Plan a Key West Romantic Getaway

Nestled at the southernmost tip of the United States, Key West offers the perfect setting for romance. Let Rent Key West Vacations help you craft the perfect stay with our fabulous vacation rentals for couples, concierge services, and knowledgeable staff. Whether you are interested in sailing our waters on a sunset cruise or enjoying a meal from the comfort of your vacation home, there are endless ways to celebrate your love with a Key West romantic getaway!

Enhance Your Stay with Rent Key West Vacations

Make the most of your Key West romantic getaway, and let our concierge help arrange amenities and activities to enhance your stay. Our professional concierge is available seven days a week to help plan your vacation. Don’t hesitate to get in touch with us at!

  • In-Home Chefs: Enjoy fresh, locally sourced cuisine prepared by a talented chef from the comfort of your vacation rental!
  • Gift Baskets & Specialty Services: Arrive to a gourmet gift basket in your vacation rental with local snacks, sweets, and spirits.
  • Floral arrangements: Fill your vacation rental with the scents and sights of a beautiful tropical flower arrangement.
  • Tours: Book tours and activities from our website, like snorkeling, scuba, sunset sails, and eco-tours.

3 Things to Do During Your Key West Romantic Getaway

1. Spend Time at the Beach

Spend time together at our beautiful Key West beaches like Smathers Beach or Fort Zachary Taylor Historic State Park. Whether you want to explore the water, stroll hand in hand at sunset, or set up a beach picnic, our beaches offer the perfect setting for romance!

2. Embark on a Romantic Sunset Cruise

Sign up for a romantic sunset cruise on Key West! Danger Charters offers a special Wind & Wine Sunset Sail aboard a classic schooner for a relaxing and romantic tour. Discover even more romantic sunset tours with Sebago Watersports or Catarman Echo

3. Enjoy a Romantic Key West Dinner

Several romantic restaurants in Key West offer the perfect date night spot. Enjoy elegant beachfront dining at Latitude’s, one of the top eateries in the Florida Keys! Other romantic restaurants include Hot Tin Roof, Louie’s Backyard, and Prime Steakhouse.  

Book Our Key West Vacation Rentals for Couples

Book your Key West romantic getaway with Rent Key West Vacations today! Browse our Key West vacation rentals for couples and find the perfect property for you and your special someone. Whether you are looking for a private cottage or a waterfront condo, we have something for everyone. Your romantic adventure awaits in the Florida Keys!

Your Guide to Key West Public Beaches

No visit to Key West is complete without spending time splashing and suntanning at our beautiful Key West public beaches! Stay with Rent Key West Vacations in our oceanfront condos and access our white sand beaches just steps from your rental property. Soak up the Florida sunshine as you swim, sunbathe, snorkel, and paddle at our fantastic beaches. From the tranquil shores of Smathers Beach to historic Higgs Beach, there is a beach for everyone in our tropical paradise! 

Smathers Beach

Smathers Beach is the largest of the Key West public beaches, welcoming over 150,000 people annually! This beach is a half-mile long and is located on the south end of the island, offering access to several amenities such as:

  • Beach volleyball nets and volleyball courts
  • Restrooms
  • Shower Facilities
  • Access to tours and water activities with Sunset Watersports

Clarence S. Higgs Memorial Beach

Clarence S. Higgs Memorial Beach offers almost 17 acres of beachfront along the Atlantic Ocean. This beach is the best option for travelers who want easy access to a wealth of amenities and attractions. Higgs Beach offers direct access to the Key West Marine Park, one of the best snorkeling areas on the island! Make sure to take advantage of the beach amenities such as:

  • Children’s playgrounds
  • Picnic tables
  • Restroom facilities
  • Tennis and volleyball courts
  • Concession stands
  • Tiki huts
  • Wooden grandstand
  • Wooden pier

Simonton Street Beach

Simonton Street Beach is the perfect option if you are looking for a small beach on the Gulf side of the island! The only amenities on the beach are restrooms and a boat ramp for recreational boats. Make sure to bring beach gear with you!

Dog Beach

If you are traveling to Key West with your four-legged friends, we recommend visiting Dog Beach. Stay in our pet-friendly vacation rentals in Key West and access the only dog-friendly beach nearby!

South Beach

If you are staying on Duval Street, we recommend visiting South Beach, on the southern end of Duval Street. This small beach is an excellent place to watch the sunrise or sunset!

