Best 24 Airbnb Vacation Rentals In Winter Park, Florida, USA

Venkateshwar
Contributing Writer
Updated
| 8 min read

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 visitors. Not to mention, there are multiple lakes where you can go on leisurely boat rides, paddleboarding adventures, and lakeside picnics. You can also visit The Charles Hosmer Morse Museum of American Art, where you can find the collection of Louis Comfort Tiffany’s stunning creations. Although the city has enough things to do to keep you and your family engaged, you can also drive to Orlando in minutes and enjoy its many attractions.

Planning a trip soon? Consider staying at one of the best Airbnb vacation rentals in Winter Park, Florida, USA, listed below.

Event to look out for:

  • Winter Park Sidewalk Art Festival: The Winter Park Sidewalk Art Festival, one of the nation's oldest outdoor art events, draws over 250,000 visitors annually. With over 1,000 artists showcasing works in categories like clay, photography, jewelry, and sculpture, the festival offers something for everyone. It also includes food vendors and a Children’s Workshop.

Popular museum in Winter Park:

  • Rollins Museum of Art: Explore a rich collection of European Old Master paintings and American art. With rotating exhibitions and ongoing programs, it offers a cultural experience at both the museum and The Alfond Inn at Rollins.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 25, 2025.

Your options at a glance

Airbnb Vacation Rentals
Best Feature
Price
Bright and colorful home near Park Avenue Bright and colorful interiors from USD 3780
Rental unit with a unique architecture style Garden with outdoor futniture from USD 6300
Mid-century-style bungalow in Olde Winter Park Fenced backyard with grill from USD 3600
Roomy condo in the heart of Winter Park Shared heated pool and hot tub from USD 500
New England-style home with golf course view Garden with koi pond from USD 115
Fully furnished studio nestled in a verdant garden Friendly neighborhood from USD 2303
Stunning, newly renovated apartment Access to a park with walking trail from USD 135
Private room in Olde Winter Park Walk to bars and restaurants from USD 1078
Homey villa with park view Lake access from USD 4485
Retro-themed home with garden Lovely retro-themed decor from USD 3825
Elegant apartment with heated pool Access to a heated outdoor pool from USD 3900
Tastefully designed bungalow in trendy neighborhood Fire pit area in the shared backyard from USD 60
Spacious & cozy room in Winter Park home Cozy, homelike interiors from USD 55
Shared room in a house, Twin I and II Large yard with fire pit from USD 25
Modern apartment studio best suited for couples Stylish, minimal decor from USD 80
Guest room near downtown and Florida Hospital Free parking from USD 29
Charming guest house in Winter Park Keurig coffee maker from USD 69
Quaint guesthouse for two Outdoor grilling area from USD 62
Private room in a house Located in a quiet residential neighborhood from USD 30
Comfy room in Winter Park home Well-equipped kitchen from USD 45
Cozy and convenient vintage home with private bath Light breakfast items provided by the host from USD 50
Spacious, comfy home with a private pool Pool patio with lounging areas from USD 350
Neat and elegant house perfect for large groups Patio with grill and fire table from USD 300
Private room in a secure neighbourhood Lush garden with outdoor kitchen from USD 43

1. Bright and colorful home near Park Avenue (from USD 5220)

Highlights Family Friendly Convenient Location

Stepping inside this rental unit will make you feel like you stepped inside an artwork. There are splashes of color everywhere — on the couches, chairs, rugs, blankets, and more — and several of the decoration elements are so distinct they stand out easily. With all the colors and brightness, this rental unit lights up your mood the moment you’re inside, which is a wonderful start to your vacation.

Additionally, this property is spacious enough to hold more guests if need be — to be more specific, you can bring up to four more guests with you. Together, you can enjoy the artsy environment, comfortable furnishings, and quality appliances inside. This place is also near Park Avenue, which means trendy restaurants and shops are a few minutes away.

