
Vacation rentals in Winter Park
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Top-rated vacation rentals in Winter Park
Guests agree: these stays 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

Lovely Winter Park Home close to Hospitals !

UPSCALE LOFT SPACE CLOSE TO DOWNTOWN.

Bungalow Near Epic Universe and Downtown Orlando!

Livingston Pool House- In The Heart of Downtown

Guest Suite near Full Sail in Winter Park

Spacious Home with Pool & Hot Tub near Downtown

Lake View from King Bed+Free Bikes+Kayaks+Espresso

Charming 2BR Cottage, Downtown Orlando
Quick stats about vacation rentals in Winter Park
Total rentals
380 properties
Total number of reviews
19K reviews
Family-friendly rentals
180 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
110 properties have a pool
Rentals with dedicated workspaces
210 properties have a dedicated workspace
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 1,540 vacation rentals in North Orange, over 2,010 vacation rentals in Baldwin Park, and over 1,080 vacation rentals in Lake Formosa.
Are there vacation rentals with a dedicated workspace in Winter Park?
Yes! Work meets play with ease at over 210 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 120 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 180 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 30 house 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 40 house rentals with self check-in in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in Winter Park have wifi?
Absolutely! We offer over 20 private suite rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.
Destinations to explore
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- Rentals with lake access Winter Park
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
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- Reunion West
- Walt Disney World Resort Golf
- ChampionsGate Golf Club
- Island H2O Water Park
- Kissimmee Lakefront Park
- Disney's Hollywood Studios
- Blue Spring State Park
- Things to do Winter Park
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