Indulge your senses at Fantasy Fest! Find your perfect stay with Historic Key West Vacation Rentals

Every October, Key West comes alive with color, music and imagination for one of the island’s biggest events of the year: Fantasy Fest. This 10-day extravaganza (Oct. 17-26) draws visitors from around the world for a whirlwind of themed parties, dazzling costumes, parades, live music, and unforgettable street celebrations.

From the famous Masquerade March to glamorous costume balls, the outrageous parade down Duval Street and an elaborate street fair, Fantasy Fest 2025 promises to be bigger and bolder than ever.

If you’re planning to join the fun, now is the time to secure your stay. The good news? A handful of our most charming and comfortable Key West vacation rentals near Duval Street remain available. Each of these homes offers the perfect balance of location, amenities and authentic island style — so that you can celebrate all day and then retreat to your own private oasis each night.

Here are six incredible homes from Historic Key West Vacation Rentals that are ready to host your Fantasy Fest adventure:

• Chick-a-Pea: When the energy of Fantasy Fest has you dancing all night, Chick-a-Pea provides the perfect place to recharge with friends. This 4BR, 2.5BA Old Town gem features a private pool surrounded by lush tropical landscaping, ideal for cooling off after a parade or simply floating under the stars. Inside, you’ll find chic coastal décor, a comfortable living space, and modern amenities that make relaxing effortless. Best of all, Chick-a-Pea is just minutes from Duval Street—close to the action, yet tucked away for privacy when you want it most.
• Grand Maison: Traveling with a group of friends? Grand Maison offers the ultimate combination of space and luxury for the perfect Fantasy Fest getaway. With its soaring ceilings, elegant design, and expansive layout, this 4BR beauty feels every bit as grand as its name suggests. The gourmet kitchen makes entertaining a breeze, while the outdoor living space is perfect for pre-party cocktails or a quiet morning after a big night out. Whether you’re gathering for the Masquerade March or winding down by the pool, Grand Maison is the perfect headquarters for your crew.
• Lilly’s Pad: Playful, bright and brimming with charm, Lilly’s Pad is an irresistible retreat for festival-goers. The home’s whimsical design reflects the fun-loving spirit of Fantasy Fest itself, while the inviting pool and sunny outdoor spaces create the perfect backdrop for afternoon lounging. Just steps away from Old Town’s buzzing streets, this 3BR refuge gives you the best of both worlds: a restful hideaway and easy access to all the action.
• Poinciana Treetop: For guests seeking a quieter perch amid the Fantasy Fest buzz, Poinciana Treetop offers a refreshing escape. This elevated hideaway comes with a breezy open floor plan and a private balcony tucked among the palms, making it easy to soak up the tropical air. Ideal for couples or small groups, the 1BR (3 guests) home is close enough to join the revelry on Duval Street but feels like a sanctuary when you return. Festival fun by day, peaceful retreat by night — Poinciana Treetop delivers both.
• Southard Comfort: A stay at Southard Comfort brings exactly that — comfort wrapped in classic Key West style. This historic home blends timeless architecture with modern touches, creating a welcoming space for groups of friends or families. With spacious bedrooms, a stylish interior, and a private outdoor area, this 3BR gem makes it easy to relax and recharge. Its location, just blocks from Duval Street, puts you within walking distance of Fantasy Fest highlights while still offering a restful escape when you need to slow down.
• Butterfly Cottage (weekend only): If you’re only planning a weekend escape to Fantasy Fest, Butterfly Cottage is the place to land. This cozy retreat is available for a limited-time stay and offers all the essentials: charming Key West décor, a private pool, and a prime location close to the festivities. Whether you’re here for the Fantasy Fest parade or just a whirlwind of parties and events, Butterfly Cottage provides a stylish and comfortable home base for your short-but-sweet adventure.