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, 132 reviewsJefferson St. Cottage
Feb 5 – 12
Guesthouse in Orlando
4.97 out of 5 average rating, 288 reviewsOasis Garden Cottage -cozy, chic, near everything!
Oct 19 – 26
Treehouse in Saint Cloud
4.97 out of 5 average rating, 793 reviewsTreeHouse in the Cloud, (Close toTheme Parks
Apr 14 – 21
Guest suite in Winter Park
4.96 out of 5 average rating, 245 reviewsAtmospheric Studio in the Garden
Jun 15 – 22
Loft in Orlando
4.87 out of 5 average rating, 1104 reviewsDowntown (Ivanhoe Village) Loft Apartment
Aug 9 – 16
Guesthouse in Orlando
4.98 out of 5 average rating, 149 reviewsThe Loft in College Park
Oct 24 – 31
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 385 reviewsGuest Suite! Key West in Altamonte Springs!
Jan 3 – 10
Cottage in Winter Park
4.95 out of 5 average rating, 346 reviewsWinter Park Pearl 6 min drive to historic Park Ave
Jul 2 – 9
Other great vacation rentals in Winter Park
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 317 reviewsSt. Augustine suite
Aug 12 – 19
Home in Orlando
4.95 out of 5 average rating, 100 reviewsTrendy Downtown Orlando Oasis
May 8 – 15
Guesthouse in Orlando
4.84 out of 5 average rating, 201 reviewsLovely Spacious Guesthouse in Mills 50 District
Mar 23 – 30
Guesthouse in Orlando
5.0 out of 5 average rating, 155 reviewsThe Sacred Space Downtown Orlando Milk District
Feb 6 – 13
Home in Winter Park
4.97 out of 5 average rating, 104 reviewsRelax on a private lake in Winter Park!
Feb 3 – 10
Guesthouse in Orlando
5.0 out of 5 average rating, 162 reviewsTreehouse Inn Downtown Orlando, 2 bedrooms 2 bath
Jul 2 – 9
Guest suite in Orlando
4.93 out of 5 average rating, 563 reviewsCharming Comfortable Cottage in College Park
Jun 30 – Jul 7
Yurt in Orlando
4.96 out of 5 average rating, 223 reviewsLakefront Sunset Yurt King Bed *A/C* Kayaks, Bikes
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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