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2026-02-26
2026-02-27
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Hotels in Key West near Jackson Square

Hyatt Vacation Club At Sunset Harbor

200 Sunset Lane, Key West, United States View map

The luxurious Hyatt Residence Club Key West is Sunset Harbor, an oasis nestled in the heart of Old Town Key West. Immerse yourself in the relaxed Key West lifestyle as you enjoy the resort's prime… More

From US$ 512 Book Now

Casa Loca

535 Petronia Street, Key West, United States View map

At the 2-bedroom Casa Loca Villa Key West, guests can enjoy canoeing, hiking, and cycling as well as a location just 5 minutes' walk from The Ernest Hemingway Home and Museum. More

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Duval Street Suite W Parking And Pool

824 Duval Street, Key West, United States View map

Set right in the centre of Key West, the 37 m^2 Duval Street Suite W Parking And Pool Key West is about a 15-minute walk from Key West Aquarium. More

From US$ 636 Book Now

Duval Street Suite With Pool

Duval Street 824, Key West, United States View map

The Duval Street Suite With Pool is a refined retreat located in the heart of Key West. Just 200 metres from the iconic Ernest Hemingway Home and Museum, this exquisite accommodation places you at… More

From US$ 1091 Book Now

Duval Street Suite Overlooking Duval With Parking And Pool

824 Duval Street, Key West, United States View map

Located in the Duval district with The Ernest Hemingway Home and Museum nearby, the 1-bedroom Duval Street Suite Overlooking Duval With Parking And Pool lies a mere 10 minutes' stroll from South… More

From US$ 763 Book Now

Duval Street Suite Overlooking Duval W Parking And Pool

Duval Street 824, Key West, United States View map

To enjoy your vacation in Key West, stay at the 1-room Duval Street Suite Overlooking Duval W Parking And Pool Key West, which is only 1.2 km from Front Street and around 800 metres from San Carlos… More

From US$ 421 Book Now

Duval Street Suite W Parking And Heated Pool

824 Duval Street, Key West, United States View map

To enjoy your vacation in Key West, stay at the 1-room Duval Street Suite W Parking And Heated Pool Key West, which is at a distance of 2.4 km from Higgs Beach Dog Park and merely 9 minutes' stroll… More

From US$ 636 Book Now

6 Bedroom 6 Bath Guesthouse On Duval Street

824 Duval Street, Key West, United States View map

The 5-bedroom 6 Bedroom 6 Bath Guesthouse On Duval Street is located 15 minutes on foot from Simonton Street and within 5 minutes' walk of The Ernest Hemingway Home and Museum. The Key West villa… More

From US$ 3636 Book Now

Duval Street Suite W Kitchen And Shared Heated Pool

824 Duval Street, Key West, United States View map

Located 7 minutes' walk from Duval Street and The Ernest Hemingway Home and Museum, Duval Street Suite W Kitchen And Shared Heated Pool Key West features views of the city. Situated within close… More

From US$ 501 Book Now

Two Duval Street Suites W Pool

Duval Street 824, Key West, United States View map

The spacious 2-bedroom Two Duval Street Suites W Pool Key West is situated right in the centre of Key West, nearly a 5-minute walk from Key West Lighthouse and Keeper's Quarters Museum. More

From US$ 979 Book Now

Two Duval Street Suites W Parking And Pool

Duval Street 824, Key West, United States View map

Situated in the vibrant heart of Duval Street, Two Duval offers an exceptional escape steeped in the spirit of the Florida Keys. This premier destination is designed to provide guests with an… More

From US$ 807 Book Now

Two Duval Street Condos W Parking And Pool

Duval Street 824, Key West, United States View map

Boasting the location 1.2 km from Simonton Street, the 2-bedroom Two Duval Street Condos W Parking And Pool is also at 150 metres of The Ernest Hemingway Home and Museum. Located in the Duval… More

From US$ 834 Book Now

Three Duval Street Suites W Parking And Pool

824 Duval Street, Key West, United States View map

Situated only 250 metres from The Ernest Hemingway Home and Museum, the 3-bedroom Three Duval Street Suites W Parking And Pool Key West villa ensures a great leisure experience by offering cycling… More

From US$ 2562 Book Now

Four Suites On Duval Street W Parking And Pool

Duval Street 824, Key West, United States View map

The spacious 4-bedroom Four Suites On Duval Street W Parking And Pool Key West is situated right in the centre of Key West, nearly a 5-minute walk from Key West Lighthouse and Keeper's Quarters… More

From US$ 1630 Book Now

Classic King With Balcony At Curry Mansion

Caroline Street 511, Key West, United States View map

**Welcome to the Classic King With Balcony at Curry Mansion, your serene haven in the heart of Key West.** This enchanting retreat merges contemporary comforts with historic charm, situated perfectly… More

From US$ 631 Book Now

King Suite At Curry Mansion With Heated Pool!

