Luxury Key West Monthly Snowbird Rentals

azur palm pool
by Historic Key West Vacation Rentals

Four of our most luxurious Key West Snowbird Vacation Rentals for 2023/2024 are fully furnished premier homes that are perfect for long-term month stays in Key West, winter vacations and remote working assignments. In fact, our luxury vacation planners are dedicated to matching ideal accommodations for you, your family, your friends and your work travel groups. Immerse yourself in the warm and tropical vibes all month long and experience what local living in Key West can offer.  Historic Key West Vacation Rentals offers numerous luxury properties in the Gulf of Mexico to make your stay hassle-free and filled with the best that Key West and the Florida Keys have to offer. 

Luxury Key West Snowbird Rentals

Azur Palm-NEW Monthly Rental

Luxurious finishes, tile floors, gorgeous lighting, and ceiling fans adorn the stylishly furnished rooms. Enjoy the cool breezes and breathtaking sunsets and sunrises from your balcony. If you have been longing to indulge in a vacation with a view from a beautiful living room and be lulled to sleep by the sounds of the sea, this upscale oceanfront home is waiting for you!

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Sunshine and Shenanigans- NEW Monthly Rental

This home with Bahama shutters and hardwood floors is filled with island charisma. As you enter from its covered front porch, you have a sight line to the rear of the home. The retractable sliding glass doors provide natural light and direct access to the rear deck and guest cottage.

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Ashe House - Monthly Rental

As you enter the home via its white picket fence and comfortable front porch, you will be uplifted by sunshine. Hardwood floors and high-end finishes are reflected in this home while a bit of Key West charm is revealed. A wall of glass spills out onto the beautiful blue pool area. Enjoy a day or night swim, with plenty of privacy and loungers. Cook up your catch of the day on the outdoor grill.

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Villa Azul - Monthly Rental

Located in the heart of Old Town Key West, this two-story home with a first-floor bedroom is ideal for the entire family. Your guests or young adults may enjoy the privacy of their own pool house with an ensuite half bath and delightful outdoor shower.

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Create your own winter vacation when you reserve one of our luxury Key West Vacation Rentals from our monthly collection or with our planners at 305.296.1010. You'll live like a Key West local and feel all the comforts of home as soon as you settle into your seasonal rental. Winter is always most enjoyable when it's warmed up by our tropical sunshine. Let us help you reserve yours today!