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The historic Key West lighthouse

Lighthouse Hotel

 Private. Unexpected. Unmistakably Key West.

Just steps from the iconic Key West Lighthouse and the Ernest Hemingway Home & Museum, Lighthouse Hotel pairs historic character with thoughtful design and warm, personalized hospitality. Thoughtful gathering spaces, genuine service, and meaningful details create a stay that feels welcoming, effortless, and entirely your own.

 

 

The historic Key West lighthouse

Stay With Us

Historic charm meets laid-back island living in rooms full of character, comfort, and a little Old Town personality.

The Group Gathers. You Get the Suite.
Explore the Hemingway King Suite

 

  • Lighthouse Hotel Pool
Eat + drink

Isabel’s

Restaurant and Bar

Steps from the legendary Hemingway Home & Museum, Isabel’s is Lighthouse Hotel’s inviting poolside bar and a favorite place to gather throughout the day. Start your morning with a specialty coffee and complimentary breakfast, then return for a relaxed lunch, handcrafted cocktails, and island-inspired favorites in a tropical setting.

No visit is complete without a classic mojito, famously one of Ernest Hemingway’s favorite cocktails during his years in Key West. Just moments from the home where he lived and wrote many of his most celebrated works, Isabel’s offers the perfect place to raise a glass and experience a piece of the island’s literary history while soaking up the laid-back atmosphere of Old Town.

 

A Little Sun, A Little Scandal

Across from Hemingway’s legendary home, Lighthouse Hotel has a few stories of its own. Legend has it that Isabel, Hemingway’s seamstress and rumored mistress, once lived here. Today, her story lives on at Isabel’s Bar, where a little thimble of lore pairs perfectly with a poolside cocktail. Find your spot in the sun, take a dip, and soak up a little Old Town intrigue.

Amenities at Lighthouse

From complimentary breakfast to bicycle rentals, convenient parking, and a concierge who knows the island, every detail makes exploring Key West feel effortless.

 

  • Welcome Cocktails

    A little nod to Isabel’s storied past, two signature thimbles await your arrival, each good for a welcome cocktail at our poolside bar.

  • Complimentary Breaekfast

    Complimentary continental breakfast is served poolside each morning from 8:00 AM to 10:00 AM. Guests may also enjoy a selection of chef-prepared à la carte breakfast specialties available for purchase.

     

  • Part of Your Stay

    The little extras make all the difference. Enjoy continental breakfast, fresh coffee and tea, complimentary Wi-Fi, filtered water, yoga mats, and a daily happy hour, all part of life at Lighthouse Hotel.

     

  • On-Site Bike Rentals

    See Key West your way with convenient on-site rentals from Island Safari Rentals, including cruiser bikes, e-bikes, scooters, and golf carts for every kind of island adventure.

  • Personalized Experiences

    From in-room surprises and celebratory bubbly to sunset sails and island adventures, let our concierge add a personal touch to your Key West stay.

Your People. Your Place.

Some occasions call for a little Key West character. Gather your favorite people for wedding weekends, family reunions, milestone birthdays, or a getaway just because. With Hemingway’s home across the street, cocktails at Isabel’s, and Duval Street around the corner, Lighthouse Hotel makes a memorable home base for your next group escape.

Around the Lighthouse: One Day Itinerary

Follow in Hemingway’s footsteps, wander the colorful streets of Old Town, and leave a little room for mischief. Curated by our Lighthouse Hotel innkeepers, this one-day itinerary brings together their favorite local haunts, literary landmarks, and after-dark adventures, all just steps from your door.

Stay inspired,
The lighthouse hotel Innkeepers
  • A Date with Hemingway

    9:30 AM

    Start across the street at the Ernest Hemingway Home & Museum. Meet the famous six-toed cats, wander the writer’s former home, and discover a few stories that never made it into his novels.

  • Take the High Road

    11:00 AM

    Climb the 88 steps of the Key West Lighthouse for sweeping island views and a little perspective on Old Town’s seafaring past.