Caroline Street 511, Key West, United States View map

Located merely 450 metres from Key West Aquarium, King Suite At Curry Mansion With Heated Pool! Key West hotel is a 7-minute stroll from San Carlos Institute. This Key West inn provides Wi-Fi… More

From US$ 697 Book Now

King Suite Balcony - At James House

Caroline Street 511, Key West, United States View map

King Suite Balcony - At James House Key West hotel, located merely 9 minutes' walk from Duval Street and within 10 minutes' drive of Smathers Beach, features an outdoor swimming pool for guests to… More

From US$ 242 Book Now

Classic King Balcony At The James House

Caroline Street 511, Key West, United States View map

**Welcome to the Classic King Balcony at The James House** in the heart of Key West. This charming retreat is ideally located just 500 meters from the pristine Simonton Street Beach, offering guests… More

From US$ 561 Book Now

Deluxe Queen At The Curry Mansion - Parking & Heated Pool!

Caroline Street 511, Key West, United States View map

Deluxe Queen At The Curry Mansion - Parking & Heated Pool! Hotel Key West, located only 9 minutes' walk from Duval Street, offers an outdoor pool and Wi-Fi throughout the property. The inn is a good… More

From US$ 533 Book Now

Deluxe King - Curry Mansion With Pool!

Caroline Street 511, Key West, United States View map

Featuring a patio and an outdoor pool, Deluxe King - Curry Mansion With Pool! Hotel Key West lies 17 minutes' walk from USCGC Ingham Maritime Museum. Wi-Fi is available throughout the property. More

From US$ 318 Book Now

Classic King- Curry Mansion With Heated Pool!

Caroline Street 511, Key West, United States View map

Classic King- Curry Mansion With Heated Pool! Hotel Key West, located about 10 minutes' drive from West Martello Tower, offers an outdoor swimming pool and Wi-Fi throughout the property. The inn is a… More

From US$ 694 Book Now

Deluxe King With Balcony - At James House With Parking!

Caroline Street 511, Key West, United States View map

Deluxe King With Balcony - At James House With Parking! Hotel Key West, located 7 minutes' walk from Mile Marker 0 Store, offers an outdoor swimming pool and Wi-Fi throughout the property. The inn is… More

From US$ 763 Book Now

Classic Queen - Curry Mansion With Heated Pool

Caroline Street 511, Key West, United States View map

Classic Queen - Curry Mansion With Heated Pool Hotel Key West, located about 5 minutes on foot from Mel Fisher Maritime Heritage Museum, offers an outdoor swimming pool and Wi-Fi throughout the… More

From US$ 403 Book Now

Blue Room At The Grand Maloney

Caroline Street 529, Key West, United States View map

Featuring a patio and an outdoor swimming pool, Blue Room At The Grand Maloney Key West hotel lies 25 minutes' stroll from Higgs Beach Dog Park. The inn provides guests with Wi-Fi throughout the… More

From US$ 516 Book Now

Green Room At The Grand Maloney

Caroline Street 529, Key West, United States View map

Located around 500 metres from Key West Aquarium, Green Room At The Grand Maloney Key West hotel includes an outdoor swimming pool and a patio. The inn provides guests with Wi-Fi throughout the… More

From US$ 673 Book Now

Bunk Room At The Grand Maloney

Caroline Street 529, Key West, United States View map

Bunk Room At The Grand Maloney Key West hotel, located 550 metres from Mallory Square and 0.6 km from Jackson Square, features an outdoor swimming pool for guests to take a dip in. Wi-Fi is offered… More

From US$ 768 Book Now

Yellow Room At Grand Maloney

Caroline Street 529, Key West, United States View map

**Discover an Oasis in the Heart of Key West** Nestled amidst the vibrant energy of downtown Key West, the Grand Maloney offers a contemporary retreat in a historically restored two-story brick home. More

From US$ 680 Book Now

Carriage House At Grand Maloney

Caroline Street 529, Key West, United States View map

Carriage House At Grand Maloney Hotel Key West, located just a 7-minute walk from Mallory Square and merely 500 metres from Nancy Forrester's Secret Garden, features an outdoor swimming pool for… More

From US$ 459 Book Now

Takeover At The Grand Maloney

Caroline Street 529, Key West, United States View map

Located right in the centre of Key West, The Grand Maloney Hotel- Great For Large Groups! offers fast access to Key West Aquarium, which helps break from routine and stands just 350 metres away. More

From US$ 4224 Book Now

The Bartlum-Luxurious Studio

533 Caroline Street, Key West, United States View map

To enjoy your vacation in Key West, stay at the 1-room The Bartlum-Luxurious Studio Apartment Key West, which is a 17-minute stroll from USCGC Ingham Maritime Museum and about 5 minutes by car from… More

From US$ 186 Book Now

Creme Brulee Suite

Caroline Street 537, Key West, United States View map

Creme Brulee Suite Key West hotel, located around 20 minutes' walk from Southernmost Point, features Wi-Fi throughout the property. This inn also includes a patio with a barbeque grill. More

From US$ 223 Book Now

Key Lime Cottage

Caroline Street 537, Key West, United States View map

Located within 5 minutes' drive of Ripley's Believe It or Not Museum, Key Lime Cottage Key West hotel includes an outdoor swimming pool and a patio. Wi-Fi is offered throughout the property at this… More

