Monthly Rentals in Lake Osceola

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

Nearby monthly rentals

Superhost

Guest house in Winter Park

4.95 out of 5 average rating, 56 reviews

Winter Park City 32789 Mile to Park Ave & Rollins

ClarkeRating, 5 stars4 months ago

As always a great stay. Please read my previous reviews which provide finer details. I recommend staying at this location to anyone.

Guest favourite

Home in Orlando

4.96 out of 5 average rating, 27 reviews

Uptown Orlando Cozy 1/1 Home Near Medical District

KennethRating, 5 stars5 months ago

Great place with only a short drive to many hotspots and good spots to eat.

Superhost

Flat in Winter Park

5 out of 5 average rating, 28 reviews

Mid-Century Luxury Directly off Park Ave (2nd flr)

SandraRating, 5 stars3 months ago

This apartment is very comfortable, nice, well appointed, clean and a great location for Winter Park. The kitchen is very well equipped - probably the best we've ever stayed in. The bathroom is small but very serviceable and well stocked. The neighborhood is quiet, yet close to Park Ave. We enjoyed our stay and will defihitely consider staying here again.

Guest favourite

Flat in Winter Park

4.96 out of 5 average rating, 113 reviews

Historic Architecturally Distinctive Apartment 520

MatthewRating, 5 stars2 weeks ago

Great place, beautiful area. The Richard is definitely proactive and helped us with all our needs 👍👍.

Explore all

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments, these furnished rentals have all the amenities of home.

Digital nomads & travelling professionals

Comfortable accommodation for nomadic and remote working professionals with wifi and dedicated work spaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets so that you can bring your four-legged friend along.

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 holiday 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

Travelling 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

Kitchen

Wifi

Pet-friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Destinations to explore

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