Bonus: Fort Zachary Taylor Historic State Park

Although not a public beach, Fort Zachary Taylor Historic State Park is considered one of the best Key West beaches! Find everything you need for a day at the beach with Chickee Hut Beach Rentals, offering umbrellas, lounge chairs, and snorkeling gear. Then, enjoy beach activities like swimming, snorkeling, fishing, paddling, scuba diving, and suntanning.

Book Key West Beachfront Vacation Rentals

Spend time in Florida’s southernmost city with Rent Key West Vacations, and spend your getaway exploring our beautiful Key West public beaches. Browse our collection of over 30 Key West vacation rentals near the beach and enjoy access to our beaches just steps from your rental home! Enhance your stay with our concierge services and let our team make your vacation even more enjoyable. 

Book your Key West beach vacation today, and don’t hesitate to contact us with any questions!

Free Things to Do in Key West

Your Florida vacation doesn’t have to break the bank; save on your upcoming getaway with Rent Key West Vacations! Take advantage of all the free things to do in Key West, from strolling down iconic Duval Street to soaking up the sun at our beautiful beaches. In addition to free activities on the island, many of our vacation rentals are part of larger condominiums so that you can enjoy elevated amenities like swimming pools, tennis courts, and fitness centers. Pack your bags, leave your worries behind, and get ready to discover a budget-friendly vacation in Key West!

Discover Free Things to Do on Duval Street

Duval Street runs the entire distance of the island and offers a plethora of free activities: 

  • Start at the South End of Duval Street and take a picture together at the Southernmost Point
  • Use the free self-guided walking tour to learn about all the notable attractions on Duval Street. 
  • End your day at Mallory Square and join the free Sunset Celebration, full of entertainment, live music, and food vendors.  

Free Activities at Key West Beaches

Spend a day at the public beaches in Key West and enjoy free activities the whole family will enjoy:

  • Visit Smathers Beach, offering a half mile of soft sand with amenities like beach volleyball nets, restrooms, and shower facilities. 
  • Visit Clarence S. Higgs Memorial Beach Park and enjoy swimming, snorkeling, sunbathing, beach volleyball, tennis, pickleball, and children’s playgrounds. 
  • Head across the street from Memorial Beach and visit the Key West Garden Club at West Martello. Explore a former Civil War fort and several gardens home to an impressive collection of rare and exotic plants!

More Free Things to Do in Key West

Looking for more free things to do in Key West? Here are a few more activities found throughout the island:

Key West Vacation Rentals for Every Budget

Book your getaway with Rent Key West Vacations and enjoy all the free things to do in Key West near your rental home. Browse our collection of Key West vacation rentals and find the perfect property for your group. Please contact our reservations specialist at 1-800-833-7368 to customize your Key West getaway today!

Your Guide to Old Town Key West

Key West may be known for its stunning white sand beaches, but the Southernmost Point is also home to a rich and fascinating history. Step back in time in the neighborhood of Old Town Key West and discover the island’s architectural heritage, fascinating history, and renowned museums. Choose Rent Key West Vacations to host your getaway and stay in the heart of Old Town with our historic vacation rentals!

Discover the History of Old Town

Discover all the attractions in Old Town Key West with Old Town Trolley Tours, offering hop-on and off sightseeing tours! Or use this self-guided walking tour to discover the best of Old Town on your own! 

  • Start your journey back in time at the Key West Lighthouse, an iconic landmark that has stood for over 150 years! Ascend the lighthouse and marvel at the artifacts that give insight into our maritime history. 
  • Discover the world’s largest cache of Civil War armament at Fort Zachary Taylor Historic State Park. This historic fort also offers recreational opportunities like bicycling, fishing, hiking, paddling, and snorkeling.
  • Located in the heart of Old Town, Duval Street is a fantastic gateway to local history. Discover the island’s most famous shops, restaurants, and nightlife spots here, including Sloppy Joes!
  • Discover the homes of Key West’s most famous residents at the Hemingway Home & Museum and the Truman Little White House Museum!

Don’t Miss the Top Attractions in the Historic District

No visit to Key West would be complete without snapping a picture at the Southernmost Point Buoy! You can find some of Key West’s top attractions just a block from the buoy, such as the Key West Butterfly and Nature Conservatory. Further down the road, you can visit the Key West Aquarium to learn about local marine life!

Stick Around for Nightlife on Duval Street

End your day in Old Town Key West with some fun at Mallory Square! Join the nightly Sunset Celebration here and enjoy local musicians, comedy shows, artists, entertainment, and food vendors. Or return to Duval Street at night for the best nightlife on the island. Visit iconic bars like Sloppy Joes and Green Parrot Bar!

