The 7 Best Snowbird Luxury Vacation Rentals

Miss Sunshine Monthly Rental
by Historic Key West Vacation Rentals

The seven best Snowbird luxury rentals in Key West are available through Historic Key West Vacations Rentals. They're the best because they're located in this tropical paradise surrounded by crystal blue waters separated from the high octane speed of life on the mainland. All laid back, relaxed and ready for your long term winter stays. These spacious and private luxury vacation homes have been carefully selected with your winter enjoyment in mind. Key West winter weather is so pleasant, mild and warm you'll be out and about enjoying many of the same exciting adventures in recreation, the arts, culinary and relaxation as you do during any other warm weather vacations.  Which luxury vacation rental is best for you? Let's take a closer look.

Miss Sunshine-NEW Monthly Rental 3 Bedrooms 3 Bath Sleeps 6

Find serenity in this lustrous, two-story, updated Key West Monthly Rental. This monthly rental checks all of the boxes offering a Private pool surrounded by lush foliage and Brazilian teak decking. Lounge chairs, dining table and outdoor shower, are provided for your enjoyment. Did we mention It's pet-friendly, too! 

Bahari House, Seaport-NEW Monthly Rental 2 Bedrooms 3 Bath Sleeps 6



Enjoy the beautiful outdoor area and covered, private covered patio with grill in the rear of this pet-friendly home. Both the front porch and second story balcony are great for people watching. 

Casablanca Too - Nightly Rental 1 Bedroom 1 Bath Sleeps 2

Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too. This unpretentious home is comfortably furnished and ready to welcome you and your fur baby. Normally a nightly rental, through special arrangement with its owner, this intimate luxury rental is available for long term stays in November and December 2022.

Copa Cabana - Monthly Rental 2 Bedrooms 1.5 Bath Sleeps 4

This home’s white picket fence and rocking chair front porch beckon you to come inside. Explore the uniqueness of this Key West Vacation Rental with a Private Pool - updated property including its location in Bahama Village, private pool, and pool house.

Fish Camp - New Monthly Rental 3 Bedrooms 3 Bath Sleeps 8

A unique feature of this home is its canal-front location complete with seawall and a 6'X16' dock to tie up your boat. The large outdoor space includes a covered patio, TV, outdoor kitchen, picnic table, a brand new pool and plenty of space. 

Inn Cogneato Cottage - Monthly Rental 2 Bedrooms 2 Bath Sleeps 4

This  is a newly renovated beautiful home located in one of the oldest parts of Historic Key West. Surrounded by a white picket fence, this home is perfect for a couple that plans on entertaining visiting guests or family during their stay.  The new saline pool measures 14 x 8 feet, is 5 feet deep, has an in pool bench for sitting and a beautiful custom waterfall!

Magical Margaret - NEW Monthly Rental 4 Bedrooms 5 Bath Sleeps 10

Enjoy the private outdoor area with saline pool and hot tub. A gas grill, dining tables and chairs and outdoor shower complete the space.


Don't think you can take the time off for a warm, winter vacation? No worries, as each of our Key West luxury vacation rentals come with a complete set of concierge services that include high speed Internet, work spaces for remote working and learning, and everything you need to stay connected with your mainland life. Can't wait for winter to begin your long term luxury stay with us? No worries there either. We have a full complement of long term luxury vacation rentals available for immediate occupancy. We'll just call it your "fall into winter progressive work, stay and play fantasy getaway." It's just that simple. Make your own reservations right on our website or give our long term luxury stay vacation planners a call at 305.296.1010. We're happy to help plan your long term visit and we can even provide you with luxury relocation services through our real estate division. Yes. It really is just this simple. 


Explore more of our Key West rentals for the perfect vacation to the Flordia Keys.

Key West Condo Rentals

Key West Weekly Rentals

Key West Nightly Rentals