tranquility Guest House

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
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.
See properties

We Cycle Key West

You can search for that perfect souvenir at We Cycle Key West during your trip to Key West.
See properties

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.
See properties

Key West Film Society

7.6/10 (9 reviews)
You can get tickets for a performance at Key West Film Society during your stay in Key West. In the area, take in the lively festivals and beautiful sunsets.
See properties

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 biking trails.
See properties

Red Barn Theater

8.0/10 (10 reviews)
You can enjoy a show at Red Barn Theater on your trip to Key West. Wander the seaside and beautiful beaches in the area.
See properties

Hellings House Museum

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

Find out more about Jackson Square

Top reasons to visit Jackson Square

  • Breathtaking Sunsets: Experience stunning sunsets that paint the sky over Jackson Square, making it a perfect spot for evening relaxation.
  • Rich History: Explore the historic houses and learn about the vibrant past of Key West through guided tours.
  • Vibrant Festivals: Enjoy lively festivals that showcase local culture, music, and arts throughout the year.
  • Charming Streets: Wander through quaint streets filled with unique shops and local eateries, enhancing your visit.
  • Family-Friendly Activities: Engage in a variety of activities suitable for all ages, ensuring fun for the whole family.

Find great hotels near Jackson Square

Discover the charm of Jackson Square with a variety of lodging options, including resorts and cozy bed & breakfasts. Perfect for those seeking adventure or a romantic getaway, these accommodations offer essential amenities such as convenient parking facilities and easy access to local attractions. Experience a memorable stay in this historic area, where you can explore the vibrant culture and enjoy the beautiful surroundings of Key West.

  • La Concha Key West, Autograph Collection: A 4-star hotel with a guest rating of 8.8, La Concha Key West, Autograph Collection is located a mere 0.1 mile from Jackson Square. This charming property offers a beach-themed escape for families and adventure seekers alike. Guests can enjoy direct beach access and engage in a variety of adventure sports, including parasailing and windsurfing, either on-site or nearby. Family-friendly amenities such as cribs and window guards ensure a safe and enjoyable stay for travelers with children. Experience the vibrant atmosphere and rich history of Key West from this luxurious base.
  • Opal Key Resort & Marina, Key West: Rated 9.2 out of 10, Opal Key Resort & Marina is a 4-star accommodation located 0.3 miles from Jackson Square. Ideal for adventure enthusiasts and pet lovers, this resort offers a plethora of exciting activities, including snorkeling and boat tours. The property is pet-friendly, allowing dogs with certain policies in place. Guests can explore the beautiful waters of Key West or relax in the luxurious amenities provided, ensuring a memorable vacation experience for both you and your furry friends.
  • Heron House - Adult Only: With a guest rating of 9.0, Heron House - Adult Only is a 3.5-star bed and breakfast situated 0.2 miles from Jackson Square. This adults-only retreat is perfect for couples and solo travelers seeking a serene getaway. The property offers a variety of adventure sports nearby, including snorkeling and kayaking. Guests will appreciate the intimate atmosphere and personalized service, making it an ideal location for those looking to unwind and explore the beauty of Key West.

Where to stay near Jackson Square

Discover the vibrant charm of Jackson Square in Key West, where you can immerse yourself in the tropical ambiance and rich history. Explore the quaint streets of Historic Key West, visit vacation homes near Jackson Square, and enjoy the lively atmosphere around Thomas Street. With numerous spots for visitors to relax and adventure, your stay promises a unique blend of excursions and local culture that will make your vacation unforgettable.

  • Key West: Nestled at the southernmost tip of the continental U.S., Key West is a vibrant city known for its laid-back atmosphere and stunning sunsets. Situated on a beautiful island, it offers a unique blend of tropical charm and urban energy. Visitors flock here for family-friendly activities, cultural experiences, and business events. Popular attractions include local shopping areas, beaches, and bustling resorts. Peak travel times occur in January, March, and September, ensuring that you can mingle with fellow travelers while enjoying the scenic beachside streets and lively pier.
  • Old Town Key West: Old Town Key West, where Jackson Square is located, is a historic neighborhood that exudes a unique blend of charm and excitement. Known for its colorful architecture and vibrant nightlife, this area is a must-visit for families and business travelers alike. The streets are lined with shopping venues and cozy resort options, making it perfect for leisurely strolls and sunset watching. Peak travel months in March, July, and December highlight the area's popularity, so be prepared to soak in the lively atmosphere while exploring its beautiful beaches and family-friendly activities.
  • Key West Historic District: Just a short 0.3 miles from Jackson Square, the Key West Historic District is a treasure trove of architectural wonders and rich history. This neighborhood is popular among families and business travelers, offering a myriad of shopping options, resorts, and charming streets to wander. The area's appeal peaks during March, July, and December, providing visitors with a lively yet relaxed atmosphere. Enjoy the local landmarks, family beaches, and cultural experiences that make this district a delightful addition to your Key West adventure.

