"We had such a great stay, nice property,
Great location , the staff was helpful, friendly and fantastic! Delicious breakfast included … we really loved this place and we are looking forward to come back!"
"We had such a great stay, nice property,
Great location , the staff was helpful, friendly and fantastic! Delicious breakfast included … we really loved this place and we are looking forward to come back!"
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.
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.
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.
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.
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.
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.
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.
The service was over the top! From the front desk to the cleaning staff, everyone was friendly and always looking to do more. Room and hotel had a boutique feel that you don't see with the chain hotels. Also the location is ideal. One block off the action. Duval street is loud and crazy, but turn into the hotel and it suddenly becomes quite and comfortable. We will definitely be back
The service was over the top! From the front desk to the cleaning staff, everyone was friendly and always looking to do more. Room and hotel had a boutique feel that you don't see with the chain hotels. Also the location is ideal. One block off the action. Duval street is loud and crazy, but turn into the hotel and it suddenly becomes quite and comfortable. We will definitely be back
We had a fine stay. Our room was secluded. That is a good description. All the little balconies had a real secluded feel. Views to the other balconies were all obscured. Staff was game on. The cafe is recognized as one of the best restaurants on the island, get a dinner reservation well in advance of your stay.
We had a fine stay. Our room was secluded. That is a good description. All the little balconies had a real secluded feel. Views to the other balconies were all obscured. Staff was game on. The cafe is recognized as one of the best restaurants on the island, get a dinner reservation well in advance of your stay.
This was great place to stay and was in a great location. Every thing was in walking distance and was only about 100 yards off Duval Street yet on the hotel property the gardens made you feel like you were in the middle of nowhere. I would highly recommend this place and we stay there next time I am back in Key West.
This was great place to stay and was in a great location. Every thing was in walking distance and was only about 100 yards off Duval Street yet on the hotel property the gardens made you feel like you were in the middle of nowhere. I would highly recommend this place and we stay there next time I am back in Key West.
Anonymous traveler
Reviewed November 8, 2015Reviewed November 8, 2015
The room was clean and neat, everyone is very friendly and helpful. So glad we booked this place last minute. The best time we've ever had in Key west. You will not get anything more authentic than this place. Loved it!
The room was clean and neat, everyone is very friendly and helpful. So glad we booked this place last minute. The best time we've ever had in Key west. You will not get anything more authentic than this place. Loved it!
Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...
Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...
Beautiful property and amazing owners and staff. Very kind and generous. The property is perfectly located to Duval St. and lots of bars and restaurants. The pool is heated to a perfect temperature. The rooms are beautifully appointed and large. Just be aware that this is not an adult only property, so children can be a factor.
Beautiful property and amazing owners and staff. Very kind and generous. The property is perfectly located to Duval St. and lots of bars and restaurants. The pool is heated to a perfect temperature. The rooms are beautifully appointed and large. Just be aware that this is not an adult only property, so children can be a factor.
The Douglas House served as a perfect home base while in Key West. The location allows for easy access to all Duval has to offer. Really enjoyed being able to hear the national anthem being played every morning at 8 from the Navy base..
The Douglas House served as a perfect home base while in Key West. The location allows for easy access to all Duval has to offer. Really enjoyed being able to hear the national anthem being played every morning at 8 from the Navy base..
Anthony
Reviewed January 29, 2025Reviewed January 29, 2025
My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...
My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...
Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.
Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.
The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...
The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...
Sarah
Reviewed September 22, 2024Reviewed September 22, 2024
Wonderful trip. Great hotel but not for those who have issues with stairs unless they ask for one of the first floor rooms or bungalows. Would stay there again. Wish they served food though.
Wonderful trip. Great hotel but not for those who have issues with stairs unless they ask for one of the first floor rooms or bungalows. Would stay there again. Wish they served food though.
Keith
Reviewed December 9, 2024Reviewed December 9, 2024
We stayed here for one night for my husband's 40th birthday. The hotel was aware we were celebrating an occasion and offered complimentary refreshment's in our room. We were able to check on early, got upgraded to pool view and also checked out late!
When we arrived we were amazed with how huge the suite was. It was the same size as a condo. The decor was beautiful and the entire place was immaculate, including the outside. What we liked most was how quiet and relaxing the place was (there...