  • A Little Lunch, A Little Lime

    12:30 PM

    Stroll over to Moondog Café, a colorful Old Town favorite, for a leisurely lunch and a slice of Key lime pie. Because no Key West afternoon is complete without a little something sweet.

  • Scandal on the Rocks

    3:30 PM

    Return to Lighthouse Hotel for a poolside cocktail at Isabel’s. Named for Hemingway’s seamstress and rumored mistress, it’s the perfect place to trade a little gossip of your own.

  • Duval After Dark

    8:00 PM

    Follow the music down Duval Street. Pop into a lively bar, order another round, and let the night write its own ending.

All That Glitters

They say every old Key West property has a secret, and Lighthouse Hotel is no exception. During renovations in the 1980s, more than two pounds of gold coins and nuggets were reportedly discovered in an old well on the grounds. Who left them behind, and why? No one seems to know. Just another golden chapter in Key West’s colorful past.

” The location of this hotel is absolutely perfect: just around the corner from Duval Street, yet wonderfully peaceful and quiet. ” -Trip advisor review

See What's Happening

There’s always something happening in Key West. Explore our calendar for live music and events at the inns, plus festivals, celebrations, and island favorites happening around town during your stay.

  • Oct25

    Live Music from Gi & Rolando

    Blending island-inspired melodies with acoustic favorites, their performances provide the perfect backdrop for a leisurely relaxing breakfast at Lighthouse.

    • Lighthouse Hotel
    • 9:00 AM to 11:00 AM
  • Oct13

    The Studios of Key West

    The Studios of Key West is a historic Old Town arts center offering sunset rooftop happy hours, rotating art exhibitions, performances, film screenings, workshops, and unique spaces for meetings and events bringing together local and visitors in an inspired island setting.

    • 10:00 AM to 4:00 PM
  • Rose at Ella's Cottage
    Oct11

    Paradise, Poured

    Join us each afternoon at Ella's Cottages for a complimentary glass of Roseblood Rosé, offered daily from 3:00 PM to 4:00 PM.

    • Ella’s Cottages
    • 3:00 PM to 4:00 PM
  • Oct11

    Cypress Sangria

    Gather at Ridley House each afternoon for a complimentary glass of our signature Cypress Sangria, thoughtfully crafted in-house and served daily from 3:00 PM to 4:00 PM.

    • Ridley House
    • 3:00 PM to 4:00 PM
  • bartender at winslows bungalow
    Oct11

    Bungalow Bar’s Daily Happy Hour

    Sip, relax and unwind with drink specials served daily at Bungalow Bar at Winslow’s Bungalows.

    Join us for an extended daily local favorite with half off select libations from 4 – 6 PM.

    • Winslow’s Bungalows
    • 4:00 PM to 6:00 PM
  • Oct11

    Sunset Celebration at Mallory Square

    A nightly festival and community tradition held right on the waterfront at Mallory Square. Every evening, locals and visitors gather to watch the sun sink into the Gulf of America while soaking up a lively arts-festival atmosphere.

    • 4:00 PM to 5:00 PM
  • Oct11

    Isabel’s Daily Happy Hour

    Sip, relax and unwind with drink specials served daily at Isabel's at The Lighthouse Hotel.

    Join us for an extended daily local favorite with half off select libations from 4 – 6 PM.

    • Lighthouse Hotel
    • 4:00 PM to 6:00 PM
  • Mojitio
    Oct12

    Rum, Lime, and Sunshine

    Kick off the week with a refreshing favorite. Every Monday from 2:00 PM to 4:00 PM, enjoy Buy One, Get One Margaritas and Mojitos at Isabel's Lighthouse and The Bungalow Bar.

    • Lighthouse Hotel, Winslow’s Bungalows
    • 2:00 PM to 4:00 PM
  • Tito's Drink Specials
    Oct13

    From Sunrise to Sunset

    Enjoy Tito's drink specials all day at The Bungalow Bar, located at Winslow's Bungalows. From your first afternoon cocktail to an evening nightcap, discover refreshing Tito's favorites served throughout the day in the heart of Old Town.