Things to do in Jackson Square

Jackson Square in Key West offers a variety of activities for visitors, including breathtaking sunsets, lively festivals, and biking adventures. You can explore the square through guided tours that highlight its rich history, or enjoy a day trip or weekend getaway to soak in the vibrant atmosphere and local culture. Don't miss the chance to experience the charm of Jackson Square while enjoying its numerous attractions.

Shopping

In Jackson Square, explore local shops like the Key West Butterfly and Nature Conservatory for unique souvenirs. If you're up for a drive, visit the nearby Mallory Square for more shopping options and enjoy the vibrant atmosphere of local artisans and craftspeople.

Recreation

In Key West, indulge in rejuvenating experiences at the Zen Spa, offering holistic treatments and serene surroundings. Enjoy yoga sessions at the nearby beach, where the sound of waves enhances relaxation, or take a leisurely stroll through the lush gardens at the Key West Butterfly and Nature Conservatory.

Adventure

Explore the vibrant art scene at Jackson Square, where you can enjoy street performances and local artists showcasing their work. Experience the lively atmosphere while sampling delicious food from nearby cafés. Don't miss the opportunity to capture stunning photos of the historic architecture surrounding the square.

Nightlife

In Key West, Jackson Square buzzes with vibrant nightlife, featuring lively bars like The Green Parrot and Sloppy Joe's, where you can enjoy live music and dance. The atmosphere is laid-back yet festive, perfect for mingling and soaking up the unique island vibe.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Jackson Square

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Jackson Square are August to October, where the prices are slightly lower. This is in comparison to February to April, where prices are slightly higher.
  • The best time to book a hotel: Booking a hotel around Jackson Square about 1 month out from when you are planning to stay is usually when prices are lowest. If you're a little more spontaneous, you could also peruse Expedia's last minute deals for hotels, look out for the green banner below the price, as this indicates a cheaper deal.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Jackson Square is Tuesday. The most expensive day to stay around Jackson Square is Friday.
  • Find cheap hotels on Expedia: Expedia’s search tool makes it easy for you to choose your budget, desired location, and other preferences. You can arrange your results to display prices from lowest to highest, ensuring you find the most affordable hotels first. Additionally, you can refine your search by hotel type; for instance, selecting the Eco-certified filter will show you a list of sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay at Jackson Square with your flights and activities through an Expedia package deal.

Find the best attractions near Jackson Square

Jackson Square in Key West offers a vibrant mix of historic houses, charming streets, and a lively modern square. Visitors can immerse themselves in the local culture while enjoying family-friendly activities and the unique city atmosphere. From exploring nearby attractions to experiencing the rich history of the area, there’s something for everyone to enjoy in this picturesque destination.

  • Duval Street: A vibrant hub of activity, Duval Street is renowned for its lively atmosphere, featuring an array of bars, shops, and restaurants. Just 0.1 mile from Jackson Square, it's perfect for strolling, people-watching, and enjoying the local nightlife.
  • Mallory Square: Located 0.4 mile away, Mallory Square is the heart of Key West's sunset celebrations. This modern square offers stunning views of the Gulf of Mexico, street performers, and local artisans, making it an ideal spot to soak in the local culture.
  • Ernest Hemingway Home and Museum: A short 0.3 mile stroll leads you to this historic house, where the famed author lived and wrote. The museum showcases Hemingway's life, work, and the beautiful gardens, providing a unique glimpse into his legacy.