We stayed here for one night for my husband's 40th birthday. The hotel was aware we were celebrating an occasion and offered complimentary refreshment's in our room. We were able to check on early, got upgraded to pool view and also checked out late!
When we arrived we were amazed with how huge the suite was. It was the same size as a condo. The decor was beautiful and the entire place was immaculate, including the outside. What we liked most was how quiet and relaxing the place was (there...
Val
Reviewed January 23, 2017Reviewed January 23, 2017
The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area.
The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed!
Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...
The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area.
The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed!
Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...
The Mansion is within walking distance of everything you want to see/visit in Key West. No more than a 10-15 minute walk for everything from tourist attractions like Hemingway House and Key West Lighthouse, to a plethora of bars and restaurants.
The Mansion is within walking distance of everything you want to see/visit in Key West. No more than a 10-15 minute walk for everything from tourist attractions like Hemingway House and Key West Lighthouse, to a plethora of bars and restaurants.
ROBERT
Reviewed November 11, 2023Reviewed November 11, 2023
Friendly staff. Room was ready and clean.
Built in the 1800’s. Inground pool was a plus. One block off of Duvall St. and 7 blocks from The Mallory Square area.
Everything within walking distance.
Breakfasts were hearty and tasty.
We had a late afternoon flight out and we kept our room until we left since no one was checking in to that room on that day.
A cab for the airport was called for us which arrived right on time. A quaint place just blocks from the hustle and bustle of Key West. ...
Friendly staff. Room was ready and clean.
Built in the 1800’s. Inground pool was a plus. One block off of Duvall St. and 7 blocks from The Mallory Square area.
Everything within walking distance.
Breakfasts were hearty and tasty.
We had a late afternoon flight out and we kept our room until we left since no one was checking in to that room on that day.
A cab for the airport was called for us which arrived right on time. A quaint place just blocks from the hustle and bustle of Key West. ...
Phil
Reviewed January 16, 2018Reviewed January 16, 2018
Tucked into the very quiet Truman Annex, the Weatherstation Inn was a great find. It is an old house, built in 1911. If you enjoy old, quiet inns with reconfigured spaces, then this is the place for you. If you are looking for uniform, sleek and modern, then head on down the road. The continental breakfast was just right with delicious pastries from local bakery and the bed was comfy. Perhaps the most perfect aspect of the inn is the parking space where we parked our vehicle upon arrival and did...
Tucked into the very quiet Truman Annex, the Weatherstation Inn was a great find. It is an old house, built in 1911. If you enjoy old, quiet inns with reconfigured spaces, then this is the place for you. If you are looking for uniform, sleek and modern, then head on down the road. The continental breakfast was just right with delicious pastries from local bakery and the bed was comfy. Perhaps the most perfect aspect of the inn is the parking space where we parked our vehicle upon arrival and did...
Vibrant Atmosphere: Jackson Square offers a lively mix of tropical charm and rich history, making it a perfect spot for visitors.
Stunning Sunsets: Enjoy breathtaking sunsets at nearby parks like Mallory Square, known for its street performances.
Cultural Exploration: Discover historic houses, art galleries, and unique shops that showcase the local culture.
Live Jazz Performances: Experience captivating jazz music that enhances the vibrant ambiance of the area.
Diverse Accommodations: Choose from charming bed & breakfasts to luxurious resorts for a perfect stay.
Find great hotels near Jackson Square
Explore a variety of hotel accommodations in Jackson Square, Key West, Florida, where you can find everything from charming bed & breakfasts to luxurious resorts. This vibrant area is perfect for adventure seekers and couples looking for a romantic getaway, all while immersing themselves in the local history. Whether you're searching for top hotels or hidden gems, you'll discover excellent reviews and favorite spots that cater to your vacation needs.
La Concha Key West, Autograph Collection: Embrace the charm of Key West at La Concha, a 4-star hotel situated a mere 161m from Jackson Square. This property offers a welcoming atmosphere for families, pet owners, and LGBTQIA travelers, making it an inclusive retreat for all. The hotel features kid-friendly amenities such as cribs and window guards, ensuring a safe environment for little ones. Pets are also welcome, with specific policies in place to accommodate furry friends. Guests can enjoy a blend of classic and contemporary decor, a lively bar scene, and easy access to the vibrant local culture.
