Winter Park in Florida is a captivating city within the Sunshine State’s embrace. From strolling along the cobblestone pathways of Park Avenue to learning about the architectural brilliance here by visiting Knowles Memorial Chapel, you can engage in different activities here. Not to mention, there are around 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.
Irrespective of the duration of your visit, you can find vacation rentals that suit your taste and comfort. For a relaxing and enjoyable vacation here, check out the list of best vacation rentals in Winter Park, Florida.
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 April 14, 2024.
1. Spacious villa with park view (from USD 249)
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.
Top guest reviews
Amenities & Room:
quiet apt and parking was terrificCleanliness:
the condo was clean and comfortablewell decorated and super clean roomsthe apartment was clean stylish and comfortablesuper clean and spacious and was so easy to check inashley and her sisters are to be commended for their very clean rental propertyHost:
friendly owner who knows the area wellthanks again to our hostsfantastic hosts that went above and beyond to make us as comfortable as possibleRead more reviewsLocation:
great location and valuewe loved the locationlovely location and so close to all you need to see on winter parkwe could easily walk into the downtown area of winter parkexcellent location walkable to park avenue and restaurants
Superhost
2. Luxurious villa with private pool (from USD 170)
This modern villa is centrally located and is close to popular attractions such as the theme parks, Park Avenue, and Downtown Orlando. The place has a dedicated workspace and a well-equipped kitchen. It also has air conditioning and heating to keep you comfortable in all weather conditions.
The villa has a fully fenced private back garden and a patio where you can relax in the evening. There is a private pool in the backyard for those who love swimming.
Top guest reviews
Amenities & Room:
i appreciated he had included things like coffee sugar spices and laundry detergentthe beds were super comfy and we really enjoyed the poolwe like adriano’s place it has beautiful kitchen & bathroomsgreat place with a poolCleanliness:
very clean and comfortablevery clean and smelled greatvery responsive and a clean placehouse was clean and comfortablegreat stay in a clean comfortable and well appointed homeHost:
the host was responsive and fast to answer our questionsgood job at being the greatest hostgreat stay amazing host responsive to needs and even added a welcoming touchadriano is the perfect host and is very responsivekind responsive and would definitely book againRead more reviewsLocation:
perfect location and beautifully keptlocation was perfect as wellgreat spot very well located in winter park close to restaurant and storeslocation was great and neighborhood is quiethouse was very comfortable and great location
3. Retro-themed home with garden (from USD 128)
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.
Top guest reviews
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 leavethe aesthetic was nice and the place was comfortable and cozythe bed was super comfortable the kitchen had everything we needed and the living room was cozythe bed was ultra comfortable (i wanted to take it with me)Cleanliness:
very clean and comfortablebeautiful apartment clean and comfortablethe place is incredibly clean and very comfortablejaycelle was wonderful the place was super cute and very clean - absolutely gorgeous homewow this apartment was absolutely perfect for our week long stay clean comfortable and calmingHost:
she was very responsiveexcellent experience lovely place and a great host this place has everything you may needjaycelle the host was simply wonderful so responsive and a pleasure to communicate withhighly recommend this beautiful space jaycelle is a thoughtful host who checks in and responds quicklyRead more reviewsLocation:
this place was super cute and the coziestthe location is very central to orlando attractions & things to doit is super close to rollins and park avesuper close to anything you might want or need during your stayjaycelle's place was thoughtfully designed and very comfortable perfect location for winter park
4. Elegant apartment with heated pool (from USD 160)
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.