    • Winslow’s Bungalows
    • 11:00 AM to 8:00 PM
  • Oct14

    Live Music from Sam Carlson

    Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

    • Winslow’s Bungalows
    • 4:00 PM to 6:00 PM
  • Friends toasting, saying cheers holding summer cocktails.
    Oct14

    Wine Down Wednesday

    Midweek is the perfect time to slow the pace and enjoy a glass of wine in the heart of Old Town. Every Wednesday from 6:00 PM until close, join us at The Bungalow Bar for half off wines.

    • Winslow’s Bungalows
    • 4:00 PM to 8:00 PM
  • Oct15

    Throwback Thursday

    Raise a glass to the classics every Thursday at The Bungalow Bar. Enjoy $10 classic cocktails all day, featuring timeless favorites served in the relaxed setting of Winslow's Bungalows.

    • Winslow’s Bungalows
    • 11:00 AM to 8:00 PM
  • Oct15

    Truman Waterfront Park Thursday Market

    Key West Farmers Market brings local vendors together every Thursday from 1–6 PM at Truman Waterfront Park, featuring fresh produce, artisan foods, native plants, handmade goods, and local crafts. A perfect way to shop by the sea and experience the island community.

    • 1:00 PM to 6:00 PM
  • Oct15

    Live Music with Sam Carlson

    Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

    • Lighthouse Hotel
    • 4:00 PM to 6:00 PM
  • Oct15

    Live Music from Jamie Sellers

    Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

    • Winslow’s Bungalows
    • 4:00 PM to 6:00 PM
  • Oct16

    Flocktail Friday

    Think pink and join us for Flocktail Fridays at Isabel's Lighthouse. Wear your favorite pink attire, tag @KeyWestHistoricInns in your social post, and receive 10% off your bar tab from open to close.

    • Lighthouse Hotel
    • All Day
  • Oct16

    Fantasy Fest

    Celebrating all things fantastical, this legendary Key West party lasts for 10 days and dates back to 1979. This year's theme is Musical Icons & Iconic Musicals.

    • All Day
  • Oct16

    Live Music from Wavy Davy

    Spend the afternoon with live music from Wavy Davy at The Bungalow Bar at Winslow's Bungalows. Find a spot by the pool, enjoy a refreshing drink, and let the laid-back sounds of the island carry you through the day.

    • Winslow’s Bungalows
    • 4:00 PM to 6:00 PM
  • Oct16

    Live Music from Martin Sedlak

    Ease into the island’s rhythm with live jazz and folk music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

    • Lighthouse Hotel
    • 4:00 PM to 6:00 PM
  • Drums
    Oct17

    Live Music from Toko Irie

    Start your Saturday with the sounds of reggae as Toko Irie performs live at The Bungalow Bar. Known for his smooth rhythms and uplifting island sound, Toko Irie brings an authentic reggae performance to the heart of Old Town, creating the perfect backdrop for a leisurely morning.

    • Winslow’s Bungalows
    • 9:00 AM to 11:00 AM
  • Oct17

    Live Music with Nina Newton

    Enjoy an afternoon of live piano music with Nina Newton at Isabel's Bar.

    • Lighthouse Hotel
    • 2:00 PM to 4:00 PM
  • Goombay Festival
    Oct18

    Goombay Festival Key West

    Celebrate Key West’s Bahamian heritage with Caribbean music, Junkanoo traditions, island flavors, arts, and community spirit at the lively Goombay Festival in Bahama Village.

    • All Day
  • Oct18

    Live Music from Martin Sedlak

    Ease into the island’s rhythm with live jazz and folk music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

    • Winslow’s Bungalows
    • 9:00 AM to 11:00 AM
  • artisan market
    Oct18

    Key West Artisan Market: Fantasy Fest Edition

    Shop local art and handcrafted finds, enjoy food, drinks, and live music at the Key West Artisan Market’s Fantasy Fest edition near Higgs Beach.

    • 10:00 AM to 2:00 PM
  • Oct20

    Greatest Hits Pool Party

    Greatest Hits Pool Party takes center stage during Fantasy Fest at Winslow's Bungalows. Come dressed as your favorite music icon, sing your favorite hits during poolside karaoke, dance to live DJ sets, and compete for Best Dressed and Best Performance.

