Vacation rentals in Winter Park, FL

About: This private studio in Orlando's College Park neighborhood is surrounded by small-town charm yet conveniently located just 10 minutes from Winter Park and Downtown Orlando. With excellent user, location, and cleanliness ratings, this studio is a top choice for travelers seeking a comfortable and convenient stay.

The studio features a modern layout with a fully equipped kitchen, a spacious work area, and a private backyard for relaxation. It accommodates up to 2 guests and includes amenities such as a Smart TV, fast WiFi, a clothes washer and dryer, and free street parking.

About: This cozy cottage is conveniently located within minutes of Winter Park, College Park, Disney, and Universal in the heart of Orlando. It has excellent user, location, and cleanliness ratings.

The cottage has 1 bedroom and 1 bathroom and can accommodate up to 5 guests. It features a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a garden, and parking. Guests can also enjoy the homey atmosphere with a fireplace, board games, and a claw foot tub, as well as a tranquil porch and thoughtful amenities like complimentary snacks, beverages, books, bath salts, and bath bombs.

About: This modern and private apartment is conveniently located in East Orlando, just 20-30 minutes from major theme parks and attractions and 6 miles from downtown Orlando. It has excellent user, location, and cleanliness ratings. The apartment has 1 bedroom, 1 bathroom, and a floor area of 320 square feet. It can accommodate up to 2 guests. It features a fully equipped kitchen, a 58-inch flat-screen Roku TV, air conditioning, a garden, a spa, parking, and internet.

About: This Winter Park accommodation is the perfect retreat for travelers seeking comfort and convenience. Situated within walking distance to restaurants and 7-Eleven, it offers easy access to the area's vibrant dining scene and essential amenities. With excellent user, location, and cleanliness ratings, guests can expect a highly rated stay.

The accommodation features a private entrance with a hidden garden/patio, a well-equipped kitchen, a queen-sized pull-out couch in the living room, a 55-inch TV, a private bathroom overlooking the hidden garden/patio, and accommodates up to 4 guests. It's also close to major tourist attractions in Winter Park and provides a smoke-free environment for a comfortable and enjoyable stay.

About: This downtown Orlando accommodation is a 2-bedroom apartment with a spacious porch and a convenient kitchenette. It's within walking distance of major attractions like the Dr. Phillips Center and Amway Arena, and has an excellent user rating for its central location, cleanliness, and amenities.

The 700-square-foot apartment has one bathroom and can accommodate up to four guests. It comes with free parking, air conditioning, a garden, and enhanced cleaning measures. Guests can enjoy Netflix, Amazon Prime, and a digital antenna for entertainment, and the nearby Publix grocery store and Lake Eola provide additional convenience.

About: This studio apartment is located in Orlando's Ivanhoe Village, known for its lively atmosphere and within walking distance to popular attractions and amenities, including the Science Center, Museum of Art, and Lake Ivanhoe. With excellent user, location, and cleanliness ratings, this studio offers a comfortable stay for two guests.

The loft-style studio features modern appliances and furnishings, keyless entry for convenient self-check-in, and a spacious layout with high ceilings and exposed beams. Guests can enjoy amenities such as a fully equipped kitchen with a fridge and microwave, air conditioning, parking, and proximity to entertainment options, outdoor recreation, and cultural attractions.

About: This centrally located 2-bedroom apartment in Winter Park is within walking distance of charming Park Avenue and a short drive from downtown Orlando. With excellent user, location, and cleanliness ratings, this fully furnished apartment is perfect for up to 5 guests.

The apartment features a fully stocked kitchen, private parking, and a garden, ensuring a comfortable and enjoyable stay. Guests can also take advantage of the proximity to Rollins College, the Charles Hosmer Morse Museum of American Art, and the Winter Park Farmers' Market, all within walking distance or a short drive.

About: This Winter Park apartment is situated in a prime location, steps from Park Avenue and within walking distance of restaurants, shops, art galleries, and Rollins College. The apartment has received excellent ratings for its location, cleanliness, and user experience.

The apartment features a spacious layout with 3 bedrooms and 2 bathrooms, accommodating up to 6 guests. It boasts a fully equipped kitchen, comfortable furnishings, and a private outdoor space. Guests can enjoy amenities such as air conditioning, internet, and dedicated parking.

About: This Altamonte Springs guest suite is a private and separate entrance accommodation within walking distance of Altamonte Mall and a short drive from Disney Area Attractions and the Atlantic Coast. Guests have rated this accommodation as excellent in terms of location, cleanliness, and overall user experience.

The suite features a stylish interior design with a four-post queen shutter style bed, a wet bar area with a mini-fridge, a morning coffee bar, and a full bathroom with a shower. It can accommodate up to 2 guests and offers amenities such as air conditioning, internet access, a garden, and parking.

