Vacation rentals in Winter Park, FL

About: This unique tiny house is located in Orlando's Lakefront district, a peaceful neighborhood with easy access to the city center and major tourist attractions like Walt Disney World and Universal Orlando Resort. It has received excellent location ratings from previous guests.

The house features a cozy and comfortable interior design, with air conditioning, a flat-screen TV, and a kitchen equipped with a fridge, microwave oven, and dishwasher. Outside, guests can enjoy a private picnic area, sun terrace, and garden, as well as on-site water sports facilities.

About: This house is located in Old Winter Park, within walking distance of East End Market, shops, restaurants, and entertainment options, and close to Baldwin Park Lake and Blue Jacket Park.

It's got an excellent user rating.

It's a 4-bedroom, 2-bathroom house with a floor area of 2200 square feet and a guest capacity of 10.

It has a fully updated kitchen, comfortable beds and linens, an open floor plan and spacious dining area, a private pool and BBQ area, air conditioning, a swimming pool, a garden, parking, and it's pet-friendly.

About: This beautiful house is located in Maitland, within a 9-minute walk from Maitland Station and 3 miles from Lake Lily Park, Altamonte Mall, and Winter Park Village. It has received excellent user ratings.

The house has a floor area of 2800 square feet and can accommodate up to 8 guests. It has 5 bedrooms, 4 bathrooms, a fully equipped kitchen, a private pool, a fireplace, air conditioning, a garden, and parking.

About: This 3-bedroom, 2-bathroom house is located in Altamonte Springs, near Altamonte Mall, Cranes Roost Park, and Sanlando Park. It has an excellent user and location rating.

The 1650 square feet house features a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a spa, and parking. It also has a riverfront location, a fenced private yard, a fireplace, and free Wi-Fi. Housekeeping is available on request.

About: This apartment is located in a quiet residential neighborhood in Altamonte Springs, near Crane's Roost Park, offering a peaceful ambiance and proximity to local attractions. It has received excellent ratings for its location, cleanliness, and user experience.

With four bedrooms, three bathrooms, and a guest capacity of eight, this apartment provides ample space and comfort for families or groups. It features a fully equipped kitchen with modern appliances, air conditioning, and a private screened-in pool, perfect for relaxation and entertainment. The apartment also offers access to a garden and parking, ensuring convenience and privacy for guests.

About: This house is located in College Park, a charming district in Fairview Shores, near Dubsdread Golf Course, Lee Road Shopping Center, and AdventHealth Orlando. It has excellent user, location, and cleanliness ratings.

The house has 3 bedrooms, 2 bathrooms, and a floor area of 1190 square feet. It can accommodate up to 8 guests.

It features a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a spa, and parking. It also has a private water park and a spa tub for relaxation and entertainment.

About: Located in Azalea Park, this accommodation is 15 minutes from the airport and downtown Orlando, and 30 minutes from Disney and Universal. It has excellent user, location, and cleanliness ratings.

With a floor area of 2000 square feet, this accommodation has 4 bedrooms and 2 bathrooms.

This accommodation is unique because it has a private lot with 6 parking spaces, a pet-friendly large yard, a 7ft deep pool with a child safety fence, a spacious and beautifully decorated interior, 50" smart TVs in the living room and master bedroom, a desk and workstation, a fully equipped kitchen, and a separate entrance from the mother-in-law suite.

About: This centrally located vacation home in Casselberry is near Winter Park Village, Lil 500 Go-Karts, and Red Bug Lake Park. It is rated excellent by previous guests.

With 1600 square feet of floor area, it can accommodate up to 8 guests with its 3 bedrooms and 2 bathrooms.

This accommodation has a fenced private yard, a fully equipped kitchen, free WiFi, and a smoke-free environment. It also has outdoor amenities such as a water park and barbecue grills.

About: This 2-bedroom, 2-bathroom apartment is located in Ventura Country Club, 6 miles from Orlando airport and within 20-30 minutes of Disney World, Sea World, Universal Studios, and Cape Canaveral. It has an excellent user rating.

The 850-square-foot apartment can accommodate up to 6 guests and features a fully equipped kitchen, three flat-screen TVs, bunk beds with double, twin, and trundle options, a private screened patio, linens, pillows, beach towels, high-speed internet, free long-distance calls, a washer and dryer, air conditioning, a swimming pool, a Jacuzzi, a terrace/balcony, a garden, and parking.

About: This luxurious 4-bedroom, 4-bathroom house is located in the heart of Winter Park, just steps away from Full Sail University, Albin Polasek Museum, Kraft Azalea Gardens, and Winter Park Village. It has received excellent user ratings.

