Monthly Rentals in Winter Park

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

Nearby monthly rentals

Top guest favorite
Condo in Fraser
4.93 out of 5 average rating, 29 reviews

Hot tubs & pool! Amazing views & free shuttle!

DebraRating, 5 stars2 months ago
This was a perfect place for my husband and I to stay for our month-long ski-vacation!!! The kitchen is well appointed, and we loved the wood burning fireplace. It is so close to the grocery store ( weather pending you could walk down the hill!!). This unit is super close to a couple of our favorite places to eat and drink- Fuego Azteca and Fisher’s. The community center was fabulous too!! Heated outdoor pool and hot tubs. You can easily fit more people in this unit without feeling crammed- great closet space- 2 full bathrooms and my favorite- stacked washer and dryer! You can run a small load everyday day or so!
Superhost
Condo in Winter Park
4.78 out of 5 average rating, 318 reviews

Beautiful Cozy Studio at the Base-Heated Parking

VickieRating, 5 stars3 weeks ago
Shawn was great about answering any questions… quickly responded and helpful. Everything went very smoothly, and we loved being so close to the ski lifts and also transportation into town!
Guest favorite
Apartment in Winter Park
5 out of 5 average rating, 9 reviews

Cozy Winter Park Condo - Heart of Town

WillRating, 5 stars2 weeks ago
We had a great stay at David’s condo. You can’t beat the location. Walking distance to all the restaurants and a 1 minute walk to the free bus to take you to winter park as the next stop. It took us a little bit to find a way into the building but entering from the parking garage was easy and didn’t require another key as some of the outer doors on other floors do.
Top guest favorite
Apartment in Winter Park
4.98 out of 5 average rating, 60 reviews

Fraser Crossing Ski/in Out #3422

GeraldineRating, 5 stars2 weeks ago
Erin Anne went above and beyond to accommodate us and our requests. The accommodation was central to the ski area which was perfect

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

Mountain Grind Coffee & Bistro168 locals recommend
Hernando's Pizza Pub166 locals recommend
The Foundry Cinema & Bowl163 locals recommend
Fraser Tubing Hill130 locals recommend
Pepe Osaka's Fishtaco Tequila Bar & Grill101 locals recommend
Hideaway Park Brewery76 locals recommend

Destinations to explore

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