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

This house is located in Altamonte Springs, just 5 kilometres from Altamonte Mall, Maitland Art Center, and Cranes Roost Park, making it easy to explore the area. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The property is a 3-bedroom, 2-bathroom house with a floor area of 153 square metres, comfortably accommodating up to 6 guests. This family-friendly home offers a range of amenities including a swimming pool, terrace, garden, and parking, as well as a fully equipped kitchen and air conditioning for a comfortable stay.

This 3-bedroom, 3-bathroom townhome is centrally located in Orlando's College Park district, a 5-minute walk from the Great Southern Box Company Food Hall & Bar, and within 20 kilometres of Walt Disney World, Universal Studios, and the Mall at Millenia.
This family-friendly property, which accommodates up to six guests, features air conditioning, Wi-Fi, a fully equipped kitchen, a garden, a sauna, and a detached 2-car garage, with Orlando Health and downtown Orlando attractions a mere 10-minute drive away.

This centrally located flat in Orlando provides unparalleled convenience, situated a short 6-kilometre drive from Walt Disney World Resort and Universal Orlando Resort, with easy access to the I-4 for onward travel and a mere 20-kilometre journey to Orlando International Airport (MCO).
This family-friendly apartment accommodates up to 8 guests, offering 2 bathrooms, air conditioning, and a kitchen equipped with a fridge, microwave oven, and dishwasher, alongside the convenience of included internet and pet-friendly policies, all within a walkable distance to local shops and restaurants.

This modern two-bedroom flat is situated in the Goldenrod district of Winter Park, offering proximity to Park Avenue and Rollins College, and is a short drive from Orlando's theme parks.
This family-friendly apartment provides a fully equipped kitchen, air conditioning, a private patio, and parking, with guest capacity for five and a user rating of excellent.

This self-catering apartment in Orlando's Rio Pinar neighbourhood is conveniently located approximately 15-21 kilometres from attractions such as Church Street Station, the Kia Center, Camping World Stadium, and the Holy Land Experience.
The one-bedroom, one-bathroom flat sleeps three guests and features a private terrace with garden views, free Wi-Fi, private parking, air conditioning, and a fully equipped kitchen.

This luxury two-bedroom condo is situated in Downtown Orlando, within a 8-24km radius of attractions such as the Amway Center, Lake Eola, and International Drive.
The 2-bathroom apartment sleeps six guests and boasts a fully equipped kitchen, in-unit laundry, free private parking, and two king-size beds, plus Smart TVs; nearby activities include exploring Lake Eola Park or visiting the Orlando Convention Center.

This two-bedroom apartment is situated in the centre of Winter Park, just 0.4 kilometres from Park Avenue and 0.3 kilometres from Winter Park Village, offering easy access to shops, restaurants and entertainment. The apartment has excellent user, location and cleanliness ratings.
The apartment is 110 square metres in size and comfortably sleeps four guests. It features a modern design, a fully-equipped kitchen, a balcony, a swimming pool, a jacuzzi, a spa and a garden.

This two-bedroom apartment is conveniently located in Ventura, Orlando, just six miles from Orlando International Airport and 20-30 minutes from Disney World, Sea World, and Universal Studios. It has received excellent user ratings, making it a popular choice for travellers. This 79 square metre apartment comfortably sleeps six guests. The apartment features a fully equipped kitchen, a private patio, a swimming pool, a Jacuzzi, and a garden, offering a relaxing and enjoyable stay.

This flat is situated in central Orlando, 720 metres from Pirate's Dinner Adventure and 1.04 kilometres from Titanic the Experience.
This 36 square metre flat accommodates up to four guests and features a kitchen with a fridge, microwave oven and dishwasher, air conditioning, a swimming pool, a balcony, and on-site parking.

This Fairview Shores holiday home is located within 3km of Lee Road Shopping Centre, The Centre of Winter Park Shopping Centre, and Mead Garden, offering easy access to shopping and green spaces. The property has received excellent ratings for location, cleanliness, and overall experience.
This three-bedroom property provides 141 square metres of space for up to six guests. The home has a fully equipped kitchen, a private garden, free Wi-Fi, air conditioning, and parking.

This charming cabin is located in Azalea Park, just 15 kilometres from Orlando International Airport and downtown Orlando, and within 45 kilometres of major theme parks like Disney, Universal, and Sea World. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The cosy cottage has one bathroom and can accommodate two guests. It includes a fully equipped kitchenette, a comfortable queen bed, fresh linens, towels, and complimentary coffee, along with a private entrance, a secluded backyard, and free parking.

This Winter Park holiday home is situated a 15-minute walk from the Casa Feliz Historic Home Museum and Morse Museum of American Art, and within 3.2km of Rollins College and Kraft Azalea Gardens.
This 83 square metre property offers three bedrooms, one bathroom, sleeping up to four guests, and features a fully equipped kitchen, in-house laundry, a patio, and garden; it's also smoke-free, ideal for allergy sufferers.

This Orlando apartment is centrally located in downtown Orlando, within walking distance of Lake Eola Park, the Amway Center, and the Dr. Philips Center for the Performing Arts.
The 70 square metre (753 square feet) self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes amenities such as Wi-Fi, air conditioning, a garden, and parking; nearby attractions include the Florida Mall and Orlando International Premium Outlets.

This Sky Lake flat is located approximately 3 kilometres from Florida Mall and 7 kilometres from Holy Land Experience, offering easy access to Universal Studios Orlando and SeaWorld Orlando, with Orlando International Airport just 9 kilometres away.
This 14 square metre studio apartment accommodates up to four guests and features air conditioning, a kitchenette with a refrigerator and microwave, complimentary WiFi, and on-site private parking, with a refundable cash damage deposit of US$50 required upon arrival.

This two-bedroom apartment in Winter Park is conveniently located just a short walk from Park Avenue and Winter Park Village, offering easy access to a range of shops, restaurants, and bars. The apartment has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travellers seeking a comfortable and well-maintained stay.
The apartment is modern and stylish, with a newly renovated kitchen and a tranquil sunroom, comfortably accommodating up to three guests. Enjoy access to a swimming pool overlooking the lake, paddleboards, shuffleboard courts, picnic tables, and regular housekeeping, ensuring a relaxing and enjoyable stay.

This Sky Lake flat offers easy access to Orlando International Airport (9 km) and Florida Mall (3 km), placing guests within reach of Universal Studios Orlando, SeaWorld Orlando, and The Wizarding World of Harry Potter.
This 14 square metre studio apartment accommodates two guests with air conditioning, a kitchenette featuring a refrigerator and microwave, and complimentary WiFi, with free on-site private parking also provided.