Winter Park, Florida, United States

3.74 km (2.4 mi) from Orlando Science Center
25 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Host:
great host amazing home and location
Location:
this condo is the perfect walking location to all the shops of park ave
the ideal location and cool mid century vibe of this place are hard to better in winter park
the condo is in the perfect location in winter park right in the action and minutes from everything
great location the space was in a perfect part of winter park
it is gorgeous and the location could not be any better
Cleanliness:
bathroom was sparkling clean
bathrooms and kitchen all updated and clean felt very comfortable
the place was super fun and full of very clean vintage decor
very clean and comfortable space with lots of little touches and comforts of home
it was so clean gorgeous inside and there isnt a better location in winter park
Read more reviews

2. Rental unit with a unique architecture style (from USD 7605)

Highlights Couple Travel Good Location

Want to stay in a rental unit with an architectural style so unique you can’t take your eyes away when you see it? If yes, then look no further because this property fits the bill.

With its cypress ceiling, custom cabinetry, and French doors, this apartment makes it feel like you’re inside a magical place. It’s also wonderfully furnished, with a spacious living room, charming bedroom, well-stocked kitchen, and beautiful backyard. When you look out the window, you’ll be greeted by the city’s breathtaking scenery.

This apartment is also one block away from Park Avenue, while Disney World and some of Florida’s best beaches are a short drive away. As such, this unit is perfect for solo travelers and couples on their romantic getaway.

Winter Park, Florida, United States

3.83 km (2.4 mi) from Orlando Science Center
114 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
very helpful friendly host who communicated well
richard is a great host that is eager to accommodate your every need
richard is a great host very communicative and has done an amazing job outfitting his home
richard is a super duper host very responsive and accommodating
richard was a gracious and responsive host
Location:
wonderful location — close to park avenue shops and restaurants yet located in a quiet serene neighborhood
wonderful place and great location
great location in a charming historic building
fabulous unit- perfect location to walk to park ave
one minute walk to park ave with great dining and shopping
Cleanliness:
the place was very clean
the place was extremely clean and had everything i needed
lovely stay this place is adorable inside and out so clean and comfortable
everything was light and airy and very clean
great vibe clean and close to some cool restaurants
Amenities & Room:
coffee and breakfast on the patio a nice touch
richard’s place is stylish bright and perhaps my favorite features - a super comfortable couch and bed
beautiful and quaint complex apartment and courtyard
most comfortable bed and linens
fantastic complete home -- fridge laundry sitting room -- perfect for an extended stay
Read more reviews

3. Mid-century-style bungalow in Olde Winter Park (from USD 5073)

Highlights Family Friendly Pet Friendly

This mid-century bungalow, furnished with a modern interior design in mind, is the ideal option for families visiting Winter Park. With three beds (one queen-size and two single beds) inside two bedrooms, this property can hold up to five people. There are other amenities that will make your stay more comfortable, such as two televisions, laundry facilities, free WIFI access, and a fenced backyard. There’s space for you and your kids to have fun.

Moreover, local attractions like Park Avenue and various museums are a short drive away. So, if you and your family want to do more Winter Park exploration, you can do so with ease.

Winter Park, Florida, United States

4.71 km (3.0 mi) from Orlando Science Center
36 reviews   Wifi Available
Entire bungalow 3 Beds 5 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 5

Top guest reviews
Host:
great house great owner
kathy was very responsive and a great host i definitely recommend this house
kathy is great host and was always available to communicate
kathy was also very helpful responsive and easy to communicate with
kathy was also very responsive to our needs
Location:
great location in winter park
wonderful location on very quiet street
wonderful neighborhood for walking
kathy’s place is adorable and located to a lot of resources; wish we could’ve stayed longer
the house was in a great location quiet neighborhood close to shopping restaurants grocery store park ave
Cleanliness:
everything was clean and fresh
also the house was super clean when we arrived
and there are lots of clean linens blankets towels and soft extra pillows
house is small but very clean with nice outside spaces
the house is beautiful clean and the location is perfect
Amenities & Room:
loved the screen room and breakfast room
it has a great layout and is furnished with gorgeous period furniture that was both comfortable and stylish
loved the sun room kathy is great
Read more reviews

4. Roomy condo in the heart of Winter Park (from USD 5611)

Highlights Pet Friendly Work Travel Family Friendly Good Location

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.

Winter Park, Florida, United States

3.45 km (2.2 mi) from Orlando Science Center
232 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Host:
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
Location:
beautiful condo in a great location
fantastic location for downtown winter park
perfect location near winter park village
and the location is excellent
easy walking distance to downtown park avenue
Cleanliness:
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
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
Read more reviews

5. New England-style home with golf course view (from USD 3278)

Highlights View Work Travel Couple Travel Good Location

Located close to Downtown Winter Park, amidst brick streets and old oaks, this townhouse property has a New England theme. The place has a private deck that overlooks a garden with a koi pond. The house meets all basic requirements, including room-darkening shades for those who wish to sleep in and board games for those who prefer to stay indoors with family. There is a dedicated workspace, as well.

