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Top Hotels Close to Jackson Square

Our top choices for Jackson Square hotels

Almond Tree Inn Hotel - Adults Only

3.5 star property
10.0 out of 10, Exceptional, (1000)
"Wonderful little hotel that was relaxing with great breakfast. "
The price is CA $286
CA $322 total
includes taxes & fees
Sep 14 - Sep 15
Almond Tree Inn Hotel - Adults Only

The Marquesa Hotel

3.5 star property
9.8 out of 10, Exceptional, (1004)
"Property is nicely maintained staff is extremely attentive and polite"
The price is CA $263
CA $366 total
includes taxes & fees
Sep 8 - Sep 9
The Marquesa Hotel

Simonton Court Historic Inn & Cottages

2.5 star property
9.8 out of 10, Exceptional, (799)
"Enjoyed our stay. Highly recommend"
The price is CA $201
CA $227 total
includes taxes & fees
Aug 28 - Aug 29
Simonton Court Historic Inn & Cottages

Coco Plum Inn

3.0 star property
9.6 out of 10, Exceptional, (435)
"Great location, nice staff."
The price is CA $236
CA $266 total
includes taxes & fees
Sep 2 - Sep 3
Coco Plum Inn

Orchid Key Inn - Adults Only

3.5 star property
9.8 out of 10, Exceptional, (1000)
"Excellent friendly staff and beautiful property. "
The price is CA $278
CA $313 total
includes taxes & fees
Sep 7 - Sep 8
Orchid Key Inn - Adults Only

The Mermaid & Alligator

3.5 star property
9.8 out of 10, Exceptional, (256)
"Absolutely loved staying here and are already looking at dates to come back!"
The price is CA $263
CA $296 total
includes taxes & fees
Aug 26 - Aug 27
The Mermaid & Alligator

Island City House Hotel

3.0 star property
9.6 out of 10, Exceptional, (999)
"Beautiful grounds, good clean room, cold A/C, centrally located."
The price is CA $230
CA $259 total
includes taxes & fees
Aug 24 - Aug 25
Island City House Hotel

Duval House

3.0 star property
9.4 out of 10, Exceptional, (1015)
"Perfect location, adequate parking, delicious breakfast!"
The price is CA $123
CA $168 total
includes taxes & fees
Aug 26 - Aug 27
Duval House

H2O Suites - Adults Only

3.5 star property
9.8 out of 10, Exceptional, (549)
"I loved it here ! I will be booking again in the future."
The price is CA $360
CA $468 total
includes taxes & fees
Aug 25 - Aug 26
H2O Suites - Adults Only

Weatherstation Inn

2.5 star property
9.4 out of 10, Exceptional, (949)
"The staff went above and beyond for us to have a great vacation and stay! "
The price is CA $235
CA $264 total
includes taxes & fees
Aug 24 - Aug 25
Weatherstation Inn

Ambrosia Key West

3.5 star property
9.4 out of 10, Exceptional, (1001)
"Loved the Ambrosia and would definitely stay here again. Location is excellent, very walkable, we didnt need our car for the entire stay. Hotel is quiet and staff are very welcoming. "
The price is CA $212
CA $238 total
includes taxes & fees
Sep 1 - Sep 2
Ambrosia Key West

Marrero's Guest Mansion

3.5 star property
9.4 out of 10, Exceptional, (333)
"The vibes were right! Room #12 in the back poolside solo cottage is fire!! 🔥✌️🧘‍♀️😘 "
The price is CA $277
CA $311 total
includes taxes & fees
Aug 26 - Aug 27
Marrero's Guest Mansion

Westwinds Inn

3.5 star property
9.4 out of 10, Exceptional, (1001)
"Great location and clean rooms with cold AC! Very charming property! "
The price is CA $219
CA $246 total
includes taxes & fees
Aug 24 - Aug 25
Westwinds Inn

Ella's Cottages - Key West Historic Inns

3.5 star property
9.4 out of 10, Exceptional, (367)
"Loved our stay. "
The price is CA $282
CA $388 total
includes taxes & fees
Aug 25 - Aug 26
Ella's Cottages - Key West Historic Inns

The Grand Guesthouse

2.5 star property
9.6 out of 10, Exceptional, (1000)
"Nice homey atmosphere "
The price is CA $176
CA $233 total
includes taxes & fees
Aug 24 - Aug 25
The Grand Guesthouse

Santa Maria Suites

4.0 star property
9.6 out of 10, Exceptional, (1004)
"Best place to stay great staff and the rooms are beautiful "
The price is CA $361
CA $469 total
includes taxes & fees
Sep 2 - Sep 3
Santa Maria Suites

Opal Key Resort & Marina, Key West

4.0 star property
9.2 out of 10, Wonderful, (1007)
"Great stay! "
The price is CA $360
CA $460 total
includes taxes & fees
Aug 24 - Aug 25
Opal Key Resort & Marina, Key West

The Garden House

3.0 star property
9.2 out of 10, Wonderful, (649)
"Nice Location Fantastic Staff Clean, comfortable room"
The price is CA $134
CA $180 total
includes taxes & fees
Aug 24 - Aug 25
The Garden House

Paradise Inn Key West - Adults Only

3.5 star property
9.2 out of 10, Wonderful, (1000)
"Great hotel we have stayed here several times and love it every time. "
The price is CA $179
CA $264 total
includes taxes & fees
Sep 2 - Sep 3
Paradise Inn Key West - Adults Only

Heron House - Adult Only

3.5 star property
9.0 out of 10, Wonderful, (1132)
"Beautiful and quaint little place to stay. Just a couple blocks from the main Street, so we walked the whole time. The staff was super friendly, the room was clean, and the breakfast was good. Will def stay again!"
The price is CA $160
CA $226 total
includes taxes & fees
Aug 26 - Aug 27
Heron House - Adult Only
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.