    • Winslow’s Bungalows
    • 12:00 PM to 4:00 PM
  • Oct23

    Live Music from Aaron Luka

    Kick off your Friday with live music from Aaron Luka at Isabel's Lighthouse. Blending acoustic favorites with an easygoing island style, Aaron's performances set the tone for a relaxed afternoon in the heart of Old Town.

    • Lighthouse Hotel
    • 4:00 PM to 6:00 PM
  • Oct28

    Trop Rock’N Duval – Mick Fury

    Kick off Trop Rock N' Duval with Mick Fury as he brings his signature blend of rock, blues, Americana, and island favorites to Winslow's Bungalows for an unforgettable afternoon of live music.

    • Winslow’s Bungalows
    • 12:00 PM to 4:00 PM
  • Oct29

    Trop Rock’N Duval -Reggie Starrett

    Spend the afternoon with Reggie Starrett as he brings a mix of acoustic favorites, easygoing melodies, and island-inspired sounds to Winslow's Bungalows during Trop Rock N' Duval.

    • Winslow’s Bungalows
    • 2:00 PM to 5:00 PM
  • Oct30

    Trop Rock’N Duval – Ricky Lamb

    Join Ricky Lamb for an afternoon of original music, classic hits from the '60s through the '90s, and the laid-back Trop Rock sound that captures the spirit of Key West.

    • Winslow’s Bungalows
    • 2:00 PM to 5:00 PM
  • Oct31

    Live Music from Wichita Jack

    Start your morning with live music from Wichita Jack at Isabel's Lighthouse. A solo musician based in Key West, Wichita Jack brings a laid-back blend of rock and roll inspired by artists including Eric Clapton, Tom Petty, Pink Floyd, Paul Simon, Jim Croce, Bob Dylan, and more.

    • Lighthouse Hotel
    • 9:00 AM to 11:00 AM
  • Oct31

    Live Music from Nina Newton

    Enjoy an afternoon of live piano music with Nina Newton at The Bungalow Bar at Winslow's Bungalows. Blending timeless melodies with contemporary favorites, Nina's performances create a relaxed backdrop for a leisurely afternoon in the heart of Old Town.

    • Winslow’s Bungalows
    • 2:00 PM to 4:00 PM
  • Oct31

    Trop Rock’N Duval – Dave Freeman & Friends

    Close out Trop Rock N' Duval with Dave Freeman & Friends as they perform a lively mix of original music, coastal favorites, and classic hits that capture the easygoing spirit of Key West.

    • Lighthouse Hotel
    • 4:00 PM to 7:00 PM
  • Drag queens at Lighthouse.
    Nov1

    Drag Me To Lighthouse

    Keep the party going after Mangoes Brunch 'Drag Royale' with Drag Me to the Lighthouse, a lively meet-the-queens afterparty at Isabel’s Bar from 3–5 PM.

    • Lighthouse Hotel
    • 3:00 PM to 5:00 PM
  • Nov1

    World’s Fastest Boat Parade

    The World's Fastest Boat Parade brings the excitement of offshore racing to the heart of Old Town as race teams and their powerboats make their way down Duval Street during the Race World Offshore Key West World Championships.

    • 4:00 PM to 5:00 PM
  • Nov2

    Race World Offshore World Championship

    The Race World Offshore Key West World Championship returns to Truman Waterfront Park, bringing the world's fastest offshore powerboats to the waters surrounding Key West for the final race of the national series.

    • All Day
  • Dec12

    Lighted Boat Parade

    Celebrate the season as beautifully decorated boats illuminate the Historic Seaport during one of Key West's favorite holiday traditions.

    • All Five Inns, Ella’s Cottages, Fitch Lodge, Lighthouse Hotel, Ridley House, Winslow’s Bungalows
    • 6:00 PM to 12:00 AM
  • Literary Seminar
    Jan7

    Key West Literary Seminar

    Celebrate Key West’s literary legacy with acclaimed authors, engaging conversations, readings, and writers’ workshops at the annual Key West Literary Seminar.