Best time to go to Jackson Square

The best time to visit Jackson Square can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Jackson Square falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature around Jackson Square falls in January, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January71.1°F (21.7°C)No RainMostly SunnyAverageAverage
February72.1°F (22.3°C)No RainMostly SunnyAverageSlightly High
March73.4°F (23.0°C)No RainMostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No RainMostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnySlightly LowAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Light RainMostly SunnySlightly HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnySlightly LowSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowSlightly Low
November76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
December73.9°F (23.3°C)No RainMostly SunnySlightly HighAverage

The nearest major airports for your trip to Jackson Square

Traveling to Jackson Square in Key West, Florida is convenient with access to nearby airports. Key West International Airport (EYW) is situated 3 miles from Jackson Square, offering excellent hotel options such as the 5-star Casa Marina Key West, 2 miles away, and the 4-star DoubleTree Resort by Hilton Grand Key, just 0.6 miles from the airport. Marathon Airport (MTH) is another option, located 49 miles from Jackson Square, with hotels like the 4.5-star Isla Bella Beach Resort & Spa, 4 miles away, and the 4-star Tranquility Bay Beachfront Hotel, 3 miles from the airport. Both airports provide convenient transportation services to their respective hotels.

Frequently asked questions

What are the top-rated hotels near Jackson Square?
Discovering the top-rated hotels near Jackson Square in Key West is an exciting journey toward finding your perfect getaway.Almond Tree Inn Hotel - Adults OnlyAlmond Tree Inn Hotel is an inviting adults-only retreat located just a 10-minute walk from Jackson Square. With an impressive review rating of 10, this 3.5-star hotel ensures a memorable stay with amenities like an outdoor pool, hot tub, and a beautiful terrace to relax. Guests appreciate the complimentary breakfast, designer toiletries, and the option for nearby windsurfing and snorkeling. The hotel also features electric car charging stations and is designed with an elegant Art Deco hotel style, making it a unique choice for travelers.The Gardens HotelThe Gardens Hotel, only a 5-minute stroll from Jackson Square, boasts a remarkable review rating of 9.8 and a 4.0-star rating. This hotel offers a lush garden setting and a charming outdoor pool, perfect for unwinding after a day of exploring. Guests can enjoy complimentary cooked breakfasts and relax in spacious rooms featuring Egyptian cotton sheets. Unique amenities like in-room private pools and a yoga class on-site ensure travelers have a tranquil and rejuvenating experience.Orchid Key Inn - Adults OnlyOrchid Key Inn is a delightful adults-only hotel, situated just 9 minutes from Jackson Square, rated an impressive 9.8 by travelers. This 3.5-star hotel offers a blend of comfort and style, featuring an outdoor pool with sun loungers and a private hot tub for a more intimate experience. Guests enjoy complimentary breakfasts and have access to nearby kayaking and snorkeling adventures. The presence of designer toiletries and a concierge service adds to the overall appeal, making it a lovely choice for visitors to Key West.
What hotels are within walking distance to Jackson Square?
Discover a selection of top-rated hotels just a short stroll from Jackson Square, perfect for your Key West getaway.Almond Tree Inn Hotel - Adults OnlyAlmond Tree Inn Hotel is an inviting 3.5-star accommodation located just a 10-minute walk from Jackson Square. Rated 10 by travelers, this adults-only retreat features an outdoor pool surrounded by sun loungers, perfect for a leisurely day in the sun. Guests can enjoy complimentary daily breakfast and relax in the hot tub after a day of exploring. With amenities like Egyptian cotton sheets and a terrace, it offers a cozy ambiance for a memorable stay.The Gardens HotelThe Gardens Hotel, a charming 4-star hotel, is located only 5 minutes on foot from Jackson Square, with a stellar review rating of 9.8. This boutique hotel features a beautiful outdoor pool and a garden view restaurant, perfect for dining al fresco. Guests can indulge in complimentary cooked breakfast and unwind with yoga classes on-site. The hotel's unique layout and lush landscaping provide a tranquil oasis amidst the vibrant Key West atmosphere.Orchid Key Inn - Adults OnlyOrchid Key Inn, rated 9.8 by travelers, offers a delightful stay just 9 minutes from Jackson Square. This 3.5-star adults-only hotel features an outdoor pool and a relaxing hot tub, creating an ideal environment for unwinding. Guests can enjoy free breakfast daily and take advantage of the nearby beach activities, including snorkeling and kayaking. With its art deco design and premium bedding, it provides a chic and comfortable retreat.