Stay in Our Old Town Key West Vacation Rentals

Rent Key West Vacations offers fantastic vacation rentals in Old Town Key West to host your getaway! Discover our collection of over 40 properties, all with their own distinct architecture and history. From the charming one-bedroom Portside Suite to the eleven-bedroom Watson House Grand Estate, we offer something for everyone! 

Key West Offers Treasure Trove of Original Art

Key West is known for its extremely vibrant arts scene. The island has been attracting artists inspired by its natural beauty, rich history, and diverse culture. Today there are dozens of Key West galleries and museums for visitors to discover, offering a vast variety of art mediums and styles from local and international artists. This week we are featuring a few of our very talented local friends! You can bring home an original piece of art or some unique hand-crafted gifts keeping a piece of paradise in your home, sharing Key West culture with others, and always keeping our unique island in your heart!

Sacred Space Key West

PHOTO: Sacred Space Key West

Barbara Sage & Lucy Hawk founded Sacred Space Gallery in August 2020. They needed an art studio and quickly realized there was room to feature artwork by others as well. They continue to seek out other local women who create unique artwork & gifts. 

They proudly highlight 25 female artists and have four working studios. They offer a variety of art classes including painting, sculpting, and many unique Keys Coastal Classes; such as:  ‘Broken But Beautiful” Seaglass Class. Participants create an original piece of seaglass art. Seaglass, pottery, shells, driftwood bits and all necessities are all provided along with detailed instruction. Everyone leaves with a one-of-a-kind framed piece.

Their carefully curated gallery offers a sense of wonder and whimsy and the magic can be found in the heart of Old Town Key West at 529 Southard Street, between Simonton & Duval Streets. They are also available by phone, 305 998-4801 and via their website.

Key West Pottery

PHOTO: Konk Life

Artists Kelly Lever and Adam Russell began their collaboration in 2009. They blend traditional production pottery (tableware and functional vessels) with their fine art pieces.  

Since its inception, they have grown their company to include multiple artisans, creatives, students and collaborators. The talented group works together to produce a modern expression of coastal life while always being authentic and not relying on cliché.

Over the years they have developed a brand of tropical modernism that is unique and diverse so it can fit into any home or collection. In addition to commissioned, bespoke pieces, they carry everything from the island’s best coffee mugs to award winning totems. Their distinctive gallery with its well-rounded program is located on iconic Duval Street at number 1203. You can also reach them by phone, 305-900-8303, and online.

Key West Collective Art Gallery


This beautifully curated local art gallery is filled with a collective of talented artists inspired by Key West. Photographer and founder, Rachel E. Ligon, a native Kentuckian, has made Key West her home for more than 20 years. 

Ligon has traveled the world capturing diverse environments and the faces living there. Ligon’s passion recently led to her opening the Key West Collective Art Gallery on Caroline Street.  

In addition to her photography, the critically curated collective features the work of some of the island’s best artists, artisans and authors. The Collective also offers regularly scheduled classes where people can gather techniques from the featured artists. The Gallery at 720 Caroline Street is open daily 10am to 5pm and can be reached by calling 305-395-1161. The artists and their works can also be seen on the Collective’s internet site.

Key West Art Center

In the mid-1930s the Great Depression had devastated the nation including the Florida Keys. The federal Works Progress Administration brought artists and writers to Key West to help revitalize the economy. Many art classes were taught at the Key West Community Art Center, believed to be the WPA’s first public art project, which eventually became the Key West Art Center. 

The Center’s HQ since 1960 is pictured above and the organization is the steward of their home in this historic wooden building dating back to the 1890s. The Art Center is the oldest artists’ nonprofit membership organization in the Keys and features the work of more than 50 Keys artists. 

Paintings in many mediums, ceramics, sculptures, prints, and even handcrafted jewelry are on display to draw guests’ attention. Artist members offer classes to share insights into various art disciplines. In addition, the center is renowned for presenting the annual open-air Key West Craft Show and Old Island Days Art Festival.  Visit them at 301 Front Street. Call them: 305-294-1241 or check them out on the Web.

Stay in Our Key West Vacation Rentals 

Find the perfect piece of art to take home with you at one of our inspiring Key West art galleries. After discovering our dynamic arts scene, return to your vacation rental with Rent Key West Vacations. Stay in one of our rentals in the historic district, and you will be within walking distance of the Old Town galleries. Plan your Key West getaway today!