
Monthly Rentals in Lake Osceola
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 reviewsCharming 2/1 Condo on a Lake in Winter Park
LindaRating, 5 stars13 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!
Superhost

Guesthouse in Winter Park
4.95 out of 5 average rating, 55 reviewsWinter Park City 32789 Mile to Park Ave & Rollins
ClarkeRating, 5 stars3 months ago
Georgiana and Adrian’s space has been a fantastic place to stay over the past several months. The space is as described as well as the convenience and area in which it is in. Winter Park has a lot to offer in terms of places to go and things to do. As for the space, the updated finishes makes it feel like a hotel room. There is a great mutual respect for privacy while at the same time immediate responsiveness should something be needed. Highly recommended.
Superhost

Apartment in Winter Park
5 out of 5 average rating, 15 reviewsBarbour House 300 with King Size Bed
StephanieRating, 5 stars1 month ago
We stayed at Barbour House for 3 months. It was the perfect stay. The garden and landscaping were lush and inviting--resort like. The apartment was exactly as pictured, light and airy, and the kitchen and bath were modern. A few times I had questions and once the toilet broke. Richard texted within minutes and the problem was addressed within an hour. Richard was on the grounds frequently and he always wanted to know if everything was okay. For those who may not know, Barbour House is located in an exclusive area of Winter Park and Park Ave shops and restaurants are one block away. We hope to return next winter.
Guest favorite

Apartment in Winter Park
4.95 out of 5 average rating, 292 reviewsRetro Palm Beach-Style Boudoir
AlexandraRating, 5 stars3 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)
The comforts of home and great monthly rates
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
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*Some exclusions may apply in certain geographies and for some properties.