About: This luxurious accommodation is situated in Spring Valley, Altamonte Springs, offering easy access to nearby theme parks and beaches. It has received excellent ratings for its location, cleanliness, and user experience.

The accommodation features a private entrance and bathroom, a breakfast kitchenette, and a layout with one bedroom and one bathroom, accommodating up to two guests. Amenities include a swimming pool, garden, air conditioning, internet, fridge, freezer, and microwave oven. Guests can enjoy activities like canoeing, sunbathing, and relaxation in the peaceful neighborhood with mature oak trees and ample shopping and award-winning restaurants nearby.

About: This centrally located condo in Winter Park is within walking distance of Park Avenue shops and restaurants and a short drive to downtown Orlando. The apartment has excellent user, location, and cleanliness ratings.

The 2-bedroom, 2-bathroom condo has a split floor plan and can accommodate up to 5 guests. The fully equipped kitchen includes a washer and dryer. The open concept living and dining area has an abundance of natural light. The enclosed porch and private outdoor patio are perfect for relaxation. Two parking spaces are directly in front of the unit.

About: This one-bedroom, one-bathroom vacation home in Orlando's charming College Park district is a great choice for couples or small families. It's within walking distance of Dubsdread Golf Course and Lee Road Shopping Center, and a short drive from Loch Haven Park and Mead Garden. The home has a fully equipped kitchen, a patio, and a TV with a DVD player. It also has a water park and a garden, providing entertainment and relaxation for guests.

The house has received excellent user ratings, with guests praising its cleanliness, comfort, and convenient location. It's a great option for those looking for a comfortable and affordable place to stay in Orlando.

About: This studio apartment is located in the heart of Downtown Orlando, overlooking the pool and lake with views of the city skyline, just steps from Lake Eola Park and a short drive from major tourist attractions. It has excellent user, location, and cleanliness ratings. The studio has a private entrance, 1 bedroom, 1 bathroom, and a guest capacity of 2. It features a wetbar with a microwave, mini-fridge, and coffee maker, as well as a 65" TV with access to streaming services and live TV. Guests can enjoy a private outdoor shower, dock with canoe, and access to a shared pool and spa.

About: This apartment is located in College Park, a quiet neighborhood just a short drive from Dubsdread Golf Course and AdventHealth Orlando. It has received excellent ratings for its location, cleanliness, and overall experience.

The apartment features a spacious layout with 430 square feet of living space, one bedroom, one bathroom, and a guest capacity of two. It offers a fully equipped kitchen, a private pool, a patio, and access to a water park, outdoor pool, and spa tub. Guests can also enjoy a garden area and proximity to local attractions.

About: This vacation home is located in Maitland, within a 3-mile radius of Lake Lily Park, Altamonte Mall, and The Center of Winter Park Shopping Center. The house has an excellent user rating.

The house has 5 bedrooms, 4 bathrooms, and a floor area of 2800 square feet. It can accommodate up to 8 guests. The house has a private pool, a fireplace, a kitchen with a refrigerator, oven, stovetop, and microwave, and a washing machine. Guests can also enjoy the outdoor pool, garden, and barbecue grills. Housekeeping is available on request.

About: This vacation home in College Park, Orlando, is close to Dubsdread Golf Course, Kia Center, Camping World Stadium, AdventHealth Orlando, and Loch Haven Park. It has excellent user, location, and cleanliness ratings.

With a floor area of 300 square feet, this 1-bedroom, 1-bathroom house can accommodate up to 2 guests. It features a kitchen with a fridge, freezer, and microwave oven, as well as a private pool, outdoor pool and spa tub, kitchenette, balcony, garden, and access to a water park.

About: **Goldenrod House**

This luxurious guesthouse is conveniently located in downtown Winter Park, approximately 10 minutes from Rollins College/Full Sail and UCF, with easy access to the 417 expressway. It has excellent user, location, and cleanliness ratings. The house has 2 queen bedrooms, 2 bathrooms, and can accommodate up to 6 guests.

The house offers a private oasis with a secluded guesthouse on the same property as the main house, providing privacy and tranquility. It features a saltwater pool and hot tub, outdoor games, built-in grill, and a fully equipped kitchen with Breville espresso machine and Keurig.

About: This 2-bedroom, 2-bathroom condo is located in the Ventura Country Club neighborhood of Orlando, just 6 miles from Orlando International Airport and within 20-30 minutes of Disney World, SeaWorld, and Universal Studios. It has an excellent user rating.

The condo has a floor area of 850 square feet and can accommodate up to 6 guests. It features a fully equipped kitchen, three flat-screen TVs, a private screened patio, a washer and dryer, high-speed internet, and free local and long-distance telephone service in the US. Guests can also enjoy access to a swimming pool, Jacuzzi, terrace, balcony, garden, and parking.