Opal Key Resort & Marina, Key West: Just 483m from Jackson Square, the Opal Key Resort & Marina stands out as a 4-star haven for adventure seekers and pet lovers alike. This resort offers an array of thrilling activities, including snorkeling, boat tours, and parasailing, perfect for those looking to explore the breathtaking waters of Key West. With pet-friendly policies and amenities that cater to dogs, this resort ensures that no family member gets left behind during your vacation. The stunning waterfront views and luxurious accommodations provide a perfect backdrop for relaxation after a day of adventure.
Heron House - Adult Only: Nestled only 322m from Jackson Square, Heron House is a charming 3.5-star bed and breakfast exclusively for adults. Ideal for LGBTQIA travelers and adventure enthusiasts, this property offers nearby activities such as sailing, kayaking, and windsurfing. With its intimate atmosphere, guests can unwind in beautifully appointed rooms while enjoying a relaxed, social environment. The B&B's commitment to providing personalized service and a tranquil retreat makes it a perfect choice for those seeking a peaceful getaway in the heart of Key West.
Where to stay near Jackson Square
Visitors to Jackson Square in Key West will be captivated by its vibrant atmosphere, blending tropical charm with rich history. Explore the nearby parks, such as Mallory Square, where you can enjoy stunning sunsets and lively street performances. The area is conveniently located, making it easy to wander through charming neighborhoods filled with art galleries and unique shops. Experience the perfect blend of adventure and relaxation in this must-visit tourist destination.
Key West: Nestled at the southernmost point of the continental United States, Key West is a vibrant island city renowned for its laid-back atmosphere and stunning coastal views. Visitors can immerse themselves in a variety of activities, from exploring local shops and dining at waterfront restaurants to indulging in water sports. The city is a hub for families, business travelers, and those seeking a unique urban experience. Key landmarks include the picturesque beaches and lively streets filled with art and culture, making it an ideal destination for all types of travelers.
Old Town Key West: Old Town Key West is a charming neighborhood brimming with historic charm and tropical character. Located in close proximity to Jackson Square, this area is perfect for leisurely strolls along its bustling streets lined with quaint shops, galleries, and restaurants. The atmosphere is vibrant, attracting families and business travelers alike. Visitors can experience the local culture while relaxing on family-friendly beaches or exploring the area's rich history, ensuring an enjoyable trip filled with excitement and discovery.
Key West Historic District: Just a short walk from Jackson Square, the Key West Historic District offers a glimpse into the island's storied past with its well-preserved architecture and historical landmarks. This neighborhood is popular for its city-themed experiences, making it a perfect spot for families and business travelers. Guests can explore charming streets that lead to inviting beaches and family-friendly recreational areas. With an array of shops and restaurants nearby, the Historic District provides a delightful blend of history and modern conveniences, ensuring a memorable visit.
Things to do near Jackson Square
Jackson Square in Key West offers a vibrant mix of activities for tourists, including stunning sunsets and lively festivals. Explore nearby museums and major attractions, or immerse yourself in the local nightlife. Don't miss out on captivating jazz performances that bring the area to life. Whether biking around the square or enjoying a leisurely stroll, there's something for everyone to enjoy in this iconic destination.
Shopping
Your shopping experience in Jackson Square includes We Cycle Key West, a bike shop 161m away, and The Kite House, a fun store 644m away. If you're up for a drive, visit the Big Pine Key Flea Market, located 46.7km away, for unique local finds.
Recreation
At Key West Golf Club, enjoy a refreshing round of golf surrounded by lush landscapes and a vibrant outdoor atmosphere, just 6.4km from Jackson Square. For a family-friendly experience, visit MLK Community Pool & Community Center, located 805m away, offering a fun and active environment for all ages.
Adventure
Jackson Square is a vibrant hub in Key West, surrounded by historic architecture and lively street performances. Explore local art galleries, enjoy delicious cuisine at nearby cafés, or join a guided ghost tour for a thrilling experience under the stars. Don't miss the stunning sunset views.
