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 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
5 out of 5 average rating, 3 reviews

Private Guest Suite by Park Ave & Rollins

MargaritaRating, 5 stars1 month ago
I really enjoyed my stay here. It is private and surrounded by a lovely garden. Nicholas was friendly and helped with any requests. I really liked sitting out on the terrace and looking at all the surrounding greenery. The place is well-equipped with everything you need and the interior is really nice, too. Would stay here again!
Top guest favorite
Townhouse in Orlando
5 out of 5 average rating, 24 reviews

Cozy Duplex in Orlando's Heart

AllisonRating, 5 stars1 week ago
I can’t say enough about our 30 day stay! It was a dream come true for us! We came to see our grandchildren and it was the perfect location. Street is peaceful and safe. Walked the dog at night without a care. Close to all the fun and food in downtown and Milk district. We are booked to come again for 2 weeks in July! Don’t hesitate to stay here!!
Guest favorite
Apartment in Orlando
4.9 out of 5 average rating, 31 reviews

Lakefront Apt near Leu Gardens and Winter Park

LuminitaRating, 5 stars2 weeks ago
I absolutely loved staying at Wendy’s place. The lake view is astonishing and waking up every day to that was a treat. The neighborhood is very peaceful and close to lots of nice places in Orlando. I would def recommend this place to anyone looking for accommodation in Orlando.

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
Orlando Museum of Art215 locals recommend
Harry P. Leu Gardens197 locals recommend
Scenic Boat Tour160 locals recommend
Prato124 locals recommend
East End Market111 locals recommend

Destinations to explore

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