Top Jackson Square Hotel Reviews

Hotels near Other Key West Attractions

Find out more about Jackson Square

Find out more about Jackson Square

Top reasons to visit Jackson Square

  • Vibrant Atmosphere: Jackson Square offers a lively blend of historical charm and tropical allure, perfect for immersing yourself in local culture.
  • Breathtaking Sunsets: Enjoy stunning sunsets that paint the sky in vibrant colours, making for a picturesque experience.
  • Cultural Events: Attend lively festivals and events that showcase the unique culture and heritage of Key West.
  • Outdoor Activities: Stroll through nearby parks like Fort Zachary Taylor Historic State Park for beautiful views and rich history.
  • Diverse Accommodations: Choose from a range of lodging options, from cozy bed and breakfasts to upscale hotels, catering to all preferences.

Find great hotels near Jackson Square

Discover a variety of hotel accommodations in the charming Jackson Square, Key West, Florida, catering to every budget and preference. With options ranging from cozy bed and breakfasts to well-appointed hotels, visitors can enjoy a comfortable stay while exploring the vibrant local culture. Whether you're seeking adventure, a pet-friendly getaway, or a business trip, Jackson Square has the perfect lodging to enhance your experience in this picturesque destination.

  • La Concha Key West, Autograph Collection: Immerse yourself in the vibrant spirit of Key West at La Concha Key West, Autograph Collection. This 4-star hotel is a mere 161m from Jackson Square, making it an ideal choice for those seeking a beach, family, or adventure-themed vacation. With direct access to the beach, you can soak up the sun and partake in various water sports. The hotel offers a range of adventure activities nearby, including kayaking, bicycle rentals, Segway tours, windsurfing, and sailing. Families will appreciate the thoughtful amenities for children, such as complimentary cribs and window guards, ensuring a safe and enjoyable stay for all guests.
  • Opal Key Resort & Marina, Key West: Located 483m from Jackson Square, Opal Key Resort & Marina, Key West is perfect for travellers who crave adventure and wish to bring their furry friends along. This 4-star resort features a stunning marina and offers a variety of onsite activities, including boat tours, snorkeling, and parasailing. If you prefer to explore on foot or on two wheels, hiking and biking trails are available nearby. The pet-friendly policy allows dogs (with certain restrictions) and waives fees for service animals, making it a welcoming spot for all. Guests rave about the blend of relaxation and adventure that this resort provides.
  • Heron House - Adult Only: Designed exclusively for adults, Heron House offers a tranquil retreat just 322m from Jackson Square. This charming 3.5-star bed and breakfast caters to adventure seekers looking for a unique experience. With various activities available nearby, including fishing, waterskiing, surfing, and windsurfing, guests can indulge in the thrill of water sports. The relaxed atmosphere combined with personalized service makes it an ideal choice for couples or solo travellers looking to unwind after a day of adventure. Enjoy the intimate setting and explore the beautiful surroundings at your leisure.

Where to stay near Jackson Square

Visitors to Jackson Square, Key West, will be captivated by its vibrant atmosphere, blending historical charm with tropical allure. Explore the nearby lush parks like Fort Zachary Taylor Historic State Park, offering stunning water views and rich history. Enjoy luxury accommodations in the heart of the action, and indulge in diverse excursions that highlight the region’s adventure and natural beauty. Experience the unique vibe of this iconic location, where every corner tells a story.

  • Key West: Nestled as an island city, Key West is a vibrant destination that offers a seamless blend of relaxation and excitement. Jackson Square serves as a central point for visitors, making it easy to explore the area. Travellers flock to Key West year-round, with peak visits in January, March, and September. Here, families, business travellers, and city explorers will find plenty to do, including shopping at local malls and enjoying the beautiful beaches. Don't miss the lively streets filled with unique shops and cultural landmarks that showcase the island's rich history.
  • Old Town Key West: A charming neighbourhood, Old Town Key West is known for its historic architecture and laid-back atmosphere. Jackson Square is located within this area, making it a convenient hub for exploration. Visitor numbers peak in March, July, and December, drawing those seeking a blend of family fun and city experiences. The neighbourhood boasts a variety of shopping areas and resorts, alongside beautiful beaches perfect for family outings. Strolling through its picturesque streets, you'll discover an array of local eateries and unique shops that reflect the island’s vibrant culture.
  • Key West Historic District: Located a mere 483m from Jackson Square, the Key West Historic District is a treasure trove of history and charm. This neighbourhood attracts a steady stream of visitors throughout the year, with peaks in March, July, and December. Families, business travellers, and city adventurers are drawn to the area for its shopping options and nearby resorts. Notable attractions include scenic streets and stunning family-friendly beaches, offering the perfect blend of relaxation and cultural exploration. Walking through this district, you’ll be captivated by the historic homes and lush landscapes that define its character.

