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 BathWinter Park, Florida, United StatesTop guest reviews
Amenities & Room:
coffee was also available in the kitchen but enjoy it on her back porch for some fresh airelizabeth told us how to turn on the ceiling fan which really helpedthe bed linens and pillows were perfect for a restful nights sleepthere is a nicely sized private bath kitchen living roomi had a great stay at elizabeth's comfortable aptCleanliness:
a clean and comfortable place to staythe place was clean and comfortablethe condo unit was spotless cleanclean cozy room- very comfortable stayelizabeth provides a clean comfortable and convenient roomHost:
it felt like home and she was a great hostgreat host would return :)beautiful host and a wonderful homeelizabeth was a wonderful hostelizabeth was a great hostRead more reviewsLocation:
great location for winter park touringclose to great restaurants and shopsthis was a great location and very affordableit is a nice walk from here into the heart of winter parkit is comfortable safe and close to winter park
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 ParkWinter Park, Florida, United StatesTop guest reviews
Amenities & Room:
the mattress on the bed was fantastic- soft but supportiveour room was comfortable and just as describedthe bed was super comfortable and the room was perfect and just as describedthe room was perfect - very quiet table for working space comfortable bedwe had a great night's sleep and a hot showerCleanliness:
very clean houseclean house :)clean accomodating and very peacefulsuper clean quiet and very relaxingsong s house was very clean and quiteHost:
she is a wonderful hostshe is a lovely hostsong was a very respectful hostsong was the best hostshe is a superb hostRead more reviewsLocation:
very safe to walk inwonderful easy location just ten minutes from rollinsnice location by a target malls and winter parksong’s place is a cozy cute well located place for ladiesvery safe location and easy to communicate with
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 StatesTop guest reviews
Amenities & Room:
the space is sparkling clean the bed is very comfortable and the amenities are greati would definitely recommend sueli's place as it's a very comfortable place to stayCleanliness:
nice clean smelled greatclean and exactly as describedclean comfortable and affordablethe house was clean and comfortablethe place is super clean and organizedHost:
they were great hostshe is a great host and very kindsueli is a great hostsueli was a great hostour host was fabulous to accommodate us & meet us on our arrivalRead more reviewsLocation:
quiet and easy to park if you drive to orlandoit was an easy drive to the downtown area of winter parkmy stay at sueli's place was great
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 CodeWinter Park, Florida, United StatesTop guest reviews
Amenities & Room:
fabulous space and furniture loved the mini- apartment feel to iti liked the kitchenette and the balcony overlooking the tennis court during breakfasta charming space like a small apartmenthair drier and iron was also available a great host curtis responds rapidly to all textsthe room was very private and there was a beautiful terrace to sit out onCleanliness:
clean and well keptroom is clean and well equippedthe space itself is clean well maintained and homeyit is clean quite and in a safe neighborhoodthe room was comfortable and clean and was priced perfectlyHost:
great host and very personablethe host was friendly and warm upon arrivalcurt is a wonderful hostamazing host amazing space tremendous valuehe was a great host and provided a lot of input on restaurant locationsRead more reviewsLocation:
safe neighborhood and amazing locationgreat location and great valuedowntown winter park is about a mile away so perfect locationgreat location i can not stress that enoughgreat location walking distance from all that winter park has to offer close to downtown orlando
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 GardenWinter Park, Florida, United StatesTop guest reviews
Amenities & Room:
great space ac blows soo cold bed is comfy with a kitchenthe various amenities and tiny details that they have added make it both pretty and comfortableif 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 everwe were so comfortable and the space felt so privateCleanliness:
it was clean and comfortablevery nice and clean and comfortablethe space is clean cute and homeythis place is very clean and comfortablegreat place clean and awesome atmosphereHost:
justin is responsive and offered great hospitalitythe hosts were gracious and communicativejustin was a great host responding very quickly to any querieshe was also a flexible host and communicated with us so wonderfullythe stay was amazing the host justin had great hospitality and made sure that our stay was going greatRead more reviewsLocation:
perfect location to discover winter parkthe location spots with my favorite restaurants where all near bylocation was great in a quiet safe neighbourhood only 30 minute drive from theme parksa very nice studio located in a quiet neighborhoodnice neighborhood convenient location private and quiet
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 ParkWinter Park, Florida, United StatesTop guest reviews
Amenities & Room:
very comfortable with lots of extra(helpful) amenitiesi appreciate the thoughfulness of leaving some muffins oj coffee for breakfastcomfy beds lovely decor nice view of the pool on one side and balcony on the frontvery comfortable nicely decorated great location chris has all the amenities you would ever needwant to relax? just take a dip in the poolCleanliness:
everything was very clean and modernvery nice clean apartmentthis apartment is clean and delightfulvery clean and thoughtful touches throughoutgreat place to stay very clean and comfortableHost:
