7 Unique Things to Do in Key West

Beyond the famous Duval Street and Ernest Hemingway Home, Key West offers a wealth of unique experiences. Rent Key West Vacations invites you to venture off the beaten path and discover all the unique things to do in Key West. From haunted history tours to hidden gem restaurants and one-of-a-kind neighborhoods, our island has something to pique everyone’s curiosity. Head to Key West and discover the quirky island of the Florida Keys: 

  1. Stop at the Hellings Curry Museum for a free tour and explore one of the few brick structures on the island. Stroll through the building and learn about the history of this 19th-century mansion. 
  2. Pay a visit to Nancy Forester’s Secret Garden and visit the orphaned parrots at this educational sanctuary. Learn about Nancy’s mission to rescue, rehome, and train these parrots during your visit, and stop in for storytime from 10-11 daily. 
  3. Wander the streets of historic Old Town with Ghost & Gravestones and learn the haunted history of Key West. Follow your Ghost Host as you hear tales of murder, disease, and misfortune.
  4. Stroll the unique and intriguing Key West Cemetery and use this map to learn about the island’s diverse heritage. Join the Historic Florida Keys Foundation walking tours twice a week.
  5. Experience the Key’s Caribbean heritage at the historic Bahama Village Neighborhood. Stroll the streets and admire the Bahamian architecture, visit the Village Market for souvenirs, and stop for tapas at Santiago’s Bodega.
  6. Learn all about Key West history at our newest museum: Sails to Rails Museum. Visit Key West Bight and stroll through exhibits featuring raw footage, unique artifacts, and a scale model of Fort Jefferson.
  7. Discover the natural beauty of Key West on a Fury Cat Eco Tour. Board a catamaran and head to a backcountry sandbar for snorkeling, kayaking, watching wildlife, and relaxing.

Hidden Gem Restaurants in Key West

If you are looking for some delicious food off the beaten path, we have you covered. Stop at Garbo’s Grill at Hank’s Hair of the Dog Saloon for seasonal specialties like New England lobster rolls and poke bowls. And if you are looking for bars off the beaten path, we recommend going to Berlin’s behind A&B Lobster House. Settle into a cozy leather chair, order a drink from the speakeasy-style cocktail bar, and listen to jazz music as you sip on your cocktail. 

Book Unique Lodging in Key West with RKW

Skip the hustle and bustle and check out all the unique things to do in Key West during your getaway with Rent Key West Vacations. Find unique lodging, like our 1840’s 11-bedroom Watson House Grand Estate, and stay in a piece of Key West history. Whether you want to stay in the historic district or near the beach, we have the perfect Key West vacation rental for your Florida getaway!

Where to Attend a Drag Show in Key West

As an internationally known LGBTQ+ travel destination, Key West Florida is celebrated for its inclusivity and openness. Among its many treasures, Key West boasts a dazzling drag show scene that is not to be missed. Attend a drag show in Key West and experience a night of comedy, glamour, costumes, entertainment, and laughter at Aquaplex, 801 Bourbon Bar, Mangoes, or La Te Da. Come as you are in and stay with Rent Key West Vacations, a proud Key West Business Guild member, a nonprofit organization promoting LGBTQ+ travel in the Keys!

Aquaplex Key West

Aquaplex offers drag shows every night in Key West! Attend a show at Aqua Bar and Night Club and witness the Aquanette’s showstopping drag performance. Aquaplex is also home to the island’s newest live act, The Birdcage Cabaret. See drag icon Christopher Peterson take the stage and show off impersonations while singing and lipsyncing with various local performers, female singers, and jugglers. 

801 Bourbon Bar

Visit 801 Bourbon Bar and attend the longest-running drag show in Key West at 9 pm or 11 pm nightly. Meet the 801 Girls and expect a night of beauty and comedy with a variety of talented entertainers!


Mangoes hosts a special Sunday Drunken Drag Brunch once a month that is not to be missed. Plan your getaway around one of these fabulous brunches and experience Drag Queen performances, a live DJ, bottomless mimosas, specialty cocktails, and a la carte brunch food. Purchase tickets for upcoming events and proceeds will be donated to local charities. 