Top guest reviews
Amenities & Room:
we also appreciated the bathroom amenities as we forgot to pack oursthey are immaculately clean nicely decorated with all the appliances and amenities one needs for a comfortable staychris was easy to work with we felt very welcome in this apartmentCleanliness:
it was very clean and quietamazing place to stay clean and well donebeds very comfy condo extremely clean and appointedexactly as pictured super clean tastefully decoratedchristopher’s place is a stylish extremely clean relaxing placeHost:
christopher is a great hostchristopher is a great host and made us feel welcomed and comfortablecorrespondence with owner - greatchristopher was a great host and the airbnb was perfect would love to stay here againchris is so responsive and is a great hostRead more reviewsLocation:
convenient location to nice restaurants and it’s close to disney worldgood winter park locationlocation offers good access to both park ave and winter park villagewithin walking distance of some great shopping and a fun downtown eating areaoutstanding shopping and multiple restaurants nearby both in walking distance and under a five minute drive
5. New England-style home with golf course view (from USD 115)
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.
Top guest reviews
Amenities & Room:
accommodations were wonderful - good mattress great shower good living spaceit is well-furnished and comfortablewe really enjoying in this lovely air bnb perfect location comfortablethis was a lovely comfortable space for our guest to stay in winter parkCleanliness:
very clean and comfortableit was spotlessly cleanvery clean comfortable and well equippedperfect place cozy super clean and comfortablethe house was clean and nicely decorated relaxing and welcomingHost:
the host were very kind and accommodatingrich is a wonderful hostrick and his wife were so accommodating and kindvery helpful and knowledgeable about wprick is such a wonderful hostRead more reviewsLocation:
the location is perfectperfect location in winter parkthe location is great too walking distance to a wonderful lake and winter park downtownbeautiful street close to lakeit’s within walking distance to so many amazing restaurants and cute shops
6. Spacious house with fenced backyard (from USD 130)
Perfect for a family of five, this single-story house is a short drive from Rollins College. The house has aesthetic flooring, sturdy furniture, and a front-covered porch. You can spend time in the fenced backyard here, which has comfortable lawn furniture. There is a fire pit and a grill that you can use. Landscaping care facilities are given to those who are staying for extended periods.
For those who love exploring, places such as Walt Disney World Resort and Universal Studios Florida Theme Park are close by. You can also go shopping or hiking and biking based on your interests and the duration of your stay.
7. Luxurious home with patio and garden (from USD 144)
Experience staying at this bright, spacious home with a modern kitchen, entertainment bar, and spacious living area where you can relax during your vacation. The house has a luxurious master suite and even a tub to unwind after a long day. There is a patio and a garden with a fire pit, which are ideal for evening entertainment.
8. Old house with mid-century modern design (from USD 140)
This bright and colorful house is set on one of the cobblestoned streets in downtown Winter Park. Located close to Rollins College, the place is ideal for those looking to explore the surrounding region with nearby excellent dining options, shopping options, and bars.
The accommodation has heating and air conditioning to keep you comfortable throughout your stay. There is a parking space available for one vehicle on the property.
9. Pet-friendly rental with fireplace (from USD 168)
Freshly renovated with a luminous and inviting ambiance, this charming cottage beckons you into a realm of ease and coziness, amplifying the joy of your vacation in Winter Park. Located centrally, this place is close to the art festival and everything touristy on Park Avenue. Moreover, you can bring two of your pets along for a fee of 150 USD if they weigh less than 50 pounds (22.68 kilograms).
The place has a well-equipped kitchen, space for parking, and laundry facilities. There is outdoor furniture on the lawn for those who love enjoying the view with their evening coffee.
10. Winter Park Oasis (from USD 152)
Located in a historic neighborhood close to Rollins College, this charming house has all the basic amenities you will require throughout your stay. From a functional kitchen where you can cook your favorite meals to a workspace for those deadlines you cannot avoid, the place will make you feel at home.
The accommodation has parking space for two cars, a garden, and an outdoor play area where your children can have fun. While here, you can dine out at the best restaurants and visit Winter Park Village or Casa Feliz Historic Home Museum, which are close by.
Explore the elegance of Winter Park, Florida
Take a break and explore the historic charm and modern vibrancy of Winter Park. This captivating town offers a picturesque backdrop for leisurely strolls and memorable moments. Make your vacation more comfortable by choosing to stay at one of the finest vacation rentals in the area.
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