The accommodation is close to The Charles Hosmer Morse Museum of American Art and Rollins College. Those who love exploring can go shopping or dining out and enjoy the different festivals that are organized from time to time.

Winter Park, Florida, United States

2.56 km (1.6 mi) from Orlando Science Center
214 reviews   Wifi Available
Entire townhouse 1 Bed 3 Guests 1 Bedroom 2 Bathrooms

Accommodates: 3

Top guest reviews
Host:
the host were very kind and accommodating
rich is a wonderful host
rick and his wife were so accommodating and kind
very helpful and knowledgeable about wp
rick is such a wonderful host
Location:
the location is perfect
perfect location in winter park
the location is great too walking distance to a wonderful lake and winter park downtown
beautiful street close to lake
it’s within walking distance to so many amazing restaurants and cute shops
Cleanliness:
very clean and comfortable
it was spotlessly clean
very clean comfortable and well equipped
perfect place cozy super clean and comfortable
the house was clean and nicely decorated relaxing and welcoming
Amenities & Room:
accommodations were wonderful - good mattress great shower good living space
it is well-furnished and comfortable
we really enjoying in this lovely air bnb perfect location comfortable
this was a lovely comfortable space for our guest to stay in winter park
Read more reviews

6. Fully furnished studio nestled in a verdant garden (from USD 3092)

Highlights Couple Travel View

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.

Winter Park, Florida, United States

1.44 km (0.9 mi) from Orlando Science Center
258 reviews   Airbnb superhost icon Superhost Wifi Available
Entire guest suite 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

7. Stunning, newly renovated apartment (from USD 364)

Highlights Couple Travel Good Location Work Travel

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.

Orlando, Florida, United States

1.09 km (0.7 mi) from Orlando Science Center
248 reviews   Airbnb superhost icon Superhost Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
super safe neighborhood great communication with the hosts and amazing amenities
Location:
great place to stay for a couple on vacation
Cleanliness:
very clean and very comfortable
it was clean quiet and comfortable
very clean and comfortable would definitely stay again
Read more reviews

8. Private room in Olde Winter Park (from USD 2742)

Highlights Good Location Couple Travel

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.

Winter Park, Florida, United States

2.07 km (1.3 mi) from Orlando Science Center
128 reviews   Wifi Available
PRIVATE ROOM IN RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
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
Location:
great location and great value
safe neighborhood and amazing location
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
Cleanliness:
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
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
Read more reviews

9. Homey villa with park view (from USD 5774)

Highlights View Family Friendly Good Location Pet Friendly Work Travel

Located close to downtown, this pet-friendly haven is near Winter Park Farmers’ Market and a stroll away from charming shops and eateries on Park Avenue. The place has a park view and is also a waterfront accommodation. All basic amenities are provided here, including a well-equipped kitchen.

There is both central air conditioning and central heating for your convenience, along with an indoor wood-burning fireplace that adds to the aesthetic. The place has a patio and a fully fenced-back garden where your furry friend can hang out.

Winter Park, Florida, United States

2.74 km (1.7 mi) from Orlando Science Center
35 reviews   Wifi Available
Entire villa 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Host:
friendly owner who knows the area well
thanks again to our hosts
fantastic hosts that went above and beyond to make us as comfortable as possible
Location:
great location and value
we loved the location
lovely location and so close to all you need to see on winter park
we could easily walk into the downtown area of winter park
excellent location walkable to park avenue and restaurants
Cleanliness:
the condo was clean and comfortable
well decorated and super clean rooms
the apartment was clean stylish and comfortable
super clean and spacious and was so easy to check in
ashley and her sisters are to be commended for their very clean rental property
Amenities & Room:
quiet apt and parking was terrific
Read more reviews

10. Retro-themed home with garden (from USD 2927)

Highlights Couple Travel Good Location

This accommodation includes the upstairs portion of a building that is centrally located in Winter Park. Within these adorned walls, you will find amenities such as a well-equipped kitchen, heating, and air conditioning to make your stay comfortable. Your children will also have fun using the children’s books and toys. The owners here can also provide babysitter recommendations if you require them.