    • All Day
  • Jan15

    29th Annual Key West Half Marathon & Runfest

    Trade winter for sunshine and ocean views at the 2027 Key West Half Marathon & Runfest, featuring four races and a full weekend of island celebrations.

    • All Day
  • Jan26

    Mile 0 Fest Key West

    Five days of Red Dirt, Americana, sunshine, and island energy come together for Mile 0 Fest Key West, celebrating its 10th anniversary in 2027.

    • All Day
  • Jan27

    Key West Food & Wine Festival 2027

    Five continents, incredible wines, celebrated chefs, and global flavors come together for five unforgettable days at the 2027 Key West Food & Wine Festival.

    • All Day
  • Seafood Festival
    Feb13

    Florida Keys Seafood Festival

    Taste the Florida Keys at this waterfront celebration of fresh local seafood, live music, island culture, and the community behind the catch.

    • All Day
  • Conch Republic
    Apr16

    Conch Republic Independence Celebration

    Declare your FUN-dependence during 10 days of parades, pirates, live music, waterfront celebrations, and wonderfully Key West traditions.

    • All Day

22&Co

This vibrant, inclusive and creative bar offers tons of local charm to go along with happy hours, fresh cocktails, fun bartenders and weekly drag shows.

801 Bourbon Bar

Head to this lively LGBTQ+ venue on Duval Street for its energetic atmosphere, entertaining drag shows and diverse cocktail offerings.

Alan S. Maltz Gallery

Immerse yourself in Key West’s vibrant entertainment scene at the newly renovated Key West Theater, just a 3-minute stroll from Ridley House, offering the best in comedy, concerts, and live performances.

Aqua Bar and Nightclub

Known for its energetic drag shows, inventive cocktails and upbeat atmosphere, Aqua Bar is a popular destination for those seeking a memorable night out in Key West.

B.O.’s Fish Wagon

Offbeat, eclectic and undeniably delicious. B.O.’s Fish Wagon, just a 3-minute walk from Ridley House, delivers big on fresh flavor and Key West vibes.

Bagatelle

Fresh local seafood and creative cuisine are the stars at this elegant restaurant. Housed in a gorgeous and historic Duval St. location.

Bahama Village Shopping

Explore this diverse array of shops, boutiques, and galleries that showcase local art, crafts, and unique souvenirs in a charming and culturally rich neighborhood.

Better Than Sex

Stroll over to Better Than Sex, an intimate dessert restaurant offering a speakeasy-like atmosphere and tempting sweets and cocktails.

Blue Heaven 

An eclectic menu, vibrant atmosphere and live music combine to create a unique and unforgettable dining experience at this restaurant nestled in a tropical garden.

Boat House Bar & Grill

Voted “Best Happy Hour in Key West,” this fun and friendly harborfront restaurant is the perfect place to eat and drink local favorites with an unbeatable view.

City of Key West Old Town Garage

Coffee Butler Amphitheater

Surrounded by tropical beauty, this amphitheater provides a vibrant setting to enjoy concerts, festivals and other entertainment experiences in the heart of Key West.

Danger Charters

Sail into the breathtaking beauty of the Florida Keys on unforgettable schooners designed to reveal both must-see landmarks and hidden gems.

Dante’s Pool Bar & Restaurant

Make a splash and enjoy the bustling atmosphere of Dante’s, an oasis of good times that combines sun, swimming, dancing, and all-day revelry. Perfect for bachelor, bachelorette and birthday parties.

Date & Thyme Organic Cafe & Market

Visit Key West’s best natural food market and the largest purveyor of organic and local produce. The cafe offers a menu of healthy smoothies and juices along with hearty breakfast and lunch favorites.

Ellas Lobby

Ella’s Cottages

811 Simonton Street

Sit back and watch the world go by, just steps from some of the city’s best dining experiences. These charming bungalows exude the romance and carefree spirit of Key West.

Pool

Fitch Lodge

The ideal Key West basecamp for on-the-go explorers, island-hoppers and open-water adventurers. A neighborhood vibe welcomes you to go your own way in Key West.

