Monthly Rentals in Winter Park

Average saving of 19% on select homes for stays of 28+ nights or more.

Discover the ideal place for your extended stay in Winter Park. Whether you are vacationing with your kids and pets, working remotely, or simply in need of a change of scenery, with Vrbo you’ll find the amenities you desire, including parking and Wi-Fi. Explore fully furnished rentals ideal for short or long-stays, where you can settle in and live comfortably for a month or more in Winter Park. View all home rentals in Winter Park offering monthly discounts . Can't stay that long? Check our vacation rentals in Winter Park that offer weekly discounts.

Great home rentals for your monthly stay in Winter Park

View all vacation rentals in Winter Park offering monthly discounts

Trestle House | Ski Out Your Back Door | WP's Most Stunning Home INSTAGRAM FAMOUS!

Trestle House | Ski Out Your Back Door | WP's Most Stunning Home INSTAGRAM FAMOUS!

10/10 Exceptional! (4 reviews)
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All rentals in Winter Park

Find the perfect stay with great monthly and weekly rates

Home rentals in Winter Park with monthly discounts

Find great homes and convenient apartments in Winter Park where the host offers a discount for staying 28 nights or longer.

Only whole homes. Always Private

Book a weekly stay in a Vrbo vacation home in Winter Park: where the host offers a discount for staying 7 nights or longer.

Extended Stay in Winter Park for digital nomads and remote workers

Book accommodations with reliable Wi-Fi and dedicated work areas, ensuring you can stay productive while on the move.

Pets friendly accommodations in Winter Park

Discover homes in Winter Park away from home from which you and your pet can have a prolonged stay and explore a fascinating destination.

Vacation rentals in Winter Park with great kitchens

Discover fully furnished rentals equipped with kitchens and all the essential amenities for a comfortable stay in Winter Park lasting a month or more.

Vacation rentals in Winter Park with parking

Find great homes with parking space in Winter Park so that you can conveniently have a month-long stay and enjoy hassle-free commuting.

Wheelchair accessible vacation rentals in Winter Park

Explore accessible vacation rentals in Winter Park and discover vacation homes designed to accommodate everyone for a comfortable and inclusive extended stay.

Vacation rentals in Winter Park with pool

Enjoy a refreshing escape in a vacation rental with pools in Winter Park during your month-long getaway.