Nightly properties
50 properties available
Southernmost Retreat | Two Dog-Friendly Homes with Hot Tubs, WiFi, & Private Parking
Southernmost Retreat is the perfect home base for your Key West getaway! Comprising two beautifully appointed homes located in the heart of Key West\'s vibrant historic district, this combined property offers the ideal mix of comfort, convenience, and relaxation.
Underwater Cabana at Custom House Inn | Stay on Duval Street!
Experience the heart of Key West with a stay at the Underwater Cabana, one of five uniquely designed suites at the Custom House Inn. Nestled on the iconic Duval Street, this aquatic-themed suite offers the perfect blend of comfort, style, and location. Whether you\'re here to explore th
Welcome to Harborwalk Hideaways!
Overview:
Discover Harbor Walk Hideaways, a beautifully renovated vacation rental complex nestled in the Historic Seaport district of Old Town Key West. This sought-after destination features three charming cottages—Atocha, Pilar, and African Queen—each named after legendary vessels that frequented Key West. Ideal
Carey\'s Corner | Updated Studio with Heated Pool
Carey\'s Corner is a cozy, updated studio nestled in the heart of Bahama Village. Key West may be small, but its magic is immense, and Carey\'s Corner is the perfect base for experiencing it all—from the relaxing poolside to the lively nearby attractions.
The Space:
This second-floor studio featur
Duval Delight | Recently Remodeled Condo on Duval!
Duval Delight is your gateway to enjoying the best of Key West! Located on the quieter end of iconic Duval Street, this beautifully remodeled loft-style condo offers the ideal setting for a tropical getaway. Whether you\'re here for the culture, cuisine, or the famous sunsets, Key West\'s magic is
Truman @ Duval - Unit C | Cozy Studio Perfect for Couples
Experience your perfect romantic retreat, offering a charming and vibrant atmosphere right in the heart of downtown Key West! Whether you\'re here for the local culture, waterfront activities, or a peaceful island escape, this cozy condo is the ideal home base to experience it all.
The Amb
Experience the vibrant charm of Key West with a stay at Sea Esta Suite, a stunning two-story townhouse located in the exclusive Duval Square condominium complex. Perfectly situated at the intersection of Truman Avenue and Duval Street, this vacation rental puts you just steps away from world-class dining, shopping, and iconic attractions like the S
Casa De Cubana | New! Historic Cuban-Style Home Steps from Duval Street
Discover the charm and elegance of Key West at Casa De Cubana, a newly constructed 2-bedroom, 2.5-bathroom home that blends the rich history of Old Town with modern comforts. Located just half a block off the iconic Duval Street, this single-story elevated home draws inspirati
Escape to the vibrant heart of Key West and stay at the charming Claude Monet Suite, located just a few blocks from famous Duval Street. This micro-efficiency studio offers a cozy retreat for up to four guests, with access to a tranquil pool and spacious sundeck. Once a creative hub for traveling artists, The Galleria has now been transformed into
Chagall\'s Corner | Newly Remodeled!
Chagall\'s Corner offers a relaxing, second-floor retreat in the heart of Key West. This newly remodeled micro-efficiency is perfect for those seeking a serene escape while still being close to all that makes Key West magical and unique.
The Space:
This studio features a Queen bed, en-suite bathroom, and a ki
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Osprey Suite is the perfect choice for your next getaway in Key West! This charming suite is part of Southernmost Sanctuary, offering easy access to shared hot tubs and a delightful patio to soak up the island atmosphere. Equipped with a kitchenette, cable TV, and complimentary WiFi, you\
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Egret Suite is the perfect spot for your next adventure in Key West! This inviting suite is part of Southernmost Sanctuary, providing easy access to shared hot tubs and a delightful patio to enjoy the island vibes. With a kitchenette, cable TV, and complimentary WiFi, you\'ll feel right at
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