Holiday Rentals in Winter Park, FL

This private downstairs flat in Winter Park, Florida, is located in a tranquil, affluent residential area, offering easy access to Winter Park's city centre and Orlando's city centre, as well as being a short distance from Baldwin Lake and Rollins College.
This one-bedroom, one-bathroom flat accommodates two guests, featuring a newly refurbished kitchen with a fridge and microwave, air conditioning, free Wi-Fi, and a dedicated parking space, with long-term stays available for extended visits.

This charming house is located just a short distance from Winter Park's bustling centre, within a 4-kilometre radius of the downtown area, Park Avenue and the Saturday Farmers Market. It has consistently received excellent ratings from previous guests, scoring highly for location, cleanliness, and overall user experience.
The property offers two bedrooms and two bathrooms, accommodating up to five guests comfortably. It is fully equipped with modern amenities such as a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a garden, and parking.

This College Park flat is ideally located near the intersection of College Park and Ivanhoe Village, offering easy access to major hospitals such as AdventHealth and Orlando Regional Medical Center, and within a short drive of attractions including Universal Orlando Resort.
The two-bedroom, one-bathroom apartment sleeps two guests, is fully furnished and includes air conditioning, internet access, and a starter pack for short or long-term stays.

This Downtown Orlando flat offers a central location, within 8-24 kilometres of the Amway Center, Lake Eola, International Drive, and the Orlando Convention Center, with Walt Disney World Resort and Universal Orlando Resort also within a reasonable driving distance.
The self-catering apartment sleeps three, features a queen-size bed, 65” smart TV, fully equipped kitchen, washer/dryer, free parking, and access to a swimming pool, fitness centre, and garden.

This Winter Park holiday home is conveniently located less than 1.6km from the Albin Polasek Museum and Sculpture Gardens and Rollins College, and within 3.2km of the Morse Museum of American Art and Casa Feliz Historic Home Museum, offering easy access to Winter Park Station within a 20-minute walk.
The self-catering property features one bedroom, one bathroom, sleeping up to two guests, and includes free Wi-Fi, a TV, and parking; nearby attractions include the Albin Polasek Museum and Sculpture Gardens.

This Orlando duplex, ideally located minutes (approximately 5km) from AdventHealth and Orlando Health hospitals, offers easy access to central Orlando attractions.
The one-bedroom, one-bathroom apartment sleeps three, features a fully equipped kitchen, smart TV, Alexa, in-unit laundry, a private garden, and two off-street parking spaces.

This Orlando apartment, near Baldwin Park, offers easy access to Baldwin Park Lake and the Cady Way Trail, a short walk from various amenities.
The two-bedroom, one-bathroom dwelling sleeps three guests, boasting a full kitchen, private patio with sunset views, and access to shared laundry facilities and two additional guesthouses in the backyard.

This single-storey house is situated in East Orlando, just 12 minutes from the University of Central Florida and 40 minutes from Orlando International Airport. It has received excellent user, location, and cleanliness ratings.
The property spans 149 square metres and comfortably accommodates up to 8 guests in its four bedrooms and two bathrooms. Amenities include a private pool, a dock, a fully equipped kitchen, a garden, and high-speed internet.

This Orlando apartment, near Baldwin Park Lake, is conveniently located approximately 11 kilometres from Downtown Orlando and within 19 kilometres of attractions such as Church Street Station and the Holy Land Experience.
This spacious 131 square metre dwelling boasts one bedroom, three bathrooms, and comfortably sleeps eleven guests, offering free private parking, a fully equipped kitchen, laundry facilities, a garden, and free Wi-Fi.

This apartment is located in Winter Park, a charming neighbourhood just 2 kilometres from Park Avenue and its diverse dining scene, and 40 kilometres from Orlando International Airport. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment can comfortably accommodate up to four guests and features a spacious and open layout. Guests can enjoy a peaceful outdoor patio, a well-equipped kitchen, air conditioning, a garden, a fitness centre, and parking.

This completely renovated guesthouse is located in the quiet Eola Heights Historic District, just under a kilometer from Lake Eola and a short walk from the Orange County Courthouse and the Central Business District. The apartment has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travelers.
The apartment has one bedroom with a queen-sized bed and a pull-out sofa, comfortably accommodating up to four guests. The apartment comes equipped with a full kitchen, two flat-screen TVs, cable, Wi-Fi, a washer and dryer, and air conditioning.

This 19 square metre studio apartment in Orlando's Fairview Shores district is situated near a lake, offering proximity to Florida Mall and Universal Studios, located 22 kilometres away.
The accommodation features air-conditioned living space for two guests, with a refrigerator, microwave, private bathroom, and access to an outdoor swimming pool and free on-site parking, with motor boating and swimming available nearby.