About: This extravagant high-rise apartment is situated in the heart of downtown Orlando, offering stunning views and numerous amenities. Within walking distance of Lake Eola, clubs, bars, and restaurants, this apartment is highly rated for its prime location, cleanliness, and comfort.

The apartment features one bedroom and one bathroom, with a guest capacity of two. It includes a fully equipped kitchen, air conditioning, and access to a swimming pool, garden, spa, fitness center, and parking. The rooftop amenities include a pool, deck, grill, lounge area, and 24-hour gym.

About: This 3-bedroom, 2-bathroom apartment in the Dixie Belle neighborhood of Orlando is just 10 minutes from downtown and the International Airport. It has an excellent user rating and is family-friendly, with amenities like a swimming pool, garden, and spa.

The apartment has a private split floorplan with outdoor pool access and privacy. It has a custom-designed kitchen backsplash, custom bathrooms, and 43" smart TVs in all rooms. It also has a fully equipped kitchen, washer/dryer, easy access to private parking, and a code deadbolt for easy entry. It is pet-friendly and has internet access. The apartment is in a safe and secure location with cameras on the property for guest and property safety.

About: This apartment is located in the lively South Orange district of Orlando, within walking distance of major attractions and landmarks. With a "very good" user rating, this one-bedroom, one-bathroom apartment can accommodate up to four guests.

The apartment features a fully equipped kitchen, a Smart TV, and a cozy sofa bed. Guests can enjoy the water park within the apartment building complex or relax on the terrace/balcony. Parking is also available.

About: Situated on the tranquil shores of Lake Osceola, this apartment is just a short stroll from Rollins College, the Morse Museum of American Art, and the Albin Polasek Museum and Sculpture Gardens. It offers a perfect blend of tranquility and convenience, with excellent user ratings.

This family-friendly condo spans 1100 square feet and features two bedrooms, two bathrooms, and a private balcony. It can accommodate up to five guests comfortably. The fully equipped kitchen includes a refrigerator, microwave, and dishwasher, while the living area boasts a cozy fireplace. Guests can enjoy access to a swimming pool, terrace, garden, spa, and parking.

About: This Colonialtown South apartment offers visitors easy access to Orlando's attractions, with The Plaza Theatre just a 0.4 mi stroll away and Kia Center a short 2.5 mi drive. Highly rated by previous guests, this apartment boasts an excellent location in a charming district renowned for its historic architecture, delightful eateries, and unique shopping experiences.

Inside, the apartment provides a comfortable layout with a well-equipped kitchen featuring a microwave and dishwasher. Guests can enjoy amenities like a sparkling swimming pool, rejuvenating Jacuzzi, and state-of-the-art fitness center, ensuring a relaxing and active stay. Additionally, conveniences such as Wi-Fi, parking, and a washing machine add to the comfort and practicality of this apartment, making it an ideal choice for both short and extended stays in the captivating city of Orlando.

About: In the heart of Winter Park, this centrally located vacation home is surrounded by major tourist attractions and landmarks, including the Kraft Azalea Gardens, Winter Park Country Club, and Winter Park Village. With an excellent user rating, this two-bedroom, one-bathroom home accommodates up to four guests.

The vacation home features a fully equipped kitchen, air conditioning, a terrace or balcony, a garden, and parking. Guests can also enjoy free WiFi throughout the property.

About: This two-bedroom condo in Goldenrod is conveniently located near Full Sail University and Rollins College, and within driving distance of popular tourist destinations. With excellent user, location, and cleanliness ratings, this studio is a great choice for families or small groups looking for a comfortable and convenient stay.

The spacious two-bedroom layout can accommodate up to 4 guests and includes a fully equipped kitchen, living room with TV, and bedrooms with comfortable bedding. Guests will also enjoy amenities such as a private patio, laundry facilities, air conditioning, a swimming pool, and a garden. Additionally, the studio offers two parking spaces and is close to major tourist destinations, making it an ideal choice for travelers visiting Goldenrod.

About: This waterfront vacation home in Orlando is just 1 mile from Tinker Field and Camping World Stadium, and 1.4 miles from Kia Center. It features a private dock, as well as proximity to major tourist attractions. With excellent user and location ratings, this two-bedroom, one-bathroom home accommodates up to four guests in 450 square feet of space.

It includes a fully equipped kitchen, free WiFi, a sofa bed, and a private outdoor space with a patio or balcony. Guests can enjoy a water park, garden, barbecue grills, a smoke-free environment, and pet-friendly accommodation.

About: This family-friendly vacation home in Winter Park is just 2.2 miles from Full Sail University and within 6 miles of popular attractions like Kraft Azalea Gardens and the University of Central Florida. It has excellent user, location, and cleanliness ratings.