How much is a hotel near Jackson Square?
Staying near Jackson Square is a treat, with plenty of hotels from $120 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a vacation during weekends or around public holidays.
What are the most popular family-friendly hotels near Jackson Square?
For families looking for top-rated hotels near Jackson Square, Key West offers some fantastic options that cater to both comfort and fun.Margaritaville Beach House Key WestMargaritaville Beach House Key West, a 4-star hotel just 2.9 miles from Jackson Square, welcomes families with open arms. Rated 8.8 by travelers, this hotel offers a range of family-friendly amenities including a pool accessible to all, a kitchenette for in-room meals, and toys to keep children entertained. Guests can also enjoy the nearby beach, outdoor activities like kayaking and snorkeling, and the comfort of daily housekeeping.Blue Flamingo Resort Key WestBlue Flamingo Resort Key West is a charming 4-star hotel located 3.7 miles from Jackson Square, a review rating of 7.8 by travelers. This family-friendly resort features connecting rooms and an arcade game room, providing endless entertainment for kids. Guests can also relax by the outdoor pool, enjoy snacks from the poolside bar, and take advantage of the onsite picnic area.Hyatt Centric Key West Resort and SpaHyatt Centric Key West Resort and Spa is a luxurious 4-star option just a 12-minute walk from Jackson Square, with an impressive travelers' rating of 9.0. This family-friendly resort offers amenities such as a pool with accessible features and kids' meals at the onsite restaurant. Guests can unwind with spa services, enjoy beach access, and enjoy various water sports, making it a perfect getaway for families.
Which hotels near Jackson Square offer the best views?
Explore the best hotels near Jackson Square that not only offer comfort but also stunning views for your Key West adventure.The Gardens HotelThe Gardens Hotel is a top-rated 4-star hotel with a remarkable review rating of 9.8, located just a 5-minute walk from Jackson Square. This charming hotel features a beautiful garden view and offers a complimentary breakfast, an outdoor pool, and unique amenities like in-room massages. Guests appreciate the tranquil atmosphere and close nearby the vibrant sights of Key West, making it an ideal retreat.Hyatt Centric Key West Resort and SpaHyatt Centric Key West Resort and Spa, rated 9.0 by travelers, is a 4-star gem located just a 12-minute walk from Jackson Square. Guests can indulge in ocean views from their furnished balconies while enjoying amenities like a full-service spa and an outdoor pool. The beach is nearby, and there's a restaurant offering ocean views, making it a perfect choice for those seeking relaxation and picturesque scenery.Casa Marina Key West, Curio Collection by HiltonCasa Marina Key West, Curio Collection by Hilton boasts an impressive review rating of 8.4 and is situated 1.3 miles from Jackson Square. This 4-star resort features an ocean view and offers a stunning beachfront location. Guests can enjoy a full-service spa, outdoor pool, and a variety of water sports such as sailing and kayaking, ensuring a delightful stay with breathtaking views at every turn.
What are the best affordable hotels near Jackson Square?
Finding the best affordable hotels near Jackson Square offers travelers a wonderful opportunity to explore this vibrant area without breaking the bank.The Grand GuesthouseThe Grand Guesthouse is situated 1.2 miles from Jackson Square and offers a cozy escape with a great traveler rating score of 9.6. This hotel features free continental breakfast and WiFi, along with free parking, making it a practical choice for travelers. Enjoy the terrace, garden, and convenient access to nearby historical sites and beautiful beaches, perfect for a relaxing getaway.Simonton Court Historic Inn & CottagesSimonton Court Historic Inn & Cottages is a charming option just a 7-minute walk from Jackson Square. Rated by travelers with an impressive 9.8, this inn offers free continental breakfast and WiFi, making it a great choice for budget-conscious travelers. Guests can also enjoy the outdoor pool, terrace, and nearby marina for kayaking and boat tours, ensuring a delightful stay in Key West.LA TE DA Hotel - Adults OnlyLA TE DA Hotel - Adults Only, located 12 minutes on foot from Jackson Square, boasts a stellar review rating of 9.8. This adults-only venue provides free WiFi and toiletries for a straightforward experience. Guests can unwind by the outdoor pool or take advantage of the nearby beach and marina for snorkeling and sailing adventures, making it an ideal retreat for couples.
