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
4.92 out of 5 average rating, 159 reviewsPrivate Backyard Cottage in Mills50
Aug 13 – 20
Guest suite in Orlando
4.93 out of 5 average rating, 559 reviewsCharming Comfortable Cottage in College Park
Nov 30 – Dec 7
Guesthouse in Maitland
4.98 out of 5 average rating, 114 reviewsPrivate 1-bd Mid-Century Guesthouse
Dec 10 – 17
Guesthouse in Orlando
4.95 out of 5 average rating, 130 reviewsJefferson St. Cottage
Jul 15 – 22
Guesthouse in Orlando
4.89 out of 5 average rating, 604 reviewsThornton Park's Historic Guest House - private
Aug 8 – 15
Yurt in Orlando
4.96 out of 5 average rating, 216 reviewsLakefront Yurt King Bed *A/C* Kayaks, Bikes
May 5 – 12
Guesthouse in Orlando
4.83 out of 5 average rating, 196 reviewsLovely Spacious Guesthouse in Mills 50 District
Nov 25 – Dec 2
Loft in Orlando
4.86 out of 5 average rating, 1096 reviewsDowntown (Ivanhoe Village) Loft Apartment
Aug 26 – Sep 2
Other great vacation rentals in Winter Park
Home in Orlando
4.9 out of 5 average rating, 176 reviewsDowntown Orlando-Harwood House-Lake Eola-Historic
Jul 29 – Aug 5
Condo in Winter Park
4.81 out of 5 average rating, 57 reviewsLovely Winter Park Home close to Hospitals !
Jan 7 – 14
Guesthouse in Orlando
4.95 out of 5 average rating, 38 reviewsNew Mid Century-Modern Studio
Jul 8 – 15
Bungalow in Winter Park
4.87 out of 5 average rating, 63 reviewsCharming Farmhouse Bungalow
Oct 24 – 31
Apartment in Winter Park
4.88 out of 5 average rating, 32 reviewsThe Lake House
Mar 19 – 26
Bungalow in Orlando
5.0 out of 5 average rating, 23 reviewsCozy Cottage in College Park.
Feb 27 – Mar 6
Tiny home in Winter Park
4.89 out of 5 average rating, 18 reviewsComfy Tiny Home @WP. Large Private Deck+Queen bed
Sep 30 – Oct 7
Guesthouse in Orlando
4.93 out of 5 average rating, 44 reviewsAmazing place in exclusive area Downtown Orlando
Sep 24 – Oct 1
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 1,500 vacation rentals in North Orange, over 1,050 vacation rentals in Lake Formosa, and over 1,990 vacation rentals in Baldwin Park.
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 bungalow rentals in Winter Park?
Experience the best of Winter Park with our bungalow 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 apartment rentals in Winter Park have a gym?
Absolutely! We offer over 20 apartment 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 apartment rentals in Winter Park have wifi?
Absolutely! We offer over 80 apartment rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.
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