The house is a mere stroll away from the serene Lake Killarney. You can visit local grocery stores and restaurants and go shopping at the shopping district in Winter Park Village during your stay here.

Winter Park, Florida, United States

2.32 km (1.5 mi) from Orlando Science Center
292 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
she was very responsive
excellent experience lovely place and a great host this place has everything you may need
jaycelle the host was simply wonderful so responsive and a pleasure to communicate with
highly recommend this beautiful space jaycelle is a thoughtful host who checks in and responds quickly
Location:
this place was super cute and the coziest
the location is very central to orlando attractions & things to do
it is super close to rollins and park ave
super close to anything you might want or need during your stay
jaycelle's place was thoughtfully designed and very comfortable perfect location for winter park
Cleanliness:
very clean and comfortable
beautiful apartment clean and comfortable
the place is incredibly clean and very comfortable
jaycelle was wonderful the place was super cute and very clean - absolutely gorgeous home
wow this apartment was absolutely perfect for our week long stay clean comfortable and calming
Amenities & Room:
the apartment was just a few minutes from the morse museum (all things tiffany-a wonderful experience)
i felt comfortable and on cloud nine the entire stay; there were days i didn’t want to leave
the aesthetic was nice and the place was comfortable and cozy
the bed was super comfortable the kitchen had everything we needed and the living room was cozy
the bed was ultra comfortable (i wanted to take it with me)
Read more reviews

11. Elegant apartment with heated pool (from USD 154)

Highlights Family Friendly Work Travel Pet Friendly

Find the embrace of both convenience and serenity in one of Florida’s best walking communities. This accommodation has beautiful wooden floors, lofty ceilings, and a contemporary décor that puts your mind at ease. There is a heated pool outside the house with a grill and fire pit on the side for spending fun times with your partner.

The house has a dedicated workspace for your use and a hot tub for you to relax in after work. They also provide bikes for you to ride around and explore.

Winter Park, Florida, United States

3.48 km (2.2 mi) from Orlando Science Center
219 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Host:
christopher is a great host
christopher is a great host and made us feel welcomed and comfortable
correspondence with owner - great
christopher was a great host and the airbnb was perfect would love to stay here again
chris is so responsive and is a great host
Location:
good winter park location
convenient location to nice restaurants and it’s close to disney world
location offers good access to both park ave and winter park village
within walking distance of some great shopping and a fun downtown eating area
outstanding shopping and multiple restaurants nearby both in walking distance and under a five minute drive
Cleanliness:
it was very clean and quiet
amazing place to stay clean and well done
beds very comfy condo extremely clean and appointed
exactly as pictured super clean tastefully decorated
christopher’s place is a stylish extremely clean relaxing place
Amenities & Room:
we also appreciated the bathroom amenities as we forgot to pack ours
they are immaculately clean nicely decorated with all the appliances and amenities one needs for a comfortable stay
chris was easy to work with we felt very welcome in this apartment
Read more reviews

12. Tastefully designed bungalow in trendy neighborhood (from USD 66)

Highlights Good Location Good Neighborhood Couple Travel Budget Friendly

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.

Orlando, Florida, United States

1.04 km (0.7 mi) from Orlando Science Center
727 reviews   Airbnb superhost icon Superhost Wifi Available
Tiny home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

13. Spacious & cozy room in Winter Park home (from USD 55)

Highlights Budget Friendly Work Travel

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!

Winter Park, Florida, United States

6.46 km (4.1 mi) from Orlando Science Center
125 reviews   Wifi Available
PRIVATE ROOM IN HOME 2 Beds 1 Guest 1 Bedroom 1 Bathroom

Accommodates: 1

Top guest reviews
Host:
she is a great host
she is a wonderful host
she is a wonderful host
song was a wonderful host
song was a gracious host
Location:
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
Cleanliness:
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
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
Read more reviews

14. Shared room in a house, Twin I and II (from USD 25)

Highlights Budget Friendly Good Location

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.