Fury Water Adventures

For the ultimate water adventure, explore a wide range of watersports with Fury Water Adventures, your go-to source for sunset cruises, jet ski excursions, and more in Key West.

Green Parrot Bar

This legendary Key West watering hole is celebrated for its lively atmosphere and iconic live music. Residents and visitors are welcomed with vibrant energy and diverse entertainment offerings.

Greene Street Cigar Company

Immerse yourself in a world of premium cigars and a diverse menu of craft beer and wine, just a 2-minute walk from Ridley House. The walk-in humidor boasts Key West’s largest cigar selection.

Half Shell Raw Bar

Sample the freshest oysters, clams, shrimp and more at this scenic and friendly Key West institution that has been welcoming seafood lovers since 1972.

Kermit's Key West Lime Shoppe

Bright and colorful, with a diverse selection of treats that will keep you coming back again and again. Kermit has been serving sweets for over 30 years. Just four minutes from Ridley House.

Key West Cemetery

Established in 1847, this cemetery reflects Key West’s diverse cultural history. It’s a fascinating destination for visitors interested in exploring the eclectic charm of Key West.

Key West First Legal Rum Distillery

Discover the secrets behind Key West’s favorite spirit by embarking on a free distillery tour, a quick 4-minute walk from Ridley House. Savor free samples, relax at the bar, or purchase bottles to take home.

Key West Lighthouse

You can’t miss it! The Key West Lighthouse and Keeper’s Quarters are just 200 feet away from Lighthouse Hotel, offering an iconic backdrop for your Key West getaway.

Key West Pottery

Visit this unique studio known for its distinctive handcrafted ceramics that showcase a blend of artistic expression and functional design, all inspired by the vibrant spirit of Key West.

Key West Theater

Immerse yourself in Key West’s vibrant entertainment scene at the newly renovated Key West Theater, just a 3-minute stroll from Ridley House, offering the best in comedy, concerts, and live performances.

La Crêperie 

This charming eatery specializes in French-style crepes served in a variety of sweet and savory options. It’s a favorite spot for anyone seeking a taste of authentic and delicious flavor.

Laid Back Key West

Welcome to Laid Back Key West! Looking for fun and adventure? Then it’s time to get out on the water. For over a decade, we have provided the best private charter boat tours in Key West. We want to take you, your family, and a few friends out on the spectacular warm turquoise waters of the Florida Keys.

Lighthouse Exterior

Lighthouse Hotel

Colorful, energetic and welcoming, with the very best views of Key West’s famous lighthouse. Centrally located, a stone’s throw from Ernest Hemingway’s House. Afternoon daiquiris are calling.

Little Pearl

Taste the best of the local catch at Little Pearl Fish House & Wine Bar, a creative neighborhood dining destination on Olivia Street in the heart of Old Town.

Lola’s Bistro

Discover a charming eatery celebrated for its eclectic and inventive cuisine, offering a delightful fusion of global flavors and a welcoming ambiance.

Mangia Mangia Pasta Cafe

If you love homemade pasta and Italian specialties, you won’t want to miss this local favorite restaurant on Southard Street in the heart of Old Town Key West.

Moondog Café

If fresh baked goods, hearty meals and anytime beverages are your thing, grab a seat on the colorful patio of Moondog Cafe & Bakery. Just a 1-minute walk from Lighthouse Hotel.

Nine One Five Restaurant & Bar

Set in a beautifully restored 19th-century building on Duval Street, Nine One Five offers a sophisticated dining experience with a diverse menu featuring contemporary American cuisine, craft cocktails and an inviting atmosphere.

Old Town Bakery 

Take a 2-minute stroll to Old Town Bakery to discover a diverse menu of pastries, sandwiches, and a key lime pie that was voted one of the best in the Florida Keys.

Onlywood Grill

Savor authentic Italian cuisine including homemade pastas, woodfire oven-baked pizzas, and tantalizing meats from an Argentinian grill.

