Key West Vacation Rentals With Swimming Pools

Pack your swimsuit, sunglasses, and sunscreen for these Key West vacation rentals. The majority of our properties have private or shared swimming pools accessible to guests, complementing the perfect island getaway. Ranging from one bedroom to five bedroom homes, Preferred Properties offers a wide selection of rentals to choose from. Unique design elements and amenities along with an accessible pool create an unforgettable vacation experience.

For a single guest or a couple, Tree Tops is a single bedroom vacation rental located near Old Town and the Truman Annex. Tree Tops has a full kitchen, spacious rear balcony, and easily accessible parking, among other amenities. For pool lovers, the shared pool is right outside and heated in the winter.

Two and three bedroom options are also available. Elizabeth’s Secret, Pineapple Cottage, English House, Tranquility, and Corazon are just a few of our two and three bedroom accommodations. From Dupont Retreat’s brand new dishes, cookware, and bedding to Golf Villa’s proximity to the Key West Golf Club and Golf Course, you’ll find variety and charm along with sparkling pools.

Guests desiring four or five bedroom vacation rentals will find private pools in all available accommodations including Casa Royal, Conch Heaven, Casa do Sol, and Mango Gardens. Casa do Sol offers separate entrances to each cottage for groups who prefer a bit more privacy, while the historic charm and private deck of Mango Gardens provide an attractive and comfortable abode for vacationers.

Preferred Properties offers many other rental amenities in addition to private or shared pools. Convenient locations within walking distance to Old Town and Duval Street, well-maintained interiors, and a wide selection make these homes stand out from other island rentals. Whether you’re seeking an intimate getaway or a large family space, you can find a comfortable and colorful home to meet your needs.