2.26 km (1.5 mi) from Orlando Science Center
39 reviews  
Shared room 1 Bed 1 Guests

15. Modern apartment studio best suited for couples (from USD 80)

Highlights Budget Friendly Couple Travel Good Location

Cozy and modern, this guest suite is the perfect choice for couples who are on their romantic vacation. Firstly, this unit may not be spacious, but it still contains all the amenities that you will need, such as a bedroom, a bathroom, a well-stocked kitchen with a dining area, and free parking (both on premises and on the street).

Secondly, this property is located in the heart of Winter Park, which means that all the attractions are nearby. Want to go on a romantic stroll along Park Avenue or a scenic boat tour around Winter Park? Sure, go on ahead — it will only take about a few minutes.

You can even travel to downtown Orlando and visit world-famous attractions like Disney World if you want since it’s less than 30 minutes away via car. You have so many options for fun if you stay here.

Winter Park, Florida, United States

5.95 km (3.7 mi) from Orlando Science Center
108 reviews   Airbnb superhost icon Superhost Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
host responded quickly and was clear
he is a lovely and attentive host
i enjoyed my stay very homely and safe the host was great
Location:
great location great stay
super cute and cozy and right near where i needed to be i winter park
loved my stay here great location in winter park
great location with plenty of places to eat and see
great space in winter park for 1-2 guests
Cleanliness:
everything was clean the bed was very comfortable
clean modern space with homey touches
the place was modern and clean
the place was well beyond clean
clean comfortable and cozy great stay
Amenities & Room:
comfortable setting very well thought of use of space
Read more reviews

16. Guest room near downtown and Florida Hospital (from USD 29)

Highlights Good Location Budget Friendly

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, and coffee maker, and coffee is included. Other amenities include WIFI, a hair dryer, an iron, and free parking. Do note that there is no TV in the accommodation.

Winter Park, Florida, United States

1.51 km (1.0 mi) from Orlando Science Center
208 reviews  
Private room in bungalow 1 Bed 1 Bedroom 1 Bathroom

17. Charming guest house in Winter Park (from USD 69)

Highlights Budget Friendly Good Location

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.

Winter Park, Florida, United States

2.06 km (1.3 mi) from Orlando Science Center
292 reviews  
Entire guesthouse 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
Read more reviews

18. Quaint guesthouse for two (from USD 62)

Highlights Couple Travel Budget Friendly

This private guesthouse can comfortably accommodate two guests and is perfect for both long- and short-term stays. It has a queen-sized bed with fresh bedsheets to ensure a good night’s rest. A kitchen is available for whipping up simple meals. For a more memorable experience, you can request access to the property’s outdoor grill to enjoy an intimate dinner with your significant other. Laundry facilities are also available upon request for your convenience.


1.48 km (1.0 mi) from Orlando Science Center
266 reviews   Airbnb superhost icon Superhost Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
host were friendly and nice
marie and nick were awesome hosts
marie is such a sweet host who was checking in frequently to make sure our stay was perfect
they were attentive and made sure to ask if i needed anything
easy to check in and host gave clear instructions for check-in/check-out
Location:
location was excellent very close to park ave and downtown
location is also very nice
really cute small place for weekend getaway really close to the downtown area
great location and perfect for a quick trip
the location is very central to downtown winter park and i had an easy time getting around
Cleanliness:
everything is clean and comfortable
very clean very cutely decorated
very clean place for an affordable price
everything was clean and the decor was nice
cute clean nice little touches
Amenities & Room:
the room was like the description states quaint
although a guest house was very comfortable and had a good amount of privacy
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19. Private room in a house (from USD 30)

Highlights Budget Friendly Couple Travel Good Location Good Neighborhood

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.

Winter Park, Florida, United States

7.9 km (5.0 mi) from Orlando Science Center
87 reviews   Wifi Available
Private room in residential home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
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20. Comfy room in Winter Park home (from USD 45)

Highlights Budget Friendly Good Location

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.

Winter Park, Florida, United States

6.85 km (4.3 mi) from Orlando Science Center
106 reviews   Airbnb superhost icon Superhost Wifi Available
Private room in residential home 1 Bed 1 Guest 1 Bedroom 1 Bathroom

Accommodates: 1

Top guest reviews
Host:
she is a lovely host
she is a wonderful host
she is a superb host
song was the best host
song was a very respectful host
Location:
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
Cleanliness:
clean house :)
very clean house
clean accomodating and very peaceful
super clean quiet and very relaxing
song s house was very clean and quite
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
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21. Cozy and convenient vintage home with private bath (from USD 50)

Highlights Couple Travel Budget Friendly Good Location

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.