From US$ 363 Book Now

Honey Bun Hideaway

Caroline Street 537, Key West, United States View map

Honey Bun Hideaway Hotel Key West, located merely 400 metres from Ripley's Believe It or Not Museum, offers an outdoor pool, Wi-Fi throughout the property. The inn is within walking distance of many… More

From US$ 237 Book Now

Sugar Pie Suite

Caroline Street 537, Key West, United States View map

Sugar Pie Suite Key West hotel, located about 5 minutes by car from Fort Zachary Taylor, offers an outdoor swimming pool, Wi-Fi throughout the property. The inn is a good starting point for exploring… More

From US$ 486 Book Now

Banana Split

Caroline Street 537, Key West, United States View map

For those traveling to the area, the nearest airport is conveniently located just 4 km away, ensuring an easy arrival and departure. More

From US$ 383 Book Now

Sweet Caroline

Caroline Street 537, Key West, United States View map

Sweet Caroline Villa offers accommodation just 400 metres from Simonton Beach, while Key West Aquarium is about a 5-minute stroll away. This villa is equipped with 2 bedrooms plus a kitchen with a… More

From US$ 932 Book Now

Bananas Foster Guesthouse

Caroline Street 537, Key West, United States View map

Set close to The Oldest House, the 7-bedroom Bananas Foster Guesthouse is merely 650 metres from Duval Street. The villa provides guests with free parking and an outdoor swimming pool in the Duval… More

From US$ 4595 Book Now

Bahama Dreams

903 Thomas Street, Key West, United States View map

The 2-bedroom Bahama Dreams Villa Key West is located just 1.5 km from Key West First Legal Rum Distillery and allows guests to enjoy windsurfing, snorkelling, and canoeing. Featuring a patio, this… More

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Tranquility On Ann Street

219 Ann Street #1, Key West, United States View map

The 1-bedroom Tranquility On Ann Street Villa Key West entices guests to enjoy windsurfing, snorkelling, and canoeing and offers proximity to Key West First Legal Rum Distillery, located just 8… More

From US$ 931 Book Now

Bali Hideaway

217 Ann Street Rear, Key West, United States View map

Escape to the Bali Hideaway, a tranquil oasis nestled in the vibrant heart of Duval Street. This exquisite villa invites you to indulge in an authentic Key West experience, where island-inspired… More

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Casa Avila By Last Key Realty

625 Eaton Street, Key West, United States View map

The 3-bedroom Casa Avila By Last Key Realty Key West offers proximity to such city sites as Papa's Pilar Rum Distillery, located merely a 6-minute walk away. More

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The Duke And The Queen By Last Key Realty

512 Catherine Street #2 & 515 Louisa Street, Key West, United States View map

Offering a Jacuzzi for a relaxing experience, The Duke And The Queen By Last Key Realty Key West villa is located a 14-minute walk from Mel Fisher Maritime Heritage Museum. More

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Ann Street Cottage

219 Ann Street #2, Key West, United States View map

The 2-bedroom Ann Street Cottage Key West is located only a 6-minute walk from The Studios of Key West Cultural Association and offers guests to relish a patio as well as a heated swimming pool. At… More

From US$ 711 Book Now

Seascape Tropical Inn (Adults Only)

420 Olivia Street, Key West, United States View map

For those wanting to explore, Seascape's concierge is ready to provide personalized recommendations. More

From US$ 130 Book Now

Namaste

219 Ann Street Rear, Key West, United States View map

The 2-bedroom Namaste Villa Key West is located about a 25-minute walk from Southernmost Point and provides windsurfing, snorkelling, and canoeing for active guests. More

From US$ 828 Book Now

Courtney'S Place Historic Cottages & Inns

720 Whitmarsh Lane, Key West, United States View map

Located 2.8 km from Smathers Beach, the 2-star Courtney'S Place Historic Cottages & Inns Key West offers Wi-Fi in public areas and parking. Boasting a swimming pool, this Key West hotel is nestled at… More

From US$ 279 Book Now

Mesa House, Uno-Perfect Location

Simonton Street 220, Key West, United States View map

To enjoy your vacation in Key West, stay at the spacious 74 m^2 Mesa House, Uno-Perfect Location Apartment Key West, which is just 1.4 km from Florida Keys Eco-Discovery Center and within a 5-minute… More

From US$ 474 Book Now

Mesa House, Dos -Unreal Location

Simonton Street 220, Key West, United States View map

The spacious 1-bedroom Mesa House, Dos -Unreal Location Apartment Key West is situated right in the centre of Key West, only 6 minutes' walk from Nancy Forrester's Secret Garden. This 65 m^2… More

From US$ 565 Book Now

The Mesa House-Close To Duval!

Simonton Street 220, Key West, United States View map

The 3-bedroom Mesa House Villa is nearly 8 minutes on foot from Truman Little White House and walking distance from the bustling plaza "Mallory Square". A fully furnished kitchen with a microwave… More

From US$ 1379 Book Now

Caroline On My Mind

616 Caroline St #4, Key West, United States View map

The 2-bedroom Caroline On My Mind Villa Key West is located just 300 metres from Key West Historic Seaport and features a swimming pool as well as a terrace for guests' pleasure. More

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