christopher is a wonderful hostchristopher was a delightful hostchristopher is an amazing host and the apt is decorated thoughtfullybeautiful place great host i definitely will be returning soon" everyone we met was welcoming and friendly and the towns attractions are first rateRead more reviewsLocation:
fantastic location for downtown winter parkbeautiful condo in a great locationand the location is excellentperfect location near winter park villageeasy walking distance to downtown park avenue
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 OrlandoOrlando, Florida, United StatesTop guest reviews
Amenities & Room:
the place has a cozy vibe with natural light and positive energyhaving the smart tv where i could sign into my apps was perfectloved the barn door and well-appointed kitchenCleanliness:
everything was very clean and very aesthetically pleasingbeautiful space very clean and rosy was super friendlysuper clean accessible great communication and a place you’ll actually truly enjoyplace is beautiful and cleana great overnight stay clean cute and cozyHost:
rosy was a wonderful hostrosy was a great hosti highly recommended this host and spacerosy was very communicative and a pleasant hostrosy is such a friendly hostRead more reviewsLocation:
the location was so fitting and close to many local attractionsperfect location and spacefantastic place with great locationgreat location close to downtown and the college park / ivanhoe areavery safe feeling and close to downtown college park and adorable winter park
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 OrlandoOrlando, Florida, United StatesTop guest reviews
Cleanliness:
very clean and very comfortableit was clean quiet and comfortablevery clean and comfortable would definitely stay againHost:
super safe neighborhood great communication with the hosts and amazing amenitiesRead more reviewsLocation:
great place to stay for a couple on vacation
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 ParkWinter Park, Florida, United StatesTop guest reviews
Amenities & Room:
song was in the process of having an overhead fan installedshe had bottled water available in the room upon arrival and a ceiling fan runningthe bedroom is huge and the bathroom has excellent water pressurethe photo of the room is exactly what the room looks likecomfortable room for a good nights sleepCleanliness:
very clean and welcomingboth the room and the bathroom were very clean with clean sheets and towelseverything was very clean and the room was very privatethe house was clean and organizedthe room was specious clean and comfortableHost:
song was a wonderful hostshe is a wonderful hostshe is a wonderful hostshe is a great hostsong was a gracious hostRead more reviewsLocation:
great location to full sail university plenty of shops and restaurants close bylovely place close to the airport and universal studiosthis house is located in the beautiful winter park and only minutes from downtownvery nice place good locationlocation is great for winter park or the general orlando area
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.
#5 LIVE LIKE LOCAL IN WINTER PARK PRIVATE BEDROOM
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
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 HospitalWinter Park, Florida, United States
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.
FAMILY HOME NEAR ALL ATTRACTIONS!Orlando, Florida, United StatesTop guest reviews
Amenities & Room:
nice large kitchen gas grill good internet and television channelsenjoyed our coffee and breakfast on the back patio in the morningsthere were 7 of us total and we slept comfortably in the 5 queen bedsgas grill was available too the house is roomy and comfortablethe beds were comfy the neighborhood was safe and the pool was amazingCleanliness:
also it was very clean and well stockedit was super clean and welcomingthe house was clean and the pool was greatthe space was very clean and the property well-kepteverything was extremely clean and the beds were extremely comfortableHost:
thank you to the hoststhey said it was very nice and the host was great with communicatingthe host is very accommodating and easy to reach if anything is neededgreat unit and awesome host you’ll love ithost was a good communicator and overall a good valueRead more reviewsLocation:
location is a quick drive to many attractionsthe location was perfectnice location 15-20 minute drive to international drthe airport is also very close an easy 15 min drivethe location was great for going to city walk saturday night
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 ParkWinter Park, Florida, United StatesTop guest reviews
Amenities & Room:
and even popped right over when i asked for an iron and then for stronger coffee and milkthis cottage is so perfect for a couple it was super cozy the bed was very comfortablethe bed is comfy the complimentary tea and coffee are great and the location is perfectit had everything we needed and was very comfortablewhat a true delight the guesthouse immediately felt comfortable upon arrivingCleanliness:
super clean and comfortablevery clean and well appointeda clean comfortable staybath is very clean and easy to maneuverbeautiful guest house that was comfortable and clean with specialthoughtful touchesHost:
the hosts are eager to please and helpful answering questionsjoyce was a wonderful hostthe hosts were the best their friendly and casual manner was perfectthe hosts are so friendly and accommodatingthey were very responsive when i texted questions before and during our stayRead more reviewsLocation:
comfy bed and a great locationthe location is perfect for the visitor to winter parkgreat restaurants wine lakes museums are all within walking distancethe location was so close to everything and the beautiful property was quiet and peacefulthis little cottage was ideal for our short stay in winter park
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.
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17 Cheap Airbnbs In Orlando, Florida - Updated 2021Michelle Jamie -
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