Monthly Rentals in Winter Park

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

Nearby monthly rentals

Guest favorite
Condo in Winter Park
4.93 out of 5 average rating, 29 reviews

Charming 2/1 Condo on a Lake in Winter Park

LindaRating, 5 stars12 months ago
Jenifer's home was extremely clean; we felt comfortable there as soon as we walked in. Her condo is also very well located. We really enjoyed our morning walks for coffee and our walks into the historic downtown. And Jennifer was very accommodating, letting us check in an hour early. I would highly recommend Jennifer's condo if you are visiting Winter Park!
Guest favorite
Condo in Winter Park
4.82 out of 5 average rating, 94 reviews

Lovely Winter Park Home close to Hospitals !

ChrisRating, 5 stars1 week ago
The condo was exactly as described. It was unfortunate the pool and hot tub were not heated making them unavailable during our stay, however this is not a reflection on Gabriel. The condo was clean, well stocked for our needs and in a well maintained complex . Close to several areas of interest.
Top guest favorite
Guest suite in Winter Park
4.96 out of 5 average rating, 251 reviews

Atmospheric Studio in the Garden

ClarkRating, 5 stars3 weeks ago
Although only a studio apartment, Justin and Maryanne's unit was very open and bright, completely comfortable, and perfect for me. The two French doors opening to the backyard patio made it seem larger than it was. Everything was well thought out and appointed, and I was completely content during my month long stay. The kitchen area is nice but basic, with a small two burner convection cooktop and a microwave. I ended up doing quite a bit of takeout and dining out anyway, so it was completely adequate for me. The neighborhood also was safe, beautiful, well located in Winter Park, and very walkable. I walk 3-4 miles a day for exercise, and I almost never tired of the area. There's a nice mix of charming historic homes, stylish new builds, and a smattering in nice condo buildings, all in a leafy setting. Shopping is only a short distance away. All in all I had a delightful stay, and would highly recommend it to solo travelers and couples.
Guest favorite
Apartment in Winter Park
4.95 out of 5 average rating, 291 reviews

Retro Palm Beach-Style Boudoir

AlexandraRating, 5 stars2 months ago
Upon check in, there were a few hiccups, nothing major, but I brought it to Jaycelle's attention and she was so quick to respond and went above and beyond to make things right. I have never had someone take care of us the way she did, her kindness is out of this world. She is a fantastic host and she really made our stay special. Not to mention, the place is extremely cozy and cute, it has everything you need for a nice trip! (and the bed is super comfy best sleep of my life)

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.

Stay near Winter Park's top sights

Orlando Science Center289 locals recommend
Full Sail University26 locals recommend
AdventHealth Orlando25 locals recommend
Orlando Museum of Art215 locals recommend
Harry P. Leu Gardens197 locals recommend
Charles Hosmer Morse Museum of American Art168 locals recommend

Destinations to explore

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