Find short term rentals in Winter Park, FL at the best prices

This Ventura apartment in Orlando is conveniently located near major theme parks, approximately 13km from Downtown Orlando and 43km from Walt Disney World Resort.
This two-bedroom, two-bathroom property sleeps four (with a fifth guest possible for an extra fee), offering a fully equipped kitchen, free Wi-Fi, in-unit laundry, a balcony, and access to a community pool, hot tub, tennis court, and golf course; free parking is available within the gated community.

This recently renovated Winter Park duplex, located minutes from Rollins College and Park Avenue, offers convenient access to downtown Winter Park (a short drive) and theme parks (approximately 48 kilometres away).
The two-bedroom, two-bathroom property sleeps four guests and features two smart TVs with Fire Sticks offering access to over 12,000 streaming channels, private garage access, and is pet-friendly (pet fee applies).

This Fairview Shores flat is located approximately 9 kilometres from the Kia Centre and Church Street Station, offering convenient access to downtown attractions.
This ground-floor studio apartment, measuring 19 square metres, accommodates up to four guests and features air conditioning, a private bathroom, a refrigerator, microwave, free WiFi, and access to an outdoor swimming pool, with pet-friendly policies and free on-site parking available.

This two-bedroom apartment is located in Winter Park, within a 15-minute walk of the Morse Museum of American Art and Casa Feliz Historic Home Museum, and within 2 kilometres of Rollins College and the Albin Polasek Museum and Sculpture Gardens. The apartment is situated in a quiet and convenient location, perfect for exploring the city's attractions.
The self-catering apartment can accommodate up to 4 guests and has a fully equipped kitchen, a comfortable living area, a private balcony, and a shared outdoor pool. Guests can enjoy free Wi-Fi, air conditioning, and a smoke-free environment.

This three-bedroom house is situated in a well-established Winter Park neighbourhood, within a short walking distance of Park Avenue's shops and restaurants, Rollins College, and Lake Virginia.
This family-friendly property offers three bedrooms, two and a half bathrooms, a fully equipped kitchen including a dishwasher, a swimming pool, and a garden, sleeping up to six guests and is close to local amenities.

This Winter Park bungalow, ideally situated near Orlando, offers easy access to numerous attractions and is within convenient driving distance of major theme parks.
Sleeping up to eight guests, this two-bedroom, two-bathroom property boasts a well-equipped kitchen, multiple 55" Roku TVs, a dedicated workstation, and outdoor gazebo access.

This charming cottage is situated just a short distance from Altamonte Springs' downtown area, offering a peaceful retreat close to shops, restaurants and the Altamonte Springs Arts & Recreation Centre. The property has received excellent ratings for its location, cleanliness and overall experience.
The cottage, which can accommodate up to four guests, is fully equipped with a modern kitchen and a luxurious bathroom. Guests can enjoy the serene setting by the lake, with access to a paddle boat and a hammock, or relax in the private garden.

This Lake Eola Heights apartment is situated less than 1.6km from Lake Eola Park and within a 4.8km radius of the Kia Centre and Camping World Stadium in Orlando, Florida.
The one-bedroom, one-bathroom flat sleeps three guests and features a fully equipped kitchen, washing machine, balcony, and access to an on-site garden and barbecue grills; enjoy nearby scenic walks and recreational activities at Lake Eola Park.

This two-bedroom apartment is located just 0.5 kilometres from Park Avenue and 0.3 kilometres from Winter Park Village, two lively areas with many restaurants, shops, and entertainment options. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The spacious flat can comfortably accommodate up to six guests. Amenities include a swimming pool, hot tub, a fully equipped kitchen, high-speed internet, and complimentary bikes for exploring the area.

This charming one-bedroom house is situated in Altamonte Springs, just 18 kilometres from downtown Orlando and Church Street Station, offering a peaceful escape from the city's hustle and bustle. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
The 42 square metre house comfortably accommodates two guests and features a separate bedroom and living area. Guests can enjoy a fully equipped kitchen, a private garden, a spa, free Wi-Fi, air conditioning, and direct access to Lake Marion, complete with a canoe for exploring the tranquil waters.

This Winter Park apartment is situated just 0.5 km from Park Avenue and 0.3 km from Winter Park Village, offering easy access to Winter Park's key attractions.
The 116-square-metre property boasts two bedrooms, two bathrooms, sleeps five guests, and includes a swimming pool, spa, and on-site parking, plus high-speed internet access.