Vacation Rentals
35 properties available
Leo’s Lodge | Newly Updated!
Leo’s Lodge offers an intimate and updated retreat just a few blocks from the famous Duval Street. The island of Key West, with its enchanting allure, invites everyone to enjoy its beauty, and Leo’s Lodge is a perfect base for making the most of your stay.
The Space:
Though small, Leo’s Lodge provides everything you
Salvador\'s Seclusion – Cozy Studio Retreat with a Heated Pool!
Welcome to Salvador\'s Seclusion, a charming micro-efficiency located in the heart of Key West! This serene oasis offers all the essentials for a delightful stay in paradise, just minutes away from the vibrant arts scene of Duval Street. Once a haven for artists, this space now invite
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 kit
The Salt Cay | Updated! Stunning Sunset View, Pool!
Escape to The Salt Cay, a serene, beautifully updated, and well-appointed 2-bedroom condo nestled in the tranquil Sunrise Suites community on east side of Key West. Just a mile from the beach, this charming getaway offers the ideal combination of relaxation and adventure. Whether you\'re lounging
Wahoo Way | Charming Hideaway On Duval Street!
Escape to Wahoo Way for an unforgettable couple’s retreat in Key West! This delightful suite is perfectly situated on vibrant Duval Street, placing you just moments away from the finest nightlife, dining, and attractions the island has to offer. Plus, the iconic Southernmost Point and the beach are ju
Duval Street Retreat | Dog-Friendly Home with Hot Tub, WiFi, & Private Parking
Duval Street Retreat is your ideal Key West escape, perfectly situated in the heart of the island’s historic district! With a shared hot tub, patio space for grilling, and easy access to the best of Key West, this home offers the perfect mix of comfort and convenience.
Welcome to Pilar Cottage, a charming studio located within the peaceful Harbor Walk Hideaways complex in Key West\'s Historic Seaport district. This cozy one-bedroom, one-bathroom retreat features upscale furnishings and offers a small shared dipping pool, making it a perfect spot to soak up the Florida sun.
Comfort and Amenities:
Pilar Cottage is
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
Atocha Cottage at Harbor Walk Hideaways
Welcome to Atocha Cottage, a serene getaway nestled within the charming Harbor Walk Hideaways complex in Key West\'s Historic Seaport district. This delightful 2-bedroom, 1-bathroom cottage combines modern comfort with a prime location, just steps away from local attractions and the beautiful waterfront.
Co
Ritaville | New! Waterfront Paradise with Private Pool
Experience a serene retreat at Ritaville, a stunning waterfront home in Geiger Key, Florida. This expansive two-story, 4-bedroom, 3-bathroom getaway offers the perfect mix of relaxation and adventure. Enjoy breathtaking views, your own private pool, and direct boat access right from your backy
Sailor’s Sanctuary | Stunning Updated Condo Near Duval Street!
Welcome to Sailor’s Sanctuary, a beautifully renovated ground-floor condo nestled in the heart of Key West’s historic Old Town. Located in the prestigious Truman Annex, this charming two-bedroom retreat offers a perfect balance of privacy, comfort, and convenience. Just steps from Duva
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Heron Suite is an excellent choice for your next adventure in Key West! This welcoming suite is part of Southernmost Sanctuary, providing easy access to shared hot tubs and a delightful patio to enjoy the island vibe. With a kitchenette, cable TV, and complimentary WiFi, you\'ll fee
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