Winter Park vacation rentals
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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
Guest suite in Winter Park
4.83 out of 5 average rating, 103 reviewsModern and Gorgeous Apt Studio 1b1b at Winter Park
Jan 21 – 28
Guest suite in Altamonte Springs
4.97 out of 5 average rating, 300 reviewsSt. Hemingway Suite
Aug 6 – 13
Guesthouse in Orlando
4.96 out of 5 average rating, 488 reviewsPrivate Luxurious Apt. - Historic Downtown Orlando
Oct 1 – 8
Treehouse in Saint Cloud
4.97 out of 5 average rating, 789 reviewsTreeHouse in the Cloud, (Close toTheme Parks
Mar 26 – Apr 2
Yurt in Orlando
4.96 out of 5 average rating, 221 reviewsLakefront Sunset Yurt King Bed *A/C* Kayaks, Bikes
May 27 – Jun 1
Home in Winter Park
4.94 out of 5 average rating, 108 reviewsModern, Quiet & Cozy - Entire house /Winter park
Jun 17 – 24
Guesthouse in Winter Park
4.92 out of 5 average rating, 266 reviewsTiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
Jul 19 – 26
Guesthouse in Orlando
5.0 out of 5 average rating, 152 reviewsThe Sacred Space Downtown Orlando Milk District
Jan 7 – 14
Other great vacation rentals in Winter Park
Home in Orlando
4.9 out of 5 average rating, 178 reviewsCozy Milk District Home | Downtown | Free Parking
Aug 17 – 24
Guest suite in Orlando
4.93 out of 5 average rating, 560 reviewsCharming Comfortable Cottage in College Park
Apr 11 – 18
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 384 reviewsGuest Suite! Key West in Altamonte Springs!
Aug 25 – Sep 1
Apartment in Orlando
4.95 out of 5 average rating, 618 reviewsQuiet Shed in Downtown
Nov 23 – 30
Guesthouse in Orlando
4.89 out of 5 average rating, 608 reviewsThornton Park's Historic Guest House - private
Dec 4 – 11
Condo in Winter Park
4.81 out of 5 average rating, 58 reviewsLovely Winter Park Home close to Hospitals !
Aug 7 – 14
Guesthouse in Orlando
4.95 out of 5 average rating, 40 reviewsNew Mid Century-Modern Studio
Jul 8 – 15
Apartment in Winter Park
4.89 out of 5 average rating, 35 reviewsThe Lake House
Aug 10 – 17
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 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 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 condo rentals in Winter Park have wifi?
Absolutely! We offer over 10 condo rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.
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