Top 10 Airbnb Vacation Rentals In Winter Park, Florida, USA

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Once considered as a winter resort, Winter Park is a nature lover’s paradise with more than 70 parks and is home to various events, festivals, and celebrations throughout the year. From its pretty cobbled lanes, shops and bistros to colourful festivals, and farmers’ markets, Winter Park has emerged as a hot destination for locals and visitors. From the flower boxes, trickling fountains, nature parks, museums to its beautiful homes, Winter Park offers a calm and relaxing experience. The city includes Rollins College and the Charles Hosmer Morse Museum of Natural Art. Not only the city has enough activities to keep you and your family engaged but all the Orlando attractions are just minutes away. Planning a trip to Winter Park? Consider staying at one of these great Airbnb vacation rentals below!
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1. Charming guest house in Winter Park (from USD 69)

AIRBNB
Located at a short drive from downtown Park Ave and Rollins College, this accommodation has a bedroom with two beds and a bath. The lovely apartment has a fridge, microwave and Keurig coffeemaker, cable TV, WIFI, iron, hairdryer and free parking facilities.
Charming Guest House in Winter Park
1 2 3 4 5 165 reviews
ENTIRE HOUSE 2 BEDS 3 GUESTS
USD
69
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 See similar Vacation Rentals in Winter Park  and also compare the prices with Hotels in Winter Park 

2. Family home near all attractions (from USD 130)

AIRBNB
AIRBNB
AIRBNB
This four-bedroom family home has five queen memory foam beds, 1.5 baths, and a fantastic pool. It has everything from a full kitchen, silverware, comfy couch, washer, dryer as well as TV and internet. The courtyard is equipped with a grill to make burgers and steaks and to enjoy a nice meal by the pool. Disney Shopping, Seaworld, Fl Mall are all within a walking distance from the accommodation.
FAMILY HOME NEAR ALL ATTRACTIONS!
 Orlando, Florida, United States
1 2 3 4 5 177 reviews
ENTIRE HOUSE 5 BEDS 10 GUESTS 4 BEDROOMS 1 BATHROOMS
USD
130
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 See similar Vacation Rentals in Winter Park  and also compare the prices with Hotels in Winter Park 

3. Guest room near downtown and Florida Hospital (from USD 26)

This guest room is in a Mid-century styled bungalow with a bedroom equipped with a full sized bed as well as a dresser. The hall bathroom is shared. The kitchen has a microwave, toaster oven, stove top, coffee maker and coffee is included. Other amenities include WIFI, hair dryer, iron, and free parking. Do note that there is no TV in the accommodation.
Guest room near i4, downtown, and Florida Hospital
1 2 3 4 5 96 reviews
PRIVATE ROOM 1 BED 2 GUESTS
USD
26
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 See similar Vacation Rentals in Winter Park  and also compare the prices with Hotels in Winter Park 

4. Spacious & cozy room in Winter Park home (from USD 45)

AIRBNB
AIRBNB
This clean and quiet home is situated just north of historic Winter Park, Park Ave, and downtown. The private bedroom with a private bathroom is near the lobby. Other amenities include laptop-friendly workspace, kitchen, WIFI, iron, hanger, and free parking. Ms Song is a wonderful hostess. She is pleasant, welcoming and sweet. Your stay here will definitely be enjoyable!
Spacious & Cozy room in Winter Park home
1 2 3 4 5 62 reviews
PRIVATE ROOM 1 BED 2 GUESTS
USD
45
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 See similar Vacation Rentals in Winter Park  and also compare the prices with Hotels in Winter Park 

5. Cozy & convenient vintage home with private bath (from USD 35)

AIRBNB
AIRBNB
This is a wonderful room in a lovely condo equipped with a queen size bed, desk, closet space, and a private bathroom. High-speed Wi-Fi and numerous outlets for charging devices are available. The accommodation has a lovely, private patio area for morning coffee. The host offers light breakfast items such as toast, peanut butter, coffee, jam, fruit, etc. Other amenities include kitchen, free parking, iron, hanger, towels and some basic toiletries. Located 15 minutes by foot from downtown Winter Park and only steps away from the Mead Botanical Garden, the apartment is easily accessible to shops, restaurants, and public transportation like trains and buses.
Cozy & Convenient Vintage Home with Private Bath
1 2 3 4 5 52 reviews
PRIVATE ROOM 1 BED 2 GUESTS
USD
35
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