Best 14 Airbnb Vacation Rentals In Winter Park, Florida, The USA - Updated 2021

airbnb Winter Park Florida, Usa

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 soon? Consider staying at one of these great Airbnb vacation rentals in Winter Park, Florida, the USA below.

1. Cozy and convenient vintage home with private bath (from USD 50)

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
Winter Park, Florida, United States
81 reviews
Private room in apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
coffee was also available in the kitchen but enjoy it on her back porch for some fresh air
elizabeth told us how to turn on the ceiling fan which really helped
the bed linens and pillows were perfect for a restful nights sleep
there is a nicely sized private bath kitchen living room
i had a great stay at elizabeth's comfortable apt
a clean and comfortable place to stay
the place was clean and comfortable
the condo unit was spotless clean
clean cozy room- very comfortable stay
elizabeth provides a clean comfortable and convenient room
it felt like home and she was a great host
great host would return :)
beautiful host and a wonderful home
elizabeth was a wonderful host
elizabeth was a great host
great location for winter park touring
close to great restaurants and shops
this was a great location and very affordable
it is a nice walk from here into the heart of winter park
it is comfortable safe and close to winter park
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2. Comfy room in Winter Park home (from USD 35)

This cozy bedroom with a private bathroom is located north of historic Park Ave Winter Park, Full Sail college, UCF, Rollins college and downtown Orlando. The bathroom is shared when the other room is occupied. Other amenities include cable TV, WIFI, kitchen, iron, hanger, and free parking.

For Ladies Only Cozy and Comfy Room, Winter Park
Winter Park, Florida, United States
106 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the mattress on the bed was fantastic- soft but supportive
our room was comfortable and just as described
the bed was super comfortable and the room was perfect and just as described
the room was perfect - very quiet table for working space comfortable bed
we had a great night's sleep and a hot shower
very clean house
clean house :)
clean accomodating and very peaceful
super clean quiet and very relaxing
song s house was very clean and quite
she is a wonderful host
she is a lovely host
song was a very respectful host
song was the best host
she is a superb host
very safe to walk in
wonderful easy location just ten minutes from rollins
nice location by a target malls and winter park
song’s place is a cozy cute well located place for ladies
very safe location and easy to communicate with
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3. Private room in a house (from USD 30)

Sueli’s place has an amazing private room, shared bath, and access to the living room, kitchen, and a full refrigerator. The room is one of the rooms in a home that is situated in a quiet residential neighbourhood. The bedroom is nice with a comfortable bed, soft and firm pillows, TV and a clean bathroom. The accommodation has its own private entrance with a key for late night entry. Other amenities include WIFI, kitchen, dryer, and free parking. It is located at an easy drive to the downtown area of winter park.

Quarto # 1 New para alugar em Winter Park, FL.
Winter Park, Florida, United States
87 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the space is sparkling clean the bed is very comfortable and the amenities are great
i would definitely recommend sueli's place as it's a very comfortable place to stay
nice clean smelled great
clean and exactly as described
clean comfortable and affordable
the house was clean and comfortable
the place is super clean and organized
they were great host
she is a great host and very kind
sueli is a great host
sueli was a great host
our host was fabulous to accommodate us & meet us on our arrival
quiet and easy to park if you drive to orlando
it was an easy drive to the downtown area of winter park
my stay at sueli's place was great
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4. Private room in Olde Winter Park (from USD 70)

This private room is on the third floor and is equipped with a bed and a bath. The space is clean, well maintained and homey. You have a separate entrance, a mini kitchen and your own bathroom. Other amenities include TV, WIFI, friendly laptop working space, hanger, and dryer. The location is close to Rollins College and the shops and dining of Park Avenue and other walkable bars and restaurants.

Old WP-Walk2restaur-book mo but stay less-WP Code
Winter Park, Florida, United States
118 reviews
Private room in apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
fabulous space and furniture loved the mini- apartment feel to it
i liked the kitchenette and the balcony overlooking the tennis court during breakfast
a charming space like a small apartment
hair drier and iron was also available a great host curtis responds rapidly to all texts
the room was very private and there was a beautiful terrace to sit out on
clean and well kept
room is clean and well equipped
the space itself is clean well maintained and homey
it is clean quite and in a safe neighborhood
the room was comfortable and clean and was priced perfectly
great host and very personable
the host was friendly and warm upon arrival
curt is a wonderful host
amazing host amazing space tremendous value
he was a great host and provided a lot of input on restaurant locations
safe neighborhood and amazing location
great location and great value
downtown winter park is about a mile away so perfect location
great location i can not stress that enough
great location walking distance from all that winter park has to offer close to downtown orlando
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5. A fully furnished studio nestled in a verdant garden (from USD 78)

Enjoy the ultimate staycation as you spend your lazy days at this fully furnished studio that boasts a verdant garden that will please your eyes for as long as you stay. Wake up to the tranquil atmosphere in the morning and sleep in the quiet of the night. There are plenty of large windows to guarantee you get enough natural sunlight. The suite is equipped with one bedroom, along with one bathroom, a kitchenette, and spacious living and entertainment areas.

