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
4.95 out of 5 average rating, 133 reviewsJefferson St. Cottage
Guesthouse in Orlando
4.98 out of 5 average rating, 149 reviewsThe Loft in College Park
Guesthouse in Orlando
4.91 out of 5 average rating, 146 reviews8th Green Cottage - A relaxing oasis in the city
Guesthouse in Winter Park
4.93 out of 5 average rating, 267 reviewsTiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 386 reviewsGuest Suite! Key West in Altamonte Springs!
Villa in Winter Park
4.84 out of 5 average rating, 109 reviewsLuxury Villa, 3bed/2bath Great Location with Pool
Loft in Orlando
4.92 out of 5 average rating, 774 reviewsUPSCALE LOFT SPACE CLOSE TO DOWNTOWN.
Home in Orlando
4.9 out of 5 average rating, 184 reviewsCozy Milk District Home | Downtown | Free Parking
Other great vacation rentals in Winter Park
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 318 reviewsSt. Augustine suite
Home in Orlando
4.91 out of 5 average rating, 179 reviewsDowntown Orlando-Harwood House-Lake Eola-Historic
Guesthouse in Orlando
4.96 out of 5 average rating, 490 reviewsPrivate Luxurious Apt. - Historic Downtown Orlando
Home in Winter Park
4.97 out of 5 average rating, 106 reviewsRelax on a private lake in Winter Park!
Guest suite in Orlando
4.93 out of 5 average rating, 148 reviewsGuesthouse in Mills 50 w backyard walking to bars
Guesthouse in Orlando
5.0 out of 5 average rating, 162 reviewsTreehouse Inn Downtown Orlando, 2 bedrooms 2 bath
Tiny home in Orlando
4.94 out of 5 average rating, 155 reviewsSunset Lakefront View King Bed, Free Bikes Kayaks
Apartment in Maitland
4.81 out of 5 average rating, 191 reviewsAt Mine | Spacious Double Suite in Orlando
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 1,990 vacation rentals in Baldwin Park, over 1,500 vacation rentals in North Orange, and over 1,050 vacation rentals in Lake Formosa.
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 townhouse rentals in Winter Park?
Experience the best of Winter Park with our townhouse rentals, starting at about $30 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 house rentals in Winter Park have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Winter Park have self check-in?
Absolutely! We offer over 10 condo rentals with self check-in in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Park have wifi?
Absolutely! We offer over 190 house rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.
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- Rentals with pools Winter Park
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