Things to do near Jackson Square

Jackson Square in Key West offers a variety of activities, including enjoying breathtaking sunsets and attending lively festivals. You can take a pleasant stroll through Jackson Square Park, explore the local golf course, and participate in tours available on Mondays. It's an inviting events venue, perfect for immersing yourself in the local culture and enjoying the vibrant atmosphere that the area has to offer.

Shopping

In Jackson Square, visit The Kite House, a charming store just 644m away, and We Cycle Key West, located only 161m away. If you're up for a drive, check out the Big Pine Key Flea Market, which is 46.7km away and offers a unique local vibe.

Recreation

Key West Golf Club, located 6.4km from Jackson Square, offers a relaxing outdoor experience with stunning greens and a vibrant atmosphere. For family-friendly fun, visit the MLK Community Pool & Community Center, just 805m away, where you can enjoy swimming and various recreational activities.

Nightlife

The nightlife in Jackson Square offers a vibrant mix of culture and entertainment. Catch a show at the Waterfront Playhouse, located 644m away, or enjoy the unique performances at the Key West Burlesque Theater, 1.1km away. Don't miss the charm of the Red Barn Theater, just 322m away!

Booking tips and Expedia advantages for Jackson Square

To save money during your visit to Jackson Square, consider exploring free attractions like Duval Street, Mallory Square, and the Southernmost Point. Plan your trip between August and October for lower accommodation prices, and book your hotel about a month in advance for the best rates. Look for last-minute deals on Expedia, particularly on Tuesdays, which tend to be the cheapest days to stay. Combine your hotel, flights, and activities through Expedia packages for additional savings, and use their search tool to filter options based on your budget and preferences.

  • 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: The cheapest time to book a hotel around Jackson Square is usually 1 month out from when you are planning to stay. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
  • 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: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred type of accommodation. To find the most affordable prices and offers, simply arrange the price filter from lowest to highest.
  • 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.

Find the best attractions near Jackson Square

Jackson Square in Key West, Florida, offers a vibrant mix of historic sites, lively streets, and modern squares, perfect for travellers seeking culture and family experiences. Key attractions include the iconic Jackson Square itself, along with nearby tourist spots that showcase the area's rich heritage. Whether you're exploring the charm of Jackson Square or venturing to Jackson Hole, there's plenty to see and do in this beautiful locale.

  • Duval Street: Experience the vibrant heart of Key West on Duval Street, a lively thoroughfare filled with shops, bars, and restaurants. Just 161m from Jackson Square, it offers a unique blend of local culture and festive atmosphere, perfect for strolling and people-watching.
  • Mallory Square: Located 644m away, Mallory Square is famous for its sunset celebrations. As a modern square, it hosts street performers, local artisans, and food vendors, creating a lively scene that captures the essence of Key West's community spirit.
  • Ernest Hemingway Home and Museum: Just 483m from Jackson Square, this historic house invites you to explore the life of the famed author. Immerse yourself in the rich culture and history as you tour the beautifully preserved home and gardens.

Best time to go to Jackson Square

Visitor numbers around Jackson Square is generally unchanged in popularity throughout the year. The best time to visit Jackson Square is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnyAverageSlightly High
March73.4°F (23.0°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly 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 Rain (Dry)Mostly SunnySlightly HighAverage

The nearest major airports for your trip to Jackson Square

To reach Jackson Square in Key West, Florida, you can fly into Key West International Airport (EYW), located 4.8km away. Nearby accommodations include the 5-star Casa Marina Key West, just 3.2km from the airport, and the 4-star Margaritaville Beach House Key West, only 1.6km away. Both hotels provide convenient access to the airport. Another option is Oceans Edge Key West Resort, also 3.2km from EYW. Alternatively, you can fly into Florida Keys Marathon Airport (MTH), situated 78.9km from Jackson Square, with nearby hotels like the 4.5-star Isla Bella Beach Resort & Spa, 6.4km from MTH, and Tranquility Bay Beachfront Hotel, 4.8km away.

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 biking. If you're looking for a convenient place to stay, check out the 1762 hotels and other accommodations you'll find within a mile.

Where is the best place 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 traveler data, and this hotel offers 3 restaurants and 2 bars. Other good options close by include Hyatt Centric Key West Resort and Spa and Southernmost Beach Resort and Guesthouses.

How many hotels will I be able to find close to Jackson Square?

Expedia has 1762 hotels and other accommodations 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! The majority of hotel bookings are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to review the best deals near Jackson Square.

Where can I learn more about changing or cancelling my trip in the area near Jackson Square?

For more information about updating your stay near Jackson Square or cancelling it, click here.

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 Saint Mary Star of the Sea 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.