Key West: The Ultimate Weekend Getaway for Couples

Romantic Escapes with Historic Key West Vacation Rentals

At the southernmost tip of the United States lies Key West, a tropical paradise brimming with charm, history and romance. Couples looking to escape daily life and kindle some romance will find that a weekend in Key West offers an alluring mix of relaxation and adventure. Add to that the charm of a cozy vacation cottage from Historic Key West Vacation Rentals, and you’ve sealed the ultimate romantic retreat.

In 2025, Valentine’s Day falls on a Friday, so why not plan the ultimate long weekend getaway in celebration of love? Historic Key West Vacation Rentals offers something for every couple in our portfolio of fabulous nightly, weekly and extended-stay rentals.

Why Key West?

This scenic five-square-mile island offers distinct neighborhoods, each with its own individual charm. You’ll wander streets lined with classic Conch cottages, stately Victorian mansions and gorgeous mid-century modern homes. Historic Key West Vacation Rentals puts you right in the middle of all the action of Old Town Key West, where you’ll take to the streets and soak up the ambience of this fascinating destination together. Here, you’ll encounter all the unique charms of this tiny island-city, waiting around every corner, nook and cranny. And, of course, in Key West you’re never far from the beach, with endless views of spectacular sunsets, azure waters and silky white sand.

Stunning scenery

It’s hard to overstate the effect of Key West’s breathtaking sunsets, turquoise waters, and lush tropical landscapes. You won’t be able to resist kicking off your shoes and strolling barefoot and hand-in-hand along a sandy stretch of beach or sipping cocktails at a quaint waterfront bar — every moment creates a postcard-worthy memory.

Vibrant culture

Key West is unique in the world for its lively atmosphere, its blend of Caribbean influences and historic charm — all working together to create the ultimate magical setting for romance. Duval Street beckons with eclectic shops, galleries, and entertainment, while quieter neighborhood streets showcase the island’s fascinating architecture and charming gardens.

Alluring adventure

Couples seeking an outdoor adventure will find no shortage of opportunities in Key West. Snorkel among coral reefs in the island’s crystal clear waters, embark on a sunset sail, and explore hidden coves by kayak. Every adventure brings you closer together.

Romantic dining

It’s tough to choose from fine dining under the stars to casual oceanfront eateries that feature popular local fare. Key West’s culinary scene offers endless opportunities to experience and savor an impressive array of food. You’ll unwind as you share a tropical cocktail, watch the sunset and gaze into each other’s eyes.

Let Historic Key West Vacation Rentals pave the way

A romantic weekend vacation in Key West is elevated when you stay in a cozy private cottage imbued with island charm and that offers all the comforts of home. Here’s why our properties are ideal for your special couple’s Valentine’s retreat:

Unique, cozy cottages

Our historic homes provide the perfect blend of charm and luxury. These homes are designed with couples in mind — and feature intimate spaces, lush gardens and inviting interiors.

Privacy and tranquility

Unlike impersonal crowded hotels, our lovely vacation homes offer secluded settings where you can truly relax together. Every detail is meant to help you enjoy personal moments, such as mornings with coffee on a private veranda or evenings in a bubbling hot tub under the stars.

Ideal locations

Our historic homes are centrally located, making island exploration a breeze. From your doorstep, you can easily stroll or bike to all Key West’s most exciting local attractions, beaches and restaurants — no car necessary.

Special weekend rates

Plan your romantic Valentine’s getaway with around our weekend specials, featuring discounted rates on select properties offering tropical elegance and plenty of space to unwind together.

Plan your romantic weekend today

Key West is more than just a fabulous destination — it’s an experience with the power to rejuvenate and rekindle romance. This idyllic setting and the charm of our historic vacation homes is a winning combination for couples longing to create lasting memories.

Don’t wait — book your long Valentine’s Day weekend escape with Historic Key West Vacation Rentals, and start counting down the days to your tropical paradise retreat. Visit Historic Key West Vacation Rentals to find the perfect romantic cottage for your dream getaway. Here are some of favorites to get you started in your search:

• Potter’s Cottage: Spend a long and romantic Valentine’s weekend by soaking up island charm in this darling 2BR, 2BA hideaway. Starting with the rocking chair on its front porch, you’ll be captivated by cozy Potter’s Cottage, which offers all the comforts of home, along with a lovely private outdoor space. Enjoy happy hour in the cocktail pool, surrounded by loungers and Adirondack chairs, an outdoor shower and a furnished lounge area with a dining table and chairs. Just steps outside the door you’ll be able to explore all the attractions of Old Town Key West, including beaches, restaurants and shops, on foot.

• Petite Maison: Celebrate a long, luxurious Valentine’s Day weekend and relax in Key West style in Petite Maison, a 2BR, 2BA property featuring gorgeous living spaces with a reverse floor plan and chic décor. Step through the French doors and sip wine with your sweetheart on the comfortably furnished veranda out back. You’ll find yourself just a short distance from Zachary Taylor Beach, the vibrant cafes and nightlife of Duval Street, the Southernmost Point and the Key West Butterfly and Nature Conservatory.

• Chavez House: This Valentine’s Day, spend the weekend embracing the indoor-outdoor island style of fabulous Key West. You’ll enjoy a gorgeous private outdoor space, complete with a covered lanai, a beautiful pool with a waterfall feature, comfy loungers and a vaulted ceiling with a tropical fan. Lounge away your time in this romantic lush setting, then retreat to the king bedroom featuring Dade County pine walls and private ensuite bathroom. The historic 3BR, 2BA Chavez House features a fabulous dining room and a gourmet kitchen for cooking up a romantic dinner for two. Or take a leisurely stroll into Old Town or to the Historic Seaport for a nightcap.