Luxury Vacation Rentals in the Heart of Key West
Welcome to Your Keys Vacation Rentals, where handpicked, high-end island homes immerse you in the best of Key West’s vibrant culture. Each property boasts distinct architectural charm—from contemporary beach houses with private plunge pools to elegantly renovated historic cottages. Whether you’re savoring the gourmet kitchen amenities or relaxing on breezy verandas, our thoughtfully designed spaces bring loved ones together for an unforgettable, luxurious retreat.
Spend your days exploring the legendary Duval Street for world-class dining and shopping, or strolling the historic seaport before embarking on a fishing charter or watersport adventure. In the evening, gather on your private patio for fresh-caught seafood or venture out for local festivities. With Your Keys Vacation Rentals, you’ll experience the authentic Key West lifestyle—all while enjoying the comfort, style, and exclusivity of a truly first-class vacation home.
Casa Catalina: A Luxurious Key West Escape Just Steps from Duval Street!
- Guests: 6
- Size: 1596ft²
Nestled just steps from the renowned Duval Street, Casa Catalina is a newly renovated classic conch-style residence, seamlessly blending historic charm with contemporary comforts. This spacious abode, exceeding the typical dimensions of cigar makers’ cottages, boasts a generously sized open-plan layout encompassing the living, dining, and kitchen areas, opening up to a large deck and pool. Casa Catalina provides an ideal retreat for your Key West getaway, offering two bedrooms, two baths, and accommodation for up to six guests. Enjoy the island breeze from your private outdoor space, unwind by the pool, and soak in the laid-back luxury that makes Casa Catalina a one-of-a-kind tropical escape in the heart of Old Town Key West.
- View: 2 Bedroom, 2 Bath Just Off World Famous Duval Street In The Heart Of Old Town KW
- Amenities: Air Conditioning, Beach Towels, Bedroom linens, Cable TV, Coffee Maker, Deck Patio, Dinning Table, Dishes and Utensils, Dishwasher, DVD Player, Flat Screen TV, Grill, Hair dryer, Heating, Iron and Board, Kitchen, Microwave, Oven, Printer, Private Pool, Refrigerator, Sonos Bluetooth + WIFI Sound System, Stove, Toaster, Washer Dryer, Wi-Fi
- Downstairs Bedroom: 1 Queen Bed, Full Bath
- Upstairs Bedroom: 1 King Bed, 2 Twin Beds, Full Bath
- Living Room: Queen Sleeper Sofa
Brisa Azul – Modern & spacious historic home with private pool and parking
- Guests: 6
- Size: 1672ft²
Welcome to Brisa Azul (Blue Breeze), a beautifully renovated historic home in the heart of Old Town Key West. Up to 6 guests can unwind in 2 bedrooms plus a cozy den (with convertible sofa), and enjoy 3 full baths, a soaring living area, and fold-away doors leading to a private backyard oasis. Lounge by the heated/chilled saltwater pool, relax under the gazebo with built-in grill and bar area, and take advantage of Wi-Fi, modern appliances, and TVs in every room. Located near the historic Seaport and just a short stroll from Duval Street’s world-class dining and nightlife, Brisa Azul is the perfect base for an unforgettable island getaway with all the modern comforts and tropical charm you could ask for.
- View: Modern and Spacious Historic Home with Private Pool and Off Street Parking
- Amenities: Air Conditioning, Beach Towels, Bedroom linens, Cable TV, Coffee Maker, Deck Patio, Dinning Table, Dishes and Utensils, Dishwasher, DVD Player, Flat Screen TV, Grill, Hair dryer, Heated Pool, Heating, Iron and Board, Kitchen, Microwave, Off Street Parking, Oven, Pavillion, Pool Chiller, Printer, Private Pool, Refrigerator, Smart TV, Stove, Toaster, Washer Dryer, Wi-Fi
- Primary Bedroom: 1 King Bed, Full Bath, Downstairs
- Secondary Bedroom: 1 King Bed, Full Bath
- Den Bedroom: 1 Queen Sleeper Sofa, Downstairs, Full Bath
Prices start at: $695 per night
Casa Catalina: A Luxurious Key West Escape Just Steps from Duval Street!
- Guests: 6
- Size: 1596ft²
Nestled just steps from the renowned Duval Street, Casa Catalina is a newly renovated classic conch-style residence, seamlessly blending historic charm with contemporary comforts. This spacious abode, exceeding the typical dimensions of cigar makers’ cottages, boasts a generously sized open-plan layout encompassing the living, dining, and kitchen areas, opening up to a large deck and pool. Casa Catalina provides an ideal retreat for your Key West getaway, offering two bedrooms, two baths, and accommodation for up to six guests. Enjoy the island breeze from your private outdoor space, unwind by the pool, and soak in the laid-back luxury that makes Casa Catalina a one-of-a-kind tropical escape in the heart of Old Town Key West.
- View: 2 Bedroom, 2 Bath Just Off World Famous Duval Street In The Heart Of Old Town KW
- Amenities: Air Conditioning, Beach Towels, Bedroom linens, Cable TV, Coffee Maker, Deck Patio, Dinning Table, Dishes and Utensils, Dishwasher, DVD Player, Flat Screen TV, Grill, Hair dryer, Heating, Iron and Board, Kitchen, Microwave, Oven, Printer, Private Pool, Refrigerator, Sonos Bluetooth + WIFI Sound System, Stove, Toaster, Washer Dryer, Wi-Fi
- Downstairs Bedroom: 1 Queen Bed, Full Bath
- Upstairs Bedroom: 1 King Bed, 2 Twin Beds, Full Bath
- Living Room: Queen Sleeper Sofa
Brisa Azul – Modern & spacious historic home with private pool and parking
- Guests: 6
- Size: 1672ft²
Welcome to Brisa Azul (Blue Breeze), a beautifully renovated historic home in the heart of Old Town Key West. Up to 6 guests can unwind in 2 bedrooms plus a cozy den (with convertible sofa), and enjoy 3 full baths, a soaring living area, and fold-away doors leading to a private backyard oasis. Lounge by the heated/chilled saltwater pool, relax under the gazebo with built-in grill and bar area, and take advantage of Wi-Fi, modern appliances, and TVs in every room. Located near the historic Seaport and just a short stroll from Duval Street’s world-class dining and nightlife, Brisa Azul is the perfect base for an unforgettable island getaway with all the modern comforts and tropical charm you could ask for.
- View: Modern and Spacious Historic Home with Private Pool and Off Street Parking
- Amenities: Air Conditioning, Beach Towels, Bedroom linens, Cable TV, Coffee Maker, Deck Patio, Dinning Table, Dishes and Utensils, Dishwasher, DVD Player, Flat Screen TV, Grill, Hair dryer, Heated Pool, Heating, Iron and Board, Kitchen, Microwave, Off Street Parking, Oven, Pavillion, Pool Chiller, Printer, Private Pool, Refrigerator, Smart TV, Stove, Toaster, Washer Dryer, Wi-Fi
- Primary Bedroom: 1 King Bed, Full Bath, Downstairs
- Secondary Bedroom: 1 King Bed, Full Bath
- Den Bedroom: 1 Queen Sleeper Sofa, Downstairs, Full Bath
Prices start at: $695 per night
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Your Favorite Vacation Rentals + Expert Guidance for Buying & Selling in Key West
Experience the best of island living with Your Keys Vacation Rentals and Your Keys Real Estate. Whether you’re planning a short-term stay in a charming cottage or ready to buy your dream home by the sea, our dedicated team provides the expertise and personal touch you need. Enjoy a seamless transition from unforgettable getaways to owning your own slice of paradise.