What are the best boutique hotels near Jackson Square?
Discover the charm of boutique hotels near Jackson Square, perfect for travelers seeking a top-rated stay in Key West.Artist House Key WestArtist House Key West, a 3.5-star boutique hotel, offers an exceptional experience just a 5-minute walk from Jackson Square, with an impressive review rating of 9.8 by travelers. Guests can indulge in complimentary daily breakfast and enjoy amenities such as a hot tub and concierge service. The hotel also provides easy access to nearby beach activities including snorkeling and kayaking, ensuring a delightful stay in this vibrant location.Weatherstation InnWeatherstation Inn is another fantastic boutique option, located only 5 minutes from Jackson Square and rated 9.4 by travelers. This charming inn features an outdoor pool and a terrace, providing perfect spots to relax. Guests can enjoy a complimentary continental breakfast and enjoy nearby water activities like snorkeling and sailing. The inn's adults-only policy offers a serene escape for couples looking to unwind.The Inn on FlemingThe Inn on Fleming, a 3.5-star boutique hotel, is situated 12 minutes from Jackson Square and boasts a review rating of 9.4 from travelers. This inviting inn features a refreshing outdoor pool and complimentary breakfast, making it an ideal choice for a relaxing stay. Guests can easily explore nearby attractions and enjoy activities such as windsurfing and boat tours, all while basking in the unique charm of Key West.
Are there any hotels with pools close to Jackson Square?
For travelers seeking a refreshing stay near Jackson Square, these hotels with pools offer the perfect blend of comfort and convenience.Blue Flamingo Resort Key WestBlue Flamingo Resort Key West is situated 3.7 miles from Jackson Square and offers a delightful outdoor pool experience with sun loungers and cabanas for relaxation. Rated 7.8 by travelers, this 4-star hotel also features a poolside bar, fitness facilities nearby, and a complimentary shuttle service for local attractions. Guests can enjoy spacious rooms equipped with kitchenettes, ensuring a comfy stay.Pier House Resort & SpaLocated a mere 10-minute stroll from Jackson Square, Pier House Resort & Spa is a luxurious 4-star resort with a captivating outdoor pool featuring sun loungers and poolside service. Rated 9.0 by travelers, it offers an array of amenities including a full-service spa, beachfront dining, and complimentary beach towels. Guests can unwind in elegantly furnished rooms and enjoy a range of wellness treatments for a truly relaxing getaway.Southernmost Beach Resort and GuesthousesJust a short 15-minute walk from Jackson Square, Southernmost Beach Resort and Guesthouses is a 4-star gem that boasts a beautiful outdoor pool with cabanas and a poolside bar. With an impressive review rating of 8.6, this resort offers travelers beach access, a full-service spa, and on-site dining options with ocean views. Families will appreciate the free cribs and kid-friendly amenities available.
What are the best pet-friendly hotels near Jackson Square?
Discover the best pet-friendly hotels near Jackson Square, offering top-rated stays where you and your furry friends can enjoy the vibrant atmosphere of Key West.The Gardens HotelThe Gardens Hotel is a charming 4-star retreat just a 5-minute walk from Jackson Square, an impressive 9.8 travelers' rating. This pet-friendly haven welcomes your dogs and provides essential amenities like food and water bowls. Guests can also indulge in a relaxing outdoor pool, free breakfast, and serene garden views, ensuring a delightful stay in a picturesque setting.Artist House Key WestArtist House Key West, rated 9.8 by travelers, is a delightful 3.5-star hotel located only 5 minutes from Jackson Square. This inviting hotel welcomes pets and offers amenities such as food and water bowls for your furry companions. Guests can enjoy a complimentary buffet breakfast, relax in the hot tub, and explore nearby kayaking and snorkeling activities, making it a perfect choice for a memorable getaway.The Garden HouseThe Garden House, a cozy 3-star hotel situated 8 minutes from Jackson Square, has a great traveler rating score of 9.2. This pet-friendly accommodation allows dogs and provides food and water bowls for your pets. Guests can unwind by the outdoor pool, enjoy free breakfast, and explore the nearby historical district, making it an ideal base for discovering the beauty of Key West.
Can I book a fully refundable hotel close to Jackson Square?
Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Jackson Square", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.

Explore a world of travel with Expedia