The house has 3 bedrooms, 2 bathrooms, and 1400 square feet of floor area. It features a private, fenced yard, a fireplace, water park access, barbecue grills, a fully equipped kitchen, free WiFi, and a smoke-free environment.

About: This Altamonte Springs vacation home is conveniently located in the city center, within a short distance of popular attractions like Altamonte Mall and Cranes Roost Park. With excellent user, location, and cleanliness ratings, this house offers a comfortable and well-maintained stay for travelers.

The house features three bedrooms, two bathrooms, and a floor area of 2200 square feet, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, free Wi-Fi, air conditioning, a private fenced yard, and parking. Guests can also enjoy games and entertainment options within the non-smoking environment.

About: This apartment is located in Lake Eola Heights, just a short walk from Lake Eola and other popular attractions. Guests have consistently rated this apartment very highly for its cleanliness, location, and overall experience.

The apartment has one bedroom and one bathroom, and can accommodate up to four guests. It has a fully equipped kitchen, a living room with a sofa bed, and a balcony. The apartment also has air conditioning, free Wi-Fi, and free parking. Guests can enjoy a variety of activities in the area, such as swimming, biking, and fishing.

About: This two-bedroom condo is situated in the lively Colonialtown South district, known for its charming shops, restaurants, and nightlife. It is within walking distance to Lake Eola Park and a short drive from major attractions like Kia Center and Camping World Stadium.

The apartment has an excellent user rating, location rating, and cleanliness rating. It has a floor area of 790 square feet and can accommodate up to 5 guests. It features a fully equipped kitchen, free WiFi, a sofa bed, access to a water park, self-parking, and a garden within the condo building.

About: This golf apartment building is situated in the peaceful Ventura neighborhood, just 0.1 mi (0.1 km) from Ventura Country Club and within 6 mi (10 km) of Lake Conway and Rio Pinar Country Club. It has very good user and location ratings.

The apartment features a private balcony, a fully equipped kitchen with modern appliances, and access to a water park, outdoor pool, fitness center, and spa tub. Barbecue grills are also available for outdoor cooking and entertainment.

About: This 1-bedroom, 1-bathroom condo in Winter Park is just steps from Park Avenue, the city's renowned shopping, dining, and cultural hub. With excellent user, location, and cleanliness ratings, this pet-friendly condo offers a comfortable and convenient stay for up to three guests.

The condo features a fully equipped kitchen, laundry facilities, high-speed internet, air conditioning, a swimming pool, a Jacuzzi, a garden, and parking. It's also close to Lake Baldwin Park and numerous hiking and biking trails, offering opportunities for outdoor activities.

About: This private and newly remodeled guest suite is centrally located near Downtown Orlando, within walking distance of restaurants, shopping, and parks. It is a safe and family-friendly neighborhood with easy access to Downtown Orlando, Theme Parks, and Winter Park/Park Ave.

This pet-friendly accommodation has excellent user, location, and cleanliness ratings. It has one bedroom, one bathroom, and a guest capacity of two. It features a full kitchen, spacious living area, luxurious queen bed, flat-screen smart TV with Netflix, air conditioning, swimming pool, garden, and parking. Guests can enjoy convenient self check-in and a private 2nd story entrance.

About: This hidden tiny cottage is located in Longwood, on the back side of the property on Beach Avenue. It has excellent user, location, and cleanliness ratings.

The cottage has one bedroom, one bathroom, and a floor area of 600 square feet. It can accommodate up to two guests. It is a unique and tranquil getaway with a cozy and cute brand new interior. It has a kitchenette, a sofa that converts into a bed for extra guests, a new AC window unit for comfort, and an outdoor chair and fire pit for warmth and enjoyment. It is perfect for visitors or those needing a break from the hustle and bustle.

About: This well-appointed condo in Winter Park is a perfect home base for your next vacation. It is conveniently located just steps from Park Avenue and Lake Virginia, with a jogging trail. The condo has a split floor plan with two bedrooms and two bathrooms located on opposite sides of the living area for privacy.

In addition to the well-equipped kitchen, the condo also has a separate dining room, an enclosed porch, and an additional private patio. It also has access to a pool and fitness center.

About: This centrally located apartment in Winter Park provides easy access to the city's attractions, shops, and restaurants, all within walking distance. It has received excellent user ratings, highlighting its quality and appeal among guests.

The apartment features two bedrooms, two bathrooms, and over 1200 square feet of living space, comfortably accommodating up to eight guests. It offers a fully equipped kitchen, ample storage, a private entrance, and modern furnishings. Guests also have access to convenient parking and amenities such as air conditioning, internet, and pet-friendly accommodations.