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 reviews

Charming 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 reviews

Winter 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 reviews

Barbour 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 reviews

Retro 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)

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.
*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Park
  6. Lake Osceola
  7. Monthly Rentals