Nightlife
Experience the vibrant nightlife at Jackson Square with a visit to the Red Barn Theater, just 322m away, offering romance and entertainment. A short stroll to the Waterfront Playhouse (644m) and the Key West Burlesque Theater (1.1km) will immerse you in the local culture and fun.
*Distances are measured in a straight line; actual driving distances may vary depending on the route.
Booking tips and Expedia advantages for Jackson Square
To save money on your trip to Jackson Square, plan your visit between August and October when hotel prices are lower. Book your accommodations about a month in advance, and consider checking Expedia for last-minute deals, particularly on Tuesdays, which tend to be the cheapest days. Look for eco-certified hotels for sustainable options. Combine your hotel, flights, and activities into a package deal for additional savings. Finally, explore the area on foot to avoid transportation costs and enjoy free local attractions.
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: Utilize Expedia's search tool to refine your preferences, such as your budget, preferred location, and type of hotel you desire. For instance, selecting the Eco-certified option will reveal sustainable and environmentally-friendly hotels currently available. To find the best prices and deals, 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 deal.
Find the best attractions near Jackson Square
Jackson Square in Key West, Florida, offers a vibrant mix of historic houses, lively streets, and a modern square, perfect for culture enthusiasts and families alike. Visitors can explore nearby attractions, including iconic landmarks and local hotspots, while enjoying the rich history and vibrant atmosphere of this charming area. Don't miss the chance to experience the best of what Jackson Square has to offer.
Duval Street: Experience the vibrant energy of Duval Street, a popular thoroughfare filled with lively bars, eclectic shops, and delicious restaurants. This iconic street is perfect for leisurely strolls, where you can soak in the local atmosphere and enjoy the colorful street art.
Mallory Square: Known for its stunning sunsets, Mallory Square is a bustling hub of activity. Join the nightly Sunset Celebration, where street performers, artists, and food vendors create an unforgettable experience as the sun dips below the horizon.
Ernest Hemingway Home and Museum: Dive into literary history at the Ernest Hemingway Home and Museum. Explore the beautifully preserved residence and lush gardens, gaining insight into the life and works of one of America's greatest writers.
Best time to go to Jackson Square
The best time to visit Jackson Square is dependent 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 Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
71.1°F (21.7°C)
No Rain
Mostly Sunny
Average
Average
February
72.1°F (22.3°C)
No Rain
Mostly Sunny
Average
Slightly High
March
73.4°F (23.0°C)
No Rain
Mostly Sunny
Slightly High
Slightly High
April
76.8°F (24.9°C)
No Rain
Mostly Sunny
Average
Slightly High
May
79.3°F (26.3°C)
Light Rain
Mostly Sunny
Average
Average
June
82.6°F (28.1°C)
Light Rain
Mostly Sunny
Slightly High
Average
July
84.0°F (28.9°C)
Light Rain
Mostly Sunny
Slightly High
Average
August
84.4°F (29.1°C)
Light Rain
Mostly Sunny
Average
Slightly Low
September
83.7°F (28.7°C)
Light Rain
Mostly Sunny
Slightly Low
Slightly Low
October
80.8°F (27.1°C)
Light Rain
Mostly Sunny
Slightly Low
Slightly Low
November
76.6°F (24.8°C)
Light Rain
Mostly Sunny
Slightly Low
Average
December
73.9°F (23.3°C)
No Rain
Mostly Sunny
Average
Average
The nearest major airports for your trip to Jackson Square
To visit Jackson Square in Key West, Florida, you can fly into two major airports. Key West International Airport (EYW) is located 4.8km away, with nearby accommodation options such as the 5-star Casa Marina Key West, Curio Collection by Hilton, just 3.2km from the airport, and the 4-star Margaritaville Beach House Key West, only 1.6km away. Florida Keys Marathon Airport (MTH) is 78.9km from Jackson Square, offering hotels like the 4.5-star Isla Bella Beach Resort & Spa, 6.4km away, and Faro Blanco Resort & Yacht Club, also 4.8km from the airport. Both airports provide convenient access to local transportation services for easy travel to your hotel.
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 1672 hotels and other accommodations you'll find within a mile.
Where is the best place to stay close to Jackson Square?
How many hotels will I be able to find close to Jackson Square?
Expedia has 1672 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, 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.