Atmospheric Studio in the Garden
Winter Park, Florida, United States
225 reviews
Entire guest suite 1 Bed 0 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
great space ac blows soo cold bed is comfy with a kitchen
the various amenities and tiny details that they have added make it both pretty and comfortable
if you are into tv there is a nice one well positioned above the couch (and the bed)
this is an adorable well decorated space with the most comfortable mattress ever
we were so comfortable and the space felt so private
it was clean and comfortable
very nice and clean and comfortable
the space is clean cute and homey
this place is very clean and comfortable
great place clean and awesome atmosphere
justin is responsive and offered great hospitality
the hosts were gracious and communicative
justin was a great host responding very quickly to any queries
he was also a flexible host and communicated with us so wonderfully
the stay was amazing the host justin had great hospitality and made sure that our stay was going great
perfect location to discover winter park
the location spots with my favorite restaurants where all near by
location was great in a quiet safe neighbourhood only 30 minute drive from theme parks
a very nice studio located in a quiet neighborhood
nice neighborhood convenient location private and quiet
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6. A modern condo in the heart of Winter Park (from USD 105)

Feel like home as you stay at this modern condo that will serve as your urban oasis, right in the heart of famous Winter Park. Featuring two spacious bedrooms and two bathrooms, the modern condo is superb for four people. Take a relaxing soak in the heated pool or the hot tub after spending a day exploring the best attractions in the city. In the evening, enjoy a barbecue party in the outdoor area that features an outdoor grill.

Apt D -Modern Elegance in the Heart of Winter Park
Winter Park, Florida, United States
200 reviews
Entire apartment 2 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
very comfortable with lots of extra(helpful) amenities
i appreciate the thoughfulness of leaving some muffins oj coffee for breakfast
comfy beds lovely decor nice view of the pool on one side and balcony on the front
very comfortable nicely decorated great location chris has all the amenities you would ever need
want to relax? just take a dip in the pool
everything was very clean and modern
very nice clean apartment
this apartment is clean and delightful
very clean and thoughtful touches throughout
great place to stay very clean and comfortable
christopher is a wonderful host
christopher was a delightful host
christopher is an amazing host and the apt is decorated thoughtfully
beautiful place great host i definitely will be returning soon
" everyone we met was welcoming and friendly and the towns attractions are first rate
fantastic location for downtown winter park
beautiful condo in a great location
and the location is excellent
perfect location near winter park village
easy walking distance to downtown park avenue
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7. Tastefully designed bungalow in trendy neighborhood (from USD 73)

Experience a pleasant stay in Florida when you choose to stay in this stylish, recently renovated 1920s bungalow in Orlando’s trendier neighborhoods. This property is situated in the city center and is just walking distance to the Sun Rail. This bungalow is bright and airy and has a queen bed where guests of two, ideally couples will have a good sleep on. There is also a kitchenette with an oven, stove, microwave, and cookware for guests who prefer to cook some meals indoors. The bathroom is functional with shower essentials and toiletries provided. Enjoy the outdoor patio with market lights which come on at dusk. A breakfast nook is available for guests to enjoy having their morning coffee.

The Shed in Downtown Orlando
Orlando, Florida, United States
335 reviews
Entire guesthouse 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the place has a cozy vibe with natural light and positive energy
having the smart tv where i could sign into my apps was perfect
loved the barn door and well-appointed kitchen
everything was very clean and very aesthetically pleasing
beautiful space very clean and rosy was super friendly
super clean accessible great communication and a place you’ll actually truly enjoy
place is beautiful and clean
a great overnight stay clean cute and cozy
rosy was a wonderful host
rosy was a great host
i highly recommended this host and space
rosy was very communicative and a pleasant host
rosy is such a friendly host
the location was so fitting and close to many local attractions
perfect location and space
fantastic place with great location
great location close to downtown and the college park / ivanhoe area
very safe feeling and close to downtown college park and adorable winter park
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8. Stunning, newly renovated apartment (from USD 79)

Take a few days or a long weekend to experience the best of what downtown Orlando has to offer and stay in this newly renovated one-bedroom apartment. This apartment has a charming lounge area with a flat-screen TV, a dining table, and a kitchen where guests can prepare meals with updated cookware and appliances. Guests of two will be sleeping on a cozy queen bed with plush pillows and high-quality linens. This bright and airy apartment has everything you will need. The full bathroom comes with hot water and toiletries provided for guests to use. Other amenities include WIFI access, laundry facilities, air conditioning, heating, as well as a garden backyard for guests to make use of.