Winter Park, Florida, United States

1.8 km (1.2 mi) from Orlando Science Center
81 reviews   Wifi Available
PRIVATE ROOM IN RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
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
Location:
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
Cleanliness:
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
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
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22. Spacious, comfy home with a private pool (from USD 350)

Highlights Family Friendly Good Location

If you’re looking for a spacious rental home that can accommodate your large group, then you should check out this particular property. Furnished with all the necessary furniture and appliances, this modern sanctuary features three bedrooms (with four beds all in all — one king-size and three queen-size), three full bathrooms, a family room with a fireplace, a fully equipped kitchen, and a cozy dining room.

Additionally, the house comes with a private pool, which you and your companions can enjoy. It’s also centrally located in Winter Park, so although it’s in a quiet neighborhood, you’re near the wonderful attractions of both Winter Park and Orlando. Sightseeing and exploring will be a breeze if you stay here for your vacation.

Winter Park, Florida, United States

4.98 km (3.1 mi) from Orlando Science Center
60 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Host:
host is very responsive
mohamed is a wonderful host
owner is very responsive and helpful
highly recommend this property and the owner
thank you for hosting us
Location:
great location and value
nice location and private pool
cute neighborhood and proximity to downtown winter park is excellent
quite neighborhood but close enough to downtown if you wish to partake in other activities
such a beautiful home great location & neighborhood
Cleanliness:
very clean and stylish
everything was clean and exceeded expectations
the house is clean and well maintained
house was clean and well organized
amazing stay incredibly clean and accommodating
Amenities & Room:
the a/c was nice and cool and the beds were pretty comfortable
the pool is a nice touch for the florida weather and we used it every day
the pool was clean had floats and lots of patio furniture
we loved our stay at mo’s place the house is great—comfortable bedrooms 3 full baths gorgeous big kitchen
the kitchen was well stocked with everything we needed to make a birthday cake and delicious meals
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23. Neat and elegant house perfect for large groups (from USD 300)

Highlights Family Friendly

Nothing says “neat and elegant” quite like this rental. The interior design follows the simple color scheme of white and brown — with dark accents — and there also seems to be a focus on brightness since lighting is abundant. Because of all this, stepping inside this house feels like a giant hug — so warm and comfortable that you just want to ease yourself right in.

This property is also spacious. There are three bedrooms with six beds — a king-size, queen-size, and four small double beds — so it can host up to nine guests. You can enjoy other amenities as well, such as two full bathrooms, free parking on premises, and a fully equipped kitchen.

In other words, this is the perfect place to stay if you’re traveling with your family or friends or you’re on a business trip with your co-workers.

Winter Park, Florida, United States

4.96 km (3.1 mi) from Orlando Science Center
111 reviews   Wifi Available
ENTIRE HOME 6 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Host:
the owner is very helpful and responds almost immediately to any questions
clara was an amazing host
clara was a wonderful host and very easy to get in touch with
great property and an amazing host i would definitely recommend this property to my friends and family
clara is an excellent host with a beautiful home the pictures do not do this home justice
Location:
the location is excellent
beautiful house in perfect location
location was perfect for us
amazing location for my family's needs
wonderful house on a nice cute side street
Cleanliness:
everything smelled so clean upon entry
it was perfectly clean had lots of clean towels and other toiletries
gorgeous lot clean and decorated beautifully
very clean super organized and beautifully decorated
super clean very comfortable and easy to be in
Amenities & Room:
the most comfortable furniture and bedding ever
the beds were super comfy too
huge tvs in every room
the house is very cozy and homey with a great fenced in yard and patio
the house was great it had everything we needed the couches chairs beds were very comfortable
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24. Private room in a secure neighbourhood (from USD 43)

Highlights Good Neighborhood Couple Travel Budget Friendly

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.


2.73 km (1.7 mi) from Orlando Science Center
41 reviews  
Private room 1 Bed 2 Guests

Explore the charms of Winter Park

With more than 70 parks and multiple events, festivals, and celebrations throughout the year, Winter Park is a visitor’s delight. The art-and-culture-filled city offers a wide range of attractions for people of all age groups. So, visit soon and stay in one of these top Airbnbs in the city!

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
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...View profile

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