OurKeyWest Galleria

From colorful Cuban art to the best of local makers, OurKeyWest Boutique offers a one-of-a-kind selection of gifts and handcrafts. A quick stroll up Simonton Street.

Papa’s Pilar Rum Distillery

For a refreshing taste of Key West’s rum culture, indulge in ice-cold cocktails at Papa’s Pilar Rum Distillery. A must see in Old Town, providing tours, tastings, and a journey into the art of rum-making.

Parking at Ella's Cottages

Limited on-site parking is available and can be inquired about at check in. $30 per night. Parking lot is located adjacent to Ella’s via Petronia St.

Parking at Fitch Lodge

No onsite parking available. Street and city lot parking available nearby.

Parking at Ridley House

No onsite parking available. Street and city lot parking available nearby.

Parking at Winslow's Bungalows

Limited on-site parking is available and can be inquired about at check in. $30 per night.

Pepe's Cafe & Steakhouse

A Key West classic, Pepe’s prides itself on being the “Oldest Eating House in the Keys”. Since 1909, it’s been serving up fresh local flavor and friendly vibes.

Ridley Second House Patio with chairs

Ridley House

601 Caroline Street

Escape to the bohemian luxury of our elegant, adult-exclusive tropical mansion. Discover Old Town’s most romantic inn, around the corner from Key West Historic Seaport.

Santiago’s Bodega

Visit this tapas-style restaurant for an eclectic menu featuring a variety of shareable plates and sangria. Known for its lively atmosphere, extensive wine list, and diverse range of flavors.

Sarabeth's in Key West 

Since 1981, Sarabeth’s has been serving up some of Key West’s favorite fare. Take a 4-minute stroll up Simonton Street and bring your appetite.

Seven Fish

Seafood lovers won’t want to miss a stop at Seven Fish, a casual bistro with dishes that feature the best of the local catch along with a menu of classic desserts and a deep wine list.

Sinz Burritos Key West

Savor the must-try street tacos, burritos, and quesadillas of Sinz Burritos on a short 5-minute stroll down Truman Street, where you can build your own or enjoy their unique takes on classics.

Splash Pad at Truman Waterfront Park

The perfect spot for kids to expend their energy and stay cool under the Key West sun, this lively splash pad offers refreshing and entertaining water experiences.

Sunset Sail Key West 

Hit the water on a gorgeous fleet of schooners, including When and If—built in 1939 for General George S. Patton.

The Basilica of St. Mary Star of the Sea

Visit this historic Catholic church for its stunning architecture and rich history. Completed in 1905, the basilica is a popular site for visitors interested in Key West’s religious and architectural heritage.

The Green Pineapple 

Shop this charming boutique for a curated selection of eco-friendly products and unique gifts. A cozy café, offers healthy bites, coffee, tea and organic wine.

The Hemingway Home and Museum 

The spirit of one of Key West’s most iconic residents lives on. Tour the Hemingway Home & Museum, located right across the street from the Lighthouse Hotel.

The Key West Butterfly & Nature Conservatory

Step into a spectacular indoor environment featuring living butterflies and many colorful birds. This family-friendly sanctuary is a tropical paradise of waterfalls and plant life, with a gift shop offering unique souvenirs.

The Original Key West Ghost Hunt

Embark on a thrilling exploration of Key West’s ghostly past with The Original Key West Ghost Hunt.

The Waterfront Brewery

Combine scenic views with craft beer and island favorites at a picturesque local brewery, creating the perfect atmosphere for carefree Key West relaxation.

Vignette Key West

A boutique style destination in the heart of Key West for women who have their own story to tell. Take a 5-minute walk to Southard Street.

Vinos

Known for its extensive wine selection and Mediterranean-inspired menu, Vinos provides a delightful dining experience with a focus on pairing excellent wines with delicious dishes

ViV Wine Bistro

Authentic French fare combines with a sophisticated dining experience and an extensive selection of wines in a charming and cozy atmosphere. Bon appétit!

Winslow front Exterior

Winslow’s Bungalows

Play together among an eclectic collection of distinctly Key West structures. This lush green property invites every kind of carefree getaway, from family trips to wedding parties.

 

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