Winter Park vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winter Park
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Park vacation rentals
Other great vacation rentals in Winter Park
Guesthouse in Orlando
4.93 out of 5 average rating, 163 reviewsPrivate Backyard Cottage in Mills50
Guest suite in Orlando
4.96 out of 5 average rating, 245 reviewsUnique Place! East End Market! Baldwin/Winter Park
Guesthouse in Orlando
4.91 out of 5 average rating, 148 reviews8th Green Cottage - A relaxing oasis in the city
Guest suite in Orlando
4.98 out of 5 average rating, 307 reviewsA SUITE RETREAT with a Garden View in the City
Loft in Orlando
4.86 out of 5 average rating, 1112 reviewsDowntown (Ivanhoe Village) Loft Apartment
Treehouse in Saint Cloud
4.97 out of 5 average rating, 807 reviewsTreeHouse in the Cloud, (Close toTheme Parks
Guesthouse in Orlando
5.0 out of 5 average rating, 162 reviewsTreehouse Inn Downtown Orlando, 2 bedrooms 2 bath
Guesthouse in Orlando
4.96 out of 5 average rating, 491 reviewsPrivate Luxurious Apt. - Historic Downtown Orlando
Other great vacation rentals in Winter Park
Guest suite in Orlando
4.93 out of 5 average rating, 563 reviewsCharming Comfortable Cottage in College Park
Guest suite in Winter Park
4.81 out of 5 average rating, 105 reviewsModern and Gorgeous Apt Studio 1b1b at Winter Park
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 388 reviewsGuest Suite! Key West in Altamonte Springs!
Home in Orlando
4.91 out of 5 average rating, 184 reviewsDowntown Orlando-Harwood House-Lake Eola-Historic
Townhouse in Orlando
4.95 out of 5 average rating, 145 reviews★Modern DT Home★King Bed☀️Patios✔Long Stays⚡️WiFi★
Loft in Orlando
4.92 out of 5 average rating, 780 reviewsUPSCALE LOFT SPACE CLOSE TO DOWNTOWN.
Apartment in Maitland
4.82 out of 5 average rating, 276 reviewsAt Mine | Elegant Double Suite in North Orlando
Guest suite in Orlando
4.92 out of 5 average rating, 189 reviewsNew Apart. near Full Sail, UCF, Parks Attractions.
Quick stats about vacation rentals in Winter Park
Total rentals
410 properties
Rentals with dedicated workspaces
240 properties have a dedicated workspace
Rentals with a pool
110 properties have a pool
Pet-friendly rentals
140 properties allow pets
Family-friendly rentals
200 properties are a good fit for families
Total number of reviews
18K reviews
Frequently Asked Questions
Where should I stay in Winter Park?
Make yourself at home in Winter Park by choosing from our most frequently booked neighborhoods. We have over 1,050 vacation rentals in Lake Formosa, over 1,990 vacation rentals in Baldwin Park, and over 1,500 vacation rentals in North Orange.
Are there vacation rentals with a dedicated workspace in Winter Park?
Yes! Work meets play with ease at over 240 vacation rentals in Winter Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winter Park?
Four-legged friends are welcome in Winter Park. Choose from more than 140 vacation rentals for guests traveling with pets.
Are there Winter Park vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Winter Park, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Winter Park?
Experience the best of Winter Park with our condo rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Winter Park?
Winter Park has more than 200 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winter Park have a gym?
Absolutely! We offer over 10 house rentals with a gym in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winter Park have a bbq area?
Absolutely! We offer over 20 apartment rentals with a bbq area in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Park have self check-in?
Absolutely! We offer over 60 house rentals with self check-in in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Winter Park have wifi?
Absolutely! We offer over 10 townhouse rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.
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- Rentals with a fireplace Winter Park
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