Vacation Rentals in Winter Park, FL

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Winter Park, FL holiday rentals
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288 Holiday rentals and Airbnb in Winter Park, FL

Best family friendly Winter Park, FL holiday rentals

Among the 288 accommodations in Winter Park, FL, here are the 4 best family friendly rentals

Stylish Boutique Guest House In Winter Park - Winter Park, FL
10 109 reviews
Winter Park, FL
28/06 – 18/07
A$250/nighttotal: A$5000 (20 )

Stylish Boutique Guest House In Winter Park

3 1
apartment , Winter Park
This two-bedroom flat is ideally located in Winter Park, just a short distance from attractions like the Casa Feliz Historic Home Museum and the Morse Museum of American Art. It has received excellent reviews from previous guests.
The apartment comfortably sleeps four guests and features a fully equipped kitchen, a fireplace, and a balcony. Guests can enjoy the on-site fitness centre, swimming pool, and garden, as well as free Wi-Fi and parking.
Villa With Guest House & Pool-patio - Winter Park, FL
9.9 130 reviews
Winter Park, FL
10/07 – 18/07
A$518/nighttotal: A$4144 (8 )

Villa With Guest House & Pool-patio

1 4
apartment , Casselberry
This holiday home is located in Casselberry, Florida, just a short drive from the attractions of Orlando, approximately 30 kilometres away. The accommodation has received excellent ratings for location, cleanliness, and user experience.
The property offers 4 bedrooms and 2 bathrooms, comfortably accommodating up to 8 guests, with an optional guest house for additional space. Guests can enjoy a fully equipped kitchen, a private pool and garden, a Jacuzzi, and a covered garage with ample parking space.
Orlando Oasis: Private Pool Home - Winter Park, FL
Winter Park, FL
28/06 – 18/07
A$707/nighttotal: A$14140 (20 )

Orlando Oasis: Private Pool Home

2 1
apartment , Holden Heights
This two-bedroom apartment in Holden Heights is located just a short distance from Orlando city centre, making it a convenient base for exploring the area's many attractions, including Florida Mall and Universal Orlando Resort, both within 10km. The apartment is situated on a tranquil lake, offering a peaceful escape from the hustle and bustle of the city.
The apartment has an open-plan layout, perfect for families or groups of up to five guests. The apartment offers a range of amenities, including a swimming pool, a private garden and a spa, ensuring a comfortable and enjoyable stay.
Modern 2br Near Park Ave Perfect For Groups - Winter Park, FL
10 19 reviews
Winter Park, FL
28/07 – 01/08
A$269/nighttotal: A$1076 (4 )

Modern 2br Near Park Ave Perfect For Groups

1 2
apartment , Goldenrod
This two-bedroom flat is located in a quiet residential district of Goldenrod, just 500 meters from Park Avenue's shops and restaurants, and a short drive from Rollins College and Full Sail University.
The property accommodates up to six guests and offers a fully equipped kitchen, air conditioning, a garden, private parking for four cars, and a dedicated workspace with Wi-Fi, ideal for those seeking a convenient stay.

Best Winter Park, FL holiday rentals with parking

Paradise Apartment - Winter Park, FL
9.5 8 reviews
Winter Park, FL
28/07 – 01/08
A$228/nighttotal: A$912 (4 )

Paradise Apartment

2 2
apartment , Winter Park
This Orlando flat is situated approximately 12.9 kilometres from downtown attractions such as Church Street Station and Spectrum Stadium, and around 12.7 kilometres from Addition Financial Arena.
This property offers two bathrooms, accommodates eleven guests, and boasts a floor area of 7 square metres, complete with air conