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

Luxury Ranch is a farm stay located in College Park, Orlando, just 20 minutes from Walt Disney World and 17 minutes from Universal Orlando Resort, making it a great base for exploring the area's attractions. This property has received excellent reviews from previous guests.
The farm has four bedrooms and four bathrooms, comfortably accommodating up to 13 guests. Guests can enjoy a range of amenities, including a heated pool, a garden, a BBQ grill, and board games.

This lakefront B&B offers private guest quarters in downtown Orlando, providing panoramic skyline views and direct lake access within 1 kilometre of the city's core attractions.
This accommodation sleeps up to six guests across one bedroom and a living area with two sofa beds, featuring a kitchenette with a fridge, freezer, and microwave, air conditioning, a swimming pool, garden, parking, and a basketball hoop.

This fully furnished two-bedroom house is situated near Baldwin Park, a short drive (minutes) from Downtown Orlando, Orlando International Airport (MCO), and several theme parks.
The 2-bathroom property, sleeping up to 5 guests, boasts a private backyard with a fire pit, high-speed internet, a fully equipped kitchen including a dishwasher, and keyless entry; peaceful walking trails are also nearby, with Downtown Disney easily accessible.

This Casselberry house, near major highways and a short drive (approximately 32km) from Walt Disney World and Universal Studios, offers easy access to Orlando International Airport.
Sleeping up to 10 guests in three bedrooms and two bathrooms, this fully remodelled property features a fully equipped kitchen, private fenced backyard with fire pit and patio, yard games (cornhole and axe throwing), an outdoor grill, and smart TVs.

This ground-floor Winter Park apartment, situated in Baldwin Park, is a short walk from both Baldwin Park's town centre and Park Avenue, and less than 0.16 km from a playground and a large dog park.
The two-bedroom, one-bathroom flat sleeps four, features a private patio with a barbecue, two bikes for guest use, and includes starter supplies; handicap accessibility is provided by 36" doors and a bath grab bar.

This two-bedroom, two-bathroom apartment is situated in Orlando's Lake Lawsona Historic District of Thornton Park, within walking distance of Lake Eola Park and a short drive (approx. 24km) from Orlando International Airport (MCO).
The 130 square metre property offers a modern interior with two queen-sized beds, a 75-inch smart TV, full kitchen, in-unit laundry, and free private parking; accommodating up to five guests and close to the Dr Phillips Center for the Performing Arts.

This Winter Park guesthouse is conveniently located near Full Sail University, within a 1.6km radius of Baldwin Park and a 8km drive from the University of Central Florida.
Offering a private downstairs bedroom and bathroom, this modern condo sleeps four guests and boasts a full kitchen, swimming pool access, and on-site massage and dance lessons (fees apply).

This three-bedroom apartment is located in Altamonte Springs, just a short drive from the Altamonte Springs Hospital and within easy reach of major attractions like Disney World, Universal Studios, and Downtown Orlando. It has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment offers ample space for up to six guests, with a fully equipped kitchen, a laundry room, and parking. Guests can enjoy a peaceful and quiet stay with modern amenities such as air conditioning, comfortable beds, and flat-screen TVs in every room.

This Thornton Park flat is less than 1.6km from Lake Eola and the Dr. Phillips Center for the Performing Arts, and within 4.8km of Camping World Stadium.
This two-bedroom, one-bathroom apartment sleeps four, includes in-unit laundry, and offers excellent access to Thornton Park's restaurants and shops.

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 five-bedroom flat in Winter Park, 1.7 kilometres from the Central Florida Fairgrounds and 2.2 kilometres from Kraft Azalea Gardens, offers convenient access to the Mall at Millenia and Winter Park Village, as well as venues such as the Kia Centre and Camping World Stadium.
This accommodation sleeps up to eleven guests and features two bathrooms, air conditioning, and Wi-Fi, making it a suitable base for exploring the area.

This Orlando apartment, situated in the Lawsona-Fern Creek neighbourhood, is a 13-minute walk (approximately 1km) from Lake Eola Park and offers easy access to attractions such as the Florida Mall and Universal Orlando Resort.
The two-bedroom, one-bathroom property sleeps six guests and features a fully equipped kitchen with dishwasher, a terrace, air conditioning, Wi-Fi, and a workspace, perfect for families or groups visiting the city.

This one-bedroom cottage is located in a residential area of Orlando, within walking distance of the city centre and a short drive (around 10 km) from Universal Studios.
The self-contained property offers a private entrance and bathroom, a small kitchen with a fridge, microwave and coffee maker, and a porch for relaxing.

This downtown Orlando guest house is situated just over 1.6 kilometres from Church Street Station and Camping World Stadium, and a 17-minute walk from the Kia Centre.
The B&B offers one bedroom, one bathroom, and accommodation for two guests, with free Wi-Fi, air conditioning, and on-site parking provided by a private host.

This charming bed and breakfast is located in Audubon Park, just a short drive from downtown Orlando and its famous theme parks. The neighbourhood is a peaceful residential area, offering a welcome respite from the hustle and bustle of the city. The B&B enjoys excellent ratings for location, cleanliness, and overall guest experience.
The guest room features a private entrance and parking space, ensuring privacy and convenience. Guests can enjoy a comfortable stay with amenities such as a patio, a retractable awning, a space heater, and a window AC unit. Complimentary beverages, Wi-Fi access, and a lockbox with a key fob are also provided.

This Winter Park cottage boasts a unique split-building design, situated in a quiet Orlando neighbourhood approximately 16-24 km from Universal Studios and 32-35 km from Orlando International Airport.
The self-contained unit sleeps three, featuring a queen bed, full kitchen with dishwasher, private patio and deck, a full-size washer/dryer, and dedicated parking for two cars, plus access to a communal BBQ area.