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 Honeymoon Activities and Accommodations

Are you looking for a tropical destination for your honeymoon without traveling abroad? Then look no further than Key West, the southernmost city in the continental United States! Known for our picturesque beaches, consistently warm weather, captivating sunsets, rich history, and diverse cuisine, there is something for every couple in our slice of paradise. Elevate your Key West honeymoon with Rent Key West Vacations, and tailor your romantic getaway to be as adventurous or relaxing as your heart desires!

7 Key West Honeymoon Activities

Key West offers attractions for every type of traveler, whether you are a beach bum or a history buff! Get around town with Old Town Trolley Tours and explore the area’s top attractions with a local guide. Here are a few of our favorite activities to put on your Key West honeymoon itinerary:

Explore Duval Street hand in hand and stroll past colorful shops, art galleries, and famous restaurants. Stick around for the famous Key West Sunset Celebration at Mallory Square and end the night with fantastic live entertainment!
Nothing says romance like spending time together on our picturesque beaches. Visit Smathers Beach or Clarence S. Higgs Memorial Beach, where you can enjoy suntanning, snorkeling, and swimming. If you want some added romance, we recommend reserving an oceanfront picnic with Lovely Luxury Picnics!
Sign up for a romantic champagne sunset cruise with Catamaran Echo. Sail into the sunset together while sipping champagne with a delicious charcuterie board. They also offer private charters and eco tours where you can witness wild dolphins!
Learn about local history and famous residents together at our Key West museums like the Ernest Hemingway Museum, Truman Little White House, Mel Fisher Maritime Museum, and Fort East Martello Museum.
Treat yourself to a couples massage at Prana Spa in their intimate and private couples’ rooms. This is the perfect setting for healing your mind, body, and soul together!
If you are looking for ways to get on the water rather than it, we have a wealth of watersports waiting for you! Explore our waterways with guided trips with Fury Cat, including snorkeling, sunset cruises, eco-tours, parasailing, and jet skiing.
End the day with a romantic dinner and indulge in fine dining at Latitude’s, a beautiful beachfront restaurant serving fresh seafood. Then head to the Better than Sex Dessert Restaurant and share mouthwatering desserts in an intimate speakeasy setting!

Plan Your Key West Honeymoon with Rent Key West

Plan the perfect Key West honeymoon with Rent Key West Vacations, one of the longest-standing vacation rental companies on the island. Enhance your stay with our concierge services like gourmet gift baskets, in-home chef services, and floral arrangements.

We offer the perfect romantic one-bedroom vacation rentals, ideal for couples honeymooning on the island. Stay in affordable properties like the one-bedroom Portside Suite, just steps away from Duval Street. Or experience luxury at our Casa Atlantica rental on beautiful Higgs Beach, with elevated amenities like a tiki hut on the water. With Rent Key West Vacations, couples can relax, unwind, and create lifelong memories in this enchanting tropical paradise!