Holiday rentals in Winter Park
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Winter Park
Guests agree: these stays are highly rated for location, cleanliness, and more.
Guest favourite
Flat in Winter Park
Get a Little Glam in a Retro Palm Beach-Style Boudoir
The whole upstairs portion of the building is all yours. Location is prime as it is close to all things wonderful in Winter Park FL. Two streets behind is Lake Killarney. The space is beautifully decorated and offers guests a charming get away.
Please note: It is a 13.6 mile drive (21 - 40 minutes depending on traffic) from Universal Studio's and a 21.7mile drive (24 - 45 minutes depending on traffic) to Disney World.
There is a lock box located under the stairwell on the left side of the building. I will message you with your code for access. Once you get your key, head on up the stairs and enjoy your home away from home. Welcome!
I live 3 minutes away from the Air BnB property and I work in the downstairs portion of the building, so I am local and available to assist with any additional requests. Message me anytime! Or text 407 575 3502
The Fairbanks corridor of Winter Park is the main artery to affluent areas, offering great shopping and dining close by. This hidden gem is a short walk to grocery stores, restaurants, and Winter Park Village shopping district with its movie theater.
Light sleepers, please be aware that there is the potential for traffic noise.
The BnB offers a large parking lot. You should have no problem at all if you desire to arrive by car. The area is also safe to bike around and Uber or Lyft operates in the area.
No smoking please.
22–29 DecIndividual Host,
£114 per night
4.95 out of 5 average rating, 280 reviews
Guest favourite
Townhouse in Winter Park
Beautiful Downtown Winter Park
WP requires rentals to be listed as 28 days. For alternate rentals please contact me with dates requested.
A 1 bedroom New England style townhouse. Enjoy brick streets, old oaks and lake access all within a 5 minute walk to downtown Winter Park, home of nationally known art festivals and museums, Saturday farmers market, Rollins College and many fine dining establishments. Pick herbs from our garden to use in cooking. Lounge on your private deck to the relaxing waterfall sounds of our koi pond.
15–22 JunIndividual Host,
£123 per night
4.98 out of 5 average rating, 193 reviews
Guest favourite
Bungalow in Winter Park
Cozy 2/2 Bungalow - Downtown Winterpark/Orlando
Your family will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, you will be 5 minutes from Downtown Orlando and Downtown Edgewater, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! College Park local parks and golf course within walking distance!
Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music
16–23 AugIndividual Host,
£144 per night
4.98 out of 5 average rating, 222 reviews
Holiday rentals for every style
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Quick stats about holiday rentals in Winter Park
Total rentals | 410 properties |
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Rentals with dedicated workspaces | 240 properties have a dedicated workspace |
Rentals with a pool | 100 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 | 17K reviews |
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