The house has a floor area of 3000 square feet and can accommodate up to 8 guests. It features a private pool, a fireplace, a fully equipped kitchen, air conditioning, a terrace, a garden, and parking. Guests can also enjoy free WiFi and housekeeping services.

About: This accommodation is located in Azalea Park, near major attractions. It is surrounded by lush greenery and offers a peaceful ambiance.

The accommodation has received excellent ratings for its location, cleanliness, and user experience. It has 3 bedrooms, 2 bathrooms, and can accommodate up to 6 guests.

It features a private backyard with a pool and kiddie pool, a game room with a bar, and a fully equipped kitchen for family gatherings. The spacious and comfortable interior provides a relaxing space for guests. The accommodation is conveniently located near attractions and offers easy access to the city center.

About: Located in the peaceful Dixie Belle neighborhood, this apartment offers a tranquil escape just 10 minutes from downtown Orlando and Orlando International Airport. With excellent user ratings, it guarantees a comfortable and memorable stay.

This spacious split-floor plan apartment accommodates up to 6 guests in 3 bedrooms and 2 bathrooms. Its unique features include a private outdoor pool, a custom-designed interior with luxurious finishes, and smart TVs in all rooms.

About: This lakefront house is located in Orlando, near Camping World Stadium (1.3 miles) and Amway Center (2.3 miles). It has excellent user and location ratings, and very good cleanliness ratings.

The house has 5 bedrooms, 4 bathrooms, and a fully equipped kitchen. It also has a private pool, hot tub, and boating access on the lake.

Wellness facilities include a sauna and hot tub. The spacious outdoor terrace has lake views.

About: In Altamonte Springs, near Altamonte Mall, Sanlando Park, and Cranes Roost Park, The Chloe By Evrh welcomes you in a family-friendly atmosphere. Rated excellent by its guests, this resort offers a waterfront location with a private pool and fenced yard.

The resort features 3 bedrooms and 2 bathrooms, upscale amenities such as a fireplace and a gourmet kitchen, free WiFi, and gas grills. It is also conveniently located near various attractions, including RDV Sportsplex.

About: The Olivia by Evrh is a resort located in the heart of Altamonte Springs, near RDV Sportsplex, Altamonte Mall, and Cranes Roost Park. It is a family-friendly resort with a very good user rating.

The resort has 3 bedrooms, 2 bathrooms, a private pool and fireplace, a fully equipped kitchen, free WiFi and TV, and a garden. It is also pet-friendly and has parking.

The Olivia by Evrh is a great place to stay for travelers visiting Altamonte Springs. It is close to major tourist attractions, has a variety of amenities, and is family-friendly.

About: This private 4-bedroom, 2-bathroom house is located in Casselberry, near Lake Casselberry and Casselberry Golf Club. It has received excellent ratings for its location, cleanliness, and user experience.

The house features a gourmet kitchen with gas stove, granite countertops, and top-of-the-line appliances, a master suite with Jacuzzi and walk-in shower, TVs with streaming services (Netflix, HBO Max, ESPN+, Disney+) and home cinema, a large backyard with private landscaping and lighting, and a guest house. It is pet-free and has parking.

About: This house is in the heart of Orlando, near Lake Eola, Kia Center, and Camping World Stadium. It's close to many shops, restaurants, and attractions.

The house has a very good rating from guests.

It has 2 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. The floor area is 1400 square feet.

The house has a private pool, a patio, free WiFi, a kitchen with a refrigerator and oven, a water park and spa tub on-site, barbecue grills, and a garden.

About: This apartment is in Thornton Park Historic District, 5 blocks from Lake Eola and its attractions. It has an excellent user, location and cleanliness rating.

The apartment has 2 bedrooms, 2 bathrooms and a guest capacity of 6.

It has a fully equipped kitchen, air conditioning, internet, a swimming pool, a garden, and parking. It also has a heated salt pool, Jacuzzi, and gazebo. It is close to major attractions like Lake Eola, Disney World, and Universal Orlando.

About: Located in the heart of Fern Park, this house is within easy reach of Winter Park Village and Lil 500 Go-Karts. It is rated excellent by users.

The house has a spacious 3-bedroom layout with a floor area of 2200 square feet and can accommodate up to 8 guests.

This accommodation is unique because it offers a private pool, spa tub, fireplace, private garden, free WiFi, sofa bed, and is close to major tourist attractions.

