Monthly Rentals in Winter Park

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Superhost

Guesthouse in Winter Park

4.95 out of 5 average rating, 56 reviews

Winter Park City 32789 Mile to Park Ave & Rollins

ClarkeRating, 5 stars4 months ago

As always a great stay. Please read my previous reviews which provide finer details. I recommend staying at this location to anyone.

Superhost

Condo in Winter Park

4.83 out of 5 average rating, 98 reviews

Lovely Winter Park Home close to Hospitals !

MichaelRating, 5 stars1 month ago

This was my 4th time staying there to visit family who live in the area. I’d say picking the same place 4 times is the ultimate complement of the condo unit.

Superhost

Apartment in Winter Park

4.88 out of 5 average rating, 112 reviews

Apt G - Poolside in the Heart of Winter Park

RickyRating, 5 stars3 weeks ago

Everything was organized and clean the place was beautiful .

Superhost

Guesthouse in Winter Park

4.95 out of 5 average rating, 61 reviews

Winter Park Oasis B

RickRating, 5 stars4 months ago

What a great place to stay. Well stocked for extended stays, It’s close to everything and I can’t say enough about how amazing Rachid is. I would certainly recommend this place to everyone looking for a safe, quiet, clean home to stay at. Couldn’t ask for a better host, they are great folks bill

Explore all

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & traveling professionals

Comfortable accommodations for nomadic and remote working professionals with wifi and dedicated work spaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Popular amenities for monthly rentals

Kitchen

Wifi

Pet friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Stay near Winter Park's top sights

Orlando Science Center124 locals recommend

Orlando Museum of Art58 locals recommend

Harry P. Leu Gardens83 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.