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2026-04-18
2026-04-19
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Hotels in Key West near Flagler Station Oversea Railway

Casa Rosa

331 Simonton Street, Key West, United States View map

Casa Rosa Villa Key West is located only a 6-minute walk from the Papa's Pilar Rum Distillery and features a swimming pool and a patio for a relaxing stay. This property is situated within reach of… More

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Eden House

1015 Fleming Street, Key West, United States View map

The Eden House is the original Key West hotel laden with art-deco designs and nestled amid lush landscapes. This historic hotel offers a peaceful haven amid beautiful surroundings and brims with… More

From US$ 235 Book Now

Heron House Court (Adults Only)

412 Frances St, Key West, United States View map

With Key West International Airport a mere 10 km away, and easily accessible trolley and walking tours available, Heron House and Heron House Court redefine your Key West experience, blending… More

From US$ 339 Book Now

Rigby House - Brand New With Private Pool

Simonton Street 218, Key West, United States View map

**Welcome to Rigby House - Brand New With Private Pool Villa Key West**, your ultimate tropical escape nestled in the vibrant heart of Duval Street. This stunning retreat is freshly established and… More

From US$ 3023 Book Now

The Inn On Fleming

1016 Fleming St., Key West, United States View map

**Discover Tranquility at The Inn on Fleming, Key West** More

From US$ 347 Book Now

Simonton Court Historic Inn & Cottages

320 Simonton Street, Key West, United States View map

**Welcome to Simonton Court Historic Inn & Cottages, a charming haven nestled in the heart of Key West.** This quaint property stretches over two acres, offering a serene retreat characterized by… More

From US$ 175 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

The Geiger Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

At The Geiger Suite At Inn On Fleming Key West! villa, guests can enjoy windsurfing, snorkelling, and fishing as well as a location 700 metres from the Key West Cemetery. More

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The Simonton Room At Inn On Fleming Key West

1016 Fleming St., Key West, United States View map

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From US$ 415 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

The Gato Room At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

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From US$ 424 Book Now

The Truman Room At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

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The Cornish Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

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The Mallory Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

Along with proximity to the 19 - acre Key West Cemetery, just a 9-minute walk away, The Mallory Suite At Inn On Fleming Key West! villa offers opportunities for windsurfing, snorkelling, and fishing… More

From US$ 441 Book Now

The Hemingway Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

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The Whitehead Room At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

During the stay at The Whitehead Room At Inn On Fleming Key West! villa, guests can indulge in windsurfing, snorkelling, and fishing or visit the USCGC Ingham Maritime Museum, located a 25-minute… More

From US$ 540 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

The Flagler Room At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

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From US$ 452 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

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$ 416 Book Now

First Breath By Avantstay Close To Old Town W Pool Month Long Stays Only

1106 Eaton Street, Key West, United States View map

The 3-bedroom villa is just 1.2 km from Truman Little White House and less than 10 minutes on foot from from the Minor Saint Mary Star of the Sea Basilica. Guests, staying at this villa, can use an… More

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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

Ambrosia Key West

622 Fleming Street, Key West, United States View map

Welcome to the alluring charm of the Ambrosia Key West Bed & Breakfast, an enchanting paradise nestled in the heart of the city. This property offers a unique blend of Victorian elegance and modern… More

From US$ 299 Book Now

Seaport Sensation By Last Key Realty

121 Simonton Street, Key West, United States View map

Seaport Sensation By Last Key Realty Key West villa offers swift access to various city sites, such as Caroline Street, situated about 5 minutes' walk away. More

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Galleon Resort And Marina

617 Front Street, Key West, United States View map

The 3-star Galleon Resort And Marina Key West is located 10 km from Key West International airport and offers a swimming pool as well as a fitness club. Nestled in the Downtown Key West district of… More

From US$ 285 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$ 555 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$ 568 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 Artist House

534 Easton Street, Key West, United States View map

Featuring bicycle rentals, as well as Wi-Fi in public areas, The Artist House Bed & Breakfast Key West is only 9 minutes' walk from Key West Aquarium. The bed & breakfast lies only minutes from Duval… More

From US$ 125 Book Now

The Zesty Lime By Last Key Realty

421 Simonton Street, Key West, United States View map

The Zesty Lime By Last Key Realty Key West villa is located just 1.8 km from USCGC Ingham Maritime Museum and provides a private swimming pool, ensuring a relaxing stay. More

From US$ 2356 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

Sans Souci

1110 Elgin Lane, Key West, United States View map

During the stay at Sans Souci Villa Key West, guests can indulge in windsurfing, snorkelling, and canoeing or visit South Beach, located 25 minutes' walk away. More

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The Lime And The Coconut By Last Key Realty

421-423 Simonton Street, Key West, United States View map

Staying at the 8-bedroom The Lime And The Coconut By Last Key Realty Key West villa, guests can visit The Ernest Hemingway Home and Museum, which is only 1.4 km away. More

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New Coastal Rose - Bright Loft With High Ceilings

Rose Lane 526, Key West, United States View map

Located 8 minutes on foot from Key West First Legal Rum Distillery and Key West Express, the spacious 84 m^2 New Coastal Rose - Bright Loft With High Ceilings Apartment Key West features views of the… More

From US$ 858 Book Now

New Rose Petal Petite Suite - Pool & Parking

Rose Lane 526, Key West, United States View map

To enjoy your vacation in Key West, stay at the spacious 74 m^2 New Rose Petal Petite Suite - Pool & Parking Key West, which is within a 5-minute drive of Higgs Beach Dog Park and just 650 metres… More

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New Rose Retreat - Pool & Parking

Rose Lane 526, Key West, United States View map

The 2-bedroom New Rose Retreat - Pool & Parking Villa Key West entices guests to enjoy cycling and fisheries and offers proximity to Key West First Legal Rum Distillery, located merely an 8-minute… More

From US$ 741 Book Now

The Toasted Coconut By Last Key Realty

423 Simonton Street, Key West, United States View map

Featuring a swimming pool for guests' enjoyment, The Toasted Coconut By Last Key Realty Key West villa is nestled right in the centre of Key West, about a 25-minute walk from South Beach. More

From US$ 798 Book Now

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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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

Blanco Luxury Villa

129 Simonton St, Key West, United States View map

Offering a terrace overlooking the city, Blanco Luxury Villa Key West is located just a 6-minute walk from the Papa's Pilar Rum Distillery. More

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Maison Tropicale By Last Key Realty

510 Frances Street, Key West, United States View map

**Experience Island Luxury at Maison Tropicale** More

From US$ 367 Book Now