Find your adventure vacation ideal in Key West

Adventure Awaits with Historic Key West Vacation Rentals 

For active couples who thrive on adventure, outdoor exploration and the vibrancy of tropical living, Key West is a dream come true. Stunning natural beauty, a temperate climate and an array of exciting outdoor activities combine to provide the ultimate setting to fuel your passion for adventure and each other.

This February, whether you opt for a night, a week or a month (or beyond), Historic Key West Vacation Rentals offers a diverse inventory of gorgeous homes — all of which provide the perfect jumping off point for couples seeking a getaway that binds them with nature and its astounding beauty.

In addition, our team is made up of local experts who can steer couples toward the perfect blend of adventure and romance. Read on to learn how a stay in this tropical playground offers unique advantages for couples who embrace an outdoor lifestyle.

Incomparable water adventures

You’ll be surrounded by crystal-clear waters here in Key West, which makes it a paradise for water lovers, of course. Whether you’re diving into the otherworldly realm of coral reefs, paddle-boarding through serene mangroves, or skipping across sparkling waves on a jet ski, the ocean provides endless ways to stay active. Don’t miss the chance to snorkel or scuba dive in the remarkable Florida Keys National Marine Sanctuary, where you’ll encounter a vibrant universe of marine life and awe-inspiring shipwrecks.

Sunset sails and dolphin encounters

Consider chartering a sailboat for a romantic sunset cruise, or take a guided tour to spot pods of our playful dolphins. These experiences are memories in the making, and our concierge services team is ready to help you plan an adventure that perfectly pairs adventure and romance. Consider a fishing charter, a kayaking adventure or a city history and architecture tour — or a ghost tour!

Exploration on two wheels

Key West is a bike-friendly haven with charming twisting streets, scenic nature paths and minimal traffic. Rent bikes to knock around Old Town, ride along the coastline, or venture to iconic landmarks like the Southernmost Point. Cycling is not just a way to get around — it’s a practical and fun way to travel in itself.

Kayaking and eco-tours

For couples who enjoy a slower-paced adventure, kayaking through the mangroves offers a unique perspective of the island’s natural beauty and resources. Guided eco-tours allow you to connect with nature while learning about the local ecosystem.

Discover Key West’s history

Active exploration doesn’t stop at nature. You’ll find yourself wandering through the island’s historic streets, where you can tour Ernest Hemingway’s Home and Museum, or climb the Key West Lighthouse for unparalleled panoramic views. Our team can also guide you to a variety of historic and architectural tours.

Hiking at Fort Zachary Taylor State Park

Combine exploration and relaxation by hiking the trails of Fort Zachary Taylor State Park. This historic site is surrounded by stunning beaches, and the park itself is an ideal spot for a romantic picnic lunch.

Why stay with us?

After your day of adventure, you’ll need a comfortable and inviting retreat to recharge. At Historic Key West Vacation Rentals, our properties cater to active couples who value convenience, luxury, and the charm of island living. Here’s why:

Ideal locations

You’ll find yourself just steps away from Key West’s most fabulous attractions, from the famous waterfront to bustling Duval Street. You’re never far from action and adventure when you stay in one of our gorgeous historic homes.

Private retreats for unwinding

After an exhilarating day, stretch out and relax in your own private cottage in paradise. Many of our properties feature lush gardens, private pools, hot tubs and fantastic outdoor spaces perfect for unwinding together.

Fully equipped homes

From spacious kitchens to cozy living areas, our rentals provide everything you need for a comfortable stay that feels like home. Prepare meals with fresh ingredients from local markets or simply relax with a cocktail in your private outdoor space.

Check out these suggestions for an extended February vacation full of action and adventure here in Key West:

• Ashe House: This 3BR, 3.5BA beauty invites you for an extended stay in the lap of luxury. From an Old Town locale north of Truman Ave., you’ll be within biking or walking distance of some of the island’s best shops, galleries and restaurants. You’ll settle in like a local in Ashe House, a gorgeous home with high-end finishes, such as a chef’s kitchen, a wet bar, and a lush tropical landscape out back, including a pool and outdoor shower. Grill your catch of the day on the gas grill and lounge with cocktails in true Key West style around the pool.

• Azure Palm: You can’t escape the jaw-dropping ocean views from this private month-long getaway spot. The 2BR, 2BA Azure Palm exudes Key West ambience with a tiled and arched portico, soothing color palette and fabulous covered and furnished oceanfront balcony. You’ll fall asleep to the melody of the sea after a full day of tennis, fitness and swimming. Here you’ll be near the White Street Pier, Higgs Memorial Beach Park and the Key West Nature Preserve. Not to mention, all the nightlife of Duval Street is just a short walk away.

• Three Arches in Paradise: You’ll want to stay more than a month in this gorgeous 3BR, 3.5BA fully renovated historic home. Draped in tropical orchids and Bougainvillea, this gorgeous property offers high-end décor and a soft coastal color palette, with mature palm trees and lush landscaping. Exit French doors to a full outdoor kitchen, living area, bar and private pool with a water feature. Here at Three Arches in Paradise, you’ll find yourself just four blocks from Duval Street and within walking distance of Higgs Beach and White Street Pier. 

Plan your active escape today!

This February, couples who seek the thrill of the outdoors will find in Key West more than a destination — it’s a playground. Whether you’re diving into the azure depths, cycling through historic streets or exploring the beauty of nature, this island offers endless ways to stay active while deepening your connection with your partner. Visit Historic Key West Vacation Rentals and start planning your adventure escape in paradise. The perfect home base awaits you in the gorgeous tropical destination of Key West!