About: This spacious 3-bedroom home is located in the charming city of Casselberry, just 3 miles from the renowned Altamonte Mall. The home enjoys an excellent location rating and user reviews, with guests praising its cleanliness and amenities.

The home comfortably accommodates up to 7 guests and features a fully equipped kitchen, free WiFi, air conditioning, and a private swimming pool for relaxation and enjoyment. Guests can also enjoy outdoor cooking and entertainment on the barbecue grills, or relax in the serene garden area. The home is also conveniently located near Cranes Roost Park and Red Bug Lake Park, offering ample opportunities for outdoor recreation and nature appreciation.

About: Centrally located in a safe and quiet neighborhood in Downtown Orlando, within walking distance of Lake Eola and Thornton Park, this 1750 square feet apartment with 3 bedrooms and a capacity for 8 people has received excellent reviews for its location, cleanliness, and facilities.

It features a unique mid-century design with a Zen garden and fountains, three bedrooms with king-size beds and two bathrooms, a fully equipped kitchen with a Keurig coffee maker and appliances, a foosball table, and an Xbox One. The landscaped front and back yards with a pergola and a grill are perfect for relaxing or entertaining guests.

About: This apartment is located in Colonialtown North, near Downtown Orlando and Winter Park. The street is quiet, with restaurants and shopping nearby. It has excellent user, location and cleanliness ratings.

This 3-bedroom, 2-bathroom apartment can accommodate up to 6 guests.

It has a kitchen with a fridge, freezer, microwave oven and dishwasher, as well as air conditioning, a garden, and parking. It also has access to all amenities on the property.

About: This house is located in Winter Park, Florida, near Full Sail University, Kraft Azalea Gardens, University of Central Florida, Winter Park Village, and East Orlando Shopping Center. It is a family-friendly destination with excellent user, location, and cleanliness ratings.

The house has a floor area of 1400 square feet, 3 bedrooms, and 2 bathrooms. It features a private fenced yard, a fireplace, a kitchen with a refrigerator and oven, free WiFi, water park access, barbecue grills, and a garden.

About: This 3-bedroom house is located in the heart of Altamonte Springs, a charming city with a vibrant atmosphere. It is situated near the Altamonte Mall and Cranes Roost Park, making it an ideal base for exploring the area's attractions.

The house has received excellent ratings for its location, cleanliness, and user experience. It offers a spacious floor area of 2200 square feet and can accommodate up to 8 guests.

The house boasts a fully equipped kitchen, free WiFi, air conditioning, a private fenced yard, and parking. It also features a unique interior design with comfortable furnishings, creating a warm and welcoming ambiance for guests.

About: This accommodation is located in Winter Park, away from tourist areas, near Winter Park downtown and major airports (MCO, SFB). It's centrally located between theme parks and Winter Park downtown.

It has excellent user, location and cleanliness ratings. It can host up to 7 guests in 4 bedrooms and 2 bathrooms.

It features a private backyard with mature landscaping, a screened porch with BBQ, memory foam mattresses and adjustable bed base, a 65" TV with Roku, a kitchen with fridge, microwave oven and dishwasher and air conditioning.

About: This waterfront home is located in the exclusive Dubsdread Golf Course area, near Orlando Science Center and Advent Health. It has excellent user, location, and cleanliness ratings.

The house has 3 bedrooms, 2 bathrooms, and a floor area of 2500 square feet. It can accommodate up to 7 guests.

The house features a fully equipped kitchen, free WiFi, a spacious living area, a private backyard with a patio and barbecue grill, a swimming pool, a terrace/balcony, a garden, a fitness center, and a tennis court. It also has access to a water park and an arcade.

About: This house is in Orlando's College Park district, near Lake Ivanhoe and Orlando Science Center. It's also just 2.9 mi from Kia Center.

It has excellent user, location, and cleanliness ratings.

The house has 3 bedrooms, 1780 square feet of floor area, and can accommodate up to 8 guests.

It has a fully equipped kitchen, a private balcony with outdoor seating, a garden, a tennis court, parking, and complimentary Wi-Fi.

About: This apartment is located in the Ventura district, near Ventura Country Club, within 10km of Lake Conway and Rio Pinar Country Club. It is conveniently located to major tourist attractions and landmarks.

The apartment is rated very good by users and has a very good location rating.

The apartment has 2 bedrooms and a fully equipped kitchen.

This apartment has a swimming pool, a Jacuzzi, a fitness center, a tennis court, a spa, a restaurant, a bar, a garden, a terrace/balcony and a parking. It also has access to a water park and on-site barbecue grills.