
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.
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)
Top guest favorite

Guesthouse in Winter Park
5 out of 5 average rating, 19 reviewsBrewer Cottage
HarriRating, 5 stars4 months ago
Beverly and Allen are lovely, welcoming and responsive hosts who will take good care of your stay. They have an extremely well stocked kitchen that provides endless cooking opportunities in this cozy cottage tucked away from the main road. Bedroom is comfortable with plenty of USB ports for charging. Drawers under the bed were really helpful for storage. Bathroom was comfortable. Reclining chair in the living room area was wonderfully relaxing. Outside beautiful plants and trees abound and pool is also available when the weather is warm. For those interested in walking, Windsong North Shore Park and back is a spectacular option. Winter Park itself is one of the nicest places in Orlando area. Charles Hosmer Morse Museum with its extensive Louis Tiffany collection, Rollins College with its Mr. Rogers connection, Park Avenue restaurants and shopping, Central Park concerts and touring the lakes are some of the highlights.
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.*
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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.
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*Some exclusions may apply in certain geographies and for some properties.