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

This one-bedroom flat is situated in Winter Springs, a tranquil community located northeast of Orlando, providing straightforward access to shopping, dining, parks, and major roads, with Lake Jesup and Trotwood Park in close proximity.
This 764 square meter apartment, ideal for two guests, features a fully equipped kitchen, open-plan living and dining areas, and access to community amenities including a swimming pool, fitness centre, and tennis court, with nearby outdoor recreation at Lake Jesup and Trotwood Park.

This renovated Casita, located in downtown Orlando near Lake Eola and Delaney Park, is a 12-minute walk from Church Street Station and within 1.3 km of the Amway Center and 4 km of Camping World Stadium.
This 2-bedroom, 1-bathroom apartment offers 300 square metres of space, sleeps up to 7 guests, and includes free Wi-Fi, private parking, a fully equipped kitchen, and air conditioning.

This Baldwin Park holiday home is situated within 5km of Orlando Fashion Square, East Orlando Shopping Centre, The Plaza Theatre, Harry P. Leu Gardens, and Lake Virginia.
This 102-square-metre property boasts two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, private fenced yard with patio and barbecue, plus free Wi-Fi.

This Altamonte Springs holiday home is conveniently located less than 1.6km from Cranes Roost Park and Uptown Altamonte, offering easy access to shops and restaurants, and within 56km of Orlando International Airport (MCO) and Sanford Airport (SFB).
Sleeping six, this two-bedroom, one-bathroom property boasts a king and two queen beds, a fully equipped kitchen with island seating, a private garden, swimming pool, jacuzzi, and parking; an additional one-bedroom apartment is available upon request.

This two-bedroom, one-bathroom Orlando duplex is situated in the Mills 50 district, within walking distance of AdventHealth Orlando, the Ronald McDonald House, and the SunRail station.
This fully furnished apartment, sleeping four, boasts a kitchen with dishwasher and microwave, in-unit laundry, high-speed Wi-Fi, and is conveniently located near Mead Gardens and Harry P. Leu Gardens, offering easy access to theme parks and beaches.

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 one-bedroom Orlando condo enjoys a central downtown location, within a 5-15 minute drive of the Amway Center, Lake Eola Park, International Drive, and the Orange County Convention Center.
The self-catering apartment sleeps three, features a fully equipped kitchen, two smart TVs, in-unit laundry, a dedicated workspace, and free private parking, plus access to a swimming pool, garden, and fitness centre.

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 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 Winter Park house, ideally located in a prime foodie area, offers easy access to Downtown Orlando, Winter Park and College Park (8-11 km), Universal Studios (24-32 km), Disney World (48-56 km), and Wekiwa Springs State Park (24-32 km).
The two-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen with dishwasher and washer/dryer, a private fenced backyard with gazebo, multiple large-screen TVs, and parking for two vehicles.

This Orlando apartment, situated in the Colonialtown North district, is less than 1.1 kilometres from Harry P. Leu Gardens and within 3.2 kilometres of the Plaza Theatre.
The one-bedroom flat sleeps two guests and includes a kitchen with fridge and microwave, a washing machine, a garden, parking, and internet access; nearby attractions include the Orlando Museum of Art.

This charming bed and breakfast is located in Goldenrod, just 18 kilometres from downtown Orlando, 25 kilometres from Universal Studios and International Drive, and 35 kilometres from Magic Kingdom and SeaWorld. It's situated in a quiet, residential area, perfect for families seeking a relaxing getaway.
The accommodation is a spacious 3-bedroom condo, comfortably sleeping two guests, and is shared with a couple, their 7-year-old child, and a friendly golden doodle. Guests have access to all areas of the condo except the host's bedroom and the child's bedroom, ensuring privacy. The B&B features a fully equipped kitchen, air conditioning, a swimming pool, a garden, a fitness center, and free parking.

This two-bedroom apartment is situated in the peaceful Winter Park neighbourhood, just a short distance from major theme parks, downtown Orlando, and the Avenue, making it an ideal base for exploring the city. The property has received excellent ratings for its cleanliness, location, and overall guest experience.
The apartment is spacious and comfortably sleeps up to eight guests, with three queen beds and a pull-out sofa. Guests can enjoy modern amenities, including high-speed Wi-Fi, a smart TV with streaming services, a washer/dryer, and free designated parking.

This Winter Park duplex is situated in the downtown area, less than 0.32 kilometres from Park Avenue and within walking distance of Central Park, the Morse Museum of American Art, and Rollins College.
The two-bedroom, one-bathroom flat sleeps four guests and offers amenities including a shared heated pool, hot tub, and barbecue area, plus bikes for exploring the local area.

This Orlando cottage, situated in Colonialtown North, is less than 1.6km from the Orlando Museum of Art and AdventHealth Orlando, and approximately 4.3km from the Kia Center.
The self-catering property sleeps two guests in one bedroom and one bathroom, and includes in-unit laundry facilities, a hairdryer, and air conditioning.

This mid-century house is located in Goldenrod, a 15-minute drive from downtown Orlando, a 10-minute drive from Park Ave, and a 10-minute drive from UCF. The property has received excellent ratings for its cleanliness, location, and overall experience.
The house has three bedrooms and two bathrooms, comfortably accommodating up to 16 guests. The home offers a range of amenities, including a fully equipped kitchen, a spacious garden, air conditioning, and ample parking.