La Te Da

Make your way to the La Te Da hotel and attend the Randy Roberts Live Cabaret show during your time in Key West. With over three decades of experience, Randy Roberts presents a classic drag show with live vocals, stunning costumes, and impersonations. Purchase tickets to the Tuesday, Friday, Saturday, or Sunday shows starting at 8 pm!

Welcoming Everyone to Our Key West Vacation Rentals 

Check out the bustling nightlife scene during your visit and purchase tickets to one of the drag shows in Key West. Book your getaway with Rent Key West Vacations and find the perfect Key West vacation rental for your unique needs. For assistance customizing your Key West vacation, please contact us at 1-800-833-7368. 

The Best Bars in Key West to Visit on Vacation

Key West is famous for its sunsets, turquoise waters, white sand beaches, rich history, and lively nightlife. Escape to the southernmost point in the U.S. with Rent Key West Vacations and check out the island’s top attractions during your visit. Make your way to Duvall Street and discover the best bars in Key West, offering refreshing cocktails, live music, happy hours, and local history. Whether you want to grab a drink at Ernest Hemingway’s favorite watering hole or catch the sunset at a bar along Mallory Square, there is a destination for everyone:

Sloppy Joe’s

Visiting the historic Sloppy Joe’s is a must during your Key West vacation. This bar has been a Key West tradition since 1933 and is famous for being Ernest Hemingway’s favorite watering hole. Hang out in a piece of Key West history and grab a drink at Joe’s Tap Room, serving craft beer and tasty cocktails. Joe’s also offers one of the best parties in town, with live music daily from noon to 2 a.m.

Green Parrot Bar

Another Key West icon, the building of the Green Parrot Bar, started as a grocery store in the 1890s, turned into a dive bar after WWII, and was renovated in the 1970s as the Green Parrot Bar. Today, the bar is a favorite destination for live music on the island, with live local musicians taking the stage multiple times daily.

Irish Kevin’s

Visit Irish Kevin’s on Duval Street for a classic Irish pub experience in the Keys. Enjoy unique cocktails like the world-famous Green Gator, featuring lemon rum, blue curacao, oj, sour mix, and 151 floaters in a souvenir glass. Stop in for live music, drinks, burgers, sandwiches, and delicious Key Lime pie!

Captain Tony’s Saloon

Captain Tony’s Saloon was the original location of Sloppy Joe’s Bar, located directly across the street. This historic saloon was the favorite watering hole for celebrities like Ernest Hemingway, Truman Capote, Tennessee Williams, and Jimmy Buffet. Unique pieces of Key West history are found all over the bar, including the stools painted with famous visitors’ names.

Sunset Pier

If you are looking for a Key West bar to watch the sunset over the water, we recommend visiting Sunset Pier near Mallory Square. Enjoy live music, tropical drinks, breathtaking sunset views, and delicious seafood. 

Key West Vacation Rentals near Duval Street

Book your getaway with Rent Key West Vacations and stay close to the action with our vacation rentals in Old Town. Properties like Ann Street Cottage, Tranquility, and Namaste put you minutes away from the best bars in Key West. Stay within one block of Duval Street and two blocks from famous bars like Sloppy Joe’s, The Bull, and Hog’s Breath. To customize your vacation, please call our reservation specialists at 1-800-833-7368. 

Indulge in Key West Spa Treatments on Vacation

After a day of exploring Key West’s beaches, museums, and historic sites, unwind at one of our local spas. Experience the ultimate relaxation at our Key West spas, which feature healing massages, facials, and body wraps. Or utilize mobile massage services to bring healing to the comfort of your Rent Key West rental home! However you want to focus on your wellness, Key West offers the perfect setting for rest and rejuvenation in the Sunshine State:

Ocean Wellness Spa and Salon

Sign up for massages, facials, and body treatments at Ocean Wellness Spa and Salon in the heart of Old Town Key West. Feel your aches and pains melt away with a wide variety of regenerative massage therapy treatments, or look your best on vacation with a visit to the salon!