"Park Bungalow" in Downtown Orlando
Orlando, Florida, United States
73 reviews
Entire guesthouse 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
very clean and very comfortable
it was clean quiet and comfortable
very clean and comfortable would definitely stay again
super safe neighborhood great communication with the hosts and amazing amenities
great place to stay for a couple on vacation
Read more reviews

9. Spacious & cozy room in Winter Park home

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!

For Ladies Only Spacious & Cozy Room, Winter Park
Winter Park, Florida, United States
103 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
song was in the process of having an overhead fan installed
she had bottled water available in the room upon arrival and a ceiling fan running
the bedroom is huge and the bathroom has excellent water pressure
the photo of the room is exactly what the room looks like
comfortable room for a good nights sleep
very clean and welcoming
both the room and the bathroom were very clean with clean sheets and towels
everything was very clean and the room was very private
the house was clean and organized
the room was specious clean and comfortable
song was a wonderful host
she is a wonderful host
she is a wonderful host
she is a great host
song was a gracious host
great location to full sail university plenty of shops and restaurants close by
lovely place close to the airport and universal studios
this house is located in the beautiful winter park and only minutes from downtown
very nice place good location
location is great for winter park or the general orlando area
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10. Private room in a secure neighbourhood

This home is in a secure neighbourhood equipped with a kitchen, bathroom and new furniture. The bedroom has a new queen size NEST Bed with NEST pillows. The bedroom has a 27’’ Samsung TV, closet space, dresser, and nightstand. The shared spaces include the dining room area, kitchen for storing items in the fridge, cabinets and pots/pans for light cooking. You can also access the guest bathroom and backyard grill area. The accommodation also has WIFI and free parking. Winter Park/Park Ave & Rollins College are all within 5 minutes travelling distance by car.

41 reviews
Private room 1 Bed

11. Shared room in a house, Twin I and II

Twin I and II is a shared sleeping space in the house, meant for a single traveller who is open to sharing with another. The room has two twin size beds, individual bedside tables, lamps, and a remodelled shower room. The guest has access to the large yard with fire pit and sitting, a laundry room and a kitchen for cooking needs. Other amenities include WIFI, hanger, iron, and dryer. The House on Royal Palm is located just a few minutes’ drive to downtown Orlando, and a short walk away from Milk District, Audubon Park Garden District, and Mills 50.

Twin II- $25 all inclusive/open pantry
39 reviews
Shared room 1 Bed

12. Guest room near downtown and Florida Hospital

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
Winter Park, Florida, United States
208 reviews
Private room in bungalow 1 Bed 1 Bedroom 1 Bathroom

13. Family home near all attractions

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.

Orlando, Florida, United States
231 reviews
Entire house 5 Beds 4 Bedrooms 1 Bathrooms
Top guest reviews
Amenities & Room:
nice large kitchen gas grill good internet and television channels
enjoyed our coffee and breakfast on the back patio in the mornings
there were 7 of us total and we slept comfortably in the 5 queen beds
gas grill was available too the house is roomy and comfortable
the beds were comfy the neighborhood was safe and the pool was amazing
also it was very clean and well stocked
it was super clean and welcoming
the house was clean and the pool was great
the space was very clean and the property well-kept
everything was extremely clean and the beds were extremely comfortable
thank you to the hosts
they said it was very nice and the host was great with communicating
the host is very accommodating and easy to reach if anything is needed
great unit and awesome host you’ll love it
host was a good communicator and overall a good value
location is a quick drive to many attractions
the location was perfect
nice location 15-20 minute drive to international dr
the airport is also very close an easy 15 min drive
the location was great for going to city walk saturday night
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14. Charming guest house in Winter Park

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
Winter Park, Florida, United States
292 reviews
Entire guesthouse 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
and even popped right over when i asked for an iron and then for stronger coffee and milk
this cottage is so perfect for a couple it was super cozy the bed was very comfortable
the bed is comfy the complimentary tea and coffee are great and the location is perfect
it had everything we needed and was very comfortable
what a true delight the guesthouse immediately felt comfortable upon arriving
super clean and comfortable
very clean and well appointed
a clean comfortable stay
bath is very clean and easy to maneuver
beautiful guest house that was comfortable and clean with specialthoughtful touches
the hosts are eager to please and helpful answering questions
joyce was a wonderful host
the hosts were the best their friendly and casual manner was perfect
the hosts are so friendly and accommodating
they were very responsive when i texted questions before and during our stay
comfy bed and a great location
the location is perfect for the visitor to winter park
great restaurants wine lakes museums are all within walking distance
the location was so close to everything and the beautiful property was quiet and peaceful
this little cottage was ideal for our short stay in winter park
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A nature lover's paradise

With more than 70 parks and multiple events, festivals, and celebrations throughout the year, Winter Park is a visitors’ delight. The art and culture-filled city offer a wide range of attractions for people of all age groups. It is a must see-destination in Florida.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Journalist and a freelance writer based in India, traveling for K.Venkateshwar.Rao means exploring the world in search of arts and culture, interesting people, great food, and hidden gems. He has...Read more

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