Amri Day Spa

Amri Day Spa is an ethical and sustainable day spa that puts people and the planet above everything else. Everything in the spa is ethically made, and 95% of waste is recycled. Sign up for massages and facials that are good for you and the planet at this Key West spa!

Prana Spa

Heal your mind, body, and soul at Prana Spa in Old Town. Your healing begins from the moment you enter the building, where you are greeted by the scents of sandalwood and lemongrass and the sounds of meditational music. Then, choose from massages, skincare treatments, or experiences that combine healing for both the body and soul!

Flow Spa Key West

Head to Flow Spa Key West and look and feel your best on vacation! Start with a healing Swedish, Therapeutic, Hot Stone, Deep tissue massage. Then, indulge in a salon treatment like eyebrow tinting, eyelash extensions, waxing, manicures, or pedicures. 

SpaTerre Key West

SpaTerre is located within Ocean Key Resort, offering several services for day guests. Choose from their menu of facials, massages, or body wraps. Enjoy access to the fitness center on the day of your treatment, which offers ellipticals, treadmills, dumbells, a patio stretching area, and more.

Essera Spa

Essera Spa offers mobile massage services in Key West. Reserve a massage appointment in your Key West vacation rental and experience healing without leaving the property. Please contact 305-783-8550 to book your massage!

Key West Vacation Rentals for Your Wellness Retreat

Whether you want to spend the day at a Key West spa or bring the massage to you, we offer healing services for everyone on the island! Book your stay with Rent Key West Vacations and find the perfect vacation rental for your Florida getaway. We offer over 60 Key West vacation rentals ranging from studio apartments to multi-family estates. Please call our reservation specialist at 800-833-7368 to learn more about booking your Key West vacation!

Discover the Key West Shopping Scene on Vacation

Discover the Key West shopping scene on vacation and find the perfect souvenir to remember your time in the Florida Keys! From charming boutiques selling trendy fashion items to art galleries showcasing original art, there is a shop for every interest. Stay with Rent Key West Vacations and easily access the shops along Duval Street near your vacation rental. Here are seven unique shops to check out during your visit:

1. Key West Aloe

Key West Aloe has been an island staple for over 50 years. They use lab-certified aloe to formulate a wealth of fantastic aloe products. Stop in at the store on Greene Street to shop for sun care, skincare, body care, hair care, and fragrances. 

2. Mallory Square Shops

Explore Duval Street and Mallory Square for the best Key West shopping experience. We recommend the Southernmost Point Gift Shop, The Green Pineapple Boutique, and Tucker’s Provisions along Duval Street. Then, walk down to the Mallory Square Shops and visit charming boutiques, art galleries, and more!

3. Besame Mucho

Stop at Besame Mucho in the Bahama Village area and shop for a wide selection of apothecary, jewelry, home decor, confections, paper, tools, and souvenirs.

4. Key West Sponge Market

Buy a natural sponge harvested in Florida at the Key West Sponge Market! Sea sponges are a great eco-friendly alternative to other sponge options. 

5. Kermit’s Key Lime Shop

No visit to Key West is complete without stopping at Kermit’s Key Lime Shop! Browse a wide variety of key lime treats like pie, juice, cookies, candy, sauces, salsa, relish, specialty oils, jams, and jellies. 

6. Key West Butterfly & Nature Conservatory

After exploring the Key West Butterfly & Nature Conservatory, head to the gift shop for some fantastic souvenir shopping! Shop for butterfly-themed artwork, books, apparel, accessories, toys, home decor, jewelry, and souvenirs.

7. Key West Art Galleries

Find the perfect piece of original art at one of our Key West art galleries. Stop at Sacred Space Gallery for unique gifts and artwork made exclusively by women who call the Florida Keys home! Then, visit the Key West Art Center and browse their sculptures, paintings, and ceramics selection from over 50 local artists.

Book Your Key West Getaway Today!

Explore the Key West shopping scene on vacation and bring a piece of Florida home with you! Choose Rent Key West Vacations to host your getaway and discover the charming shops near your Key West vacation rental. Whether you want to stay near the beach or in the historic district, we have the perfect property waiting for you. To customize your Key West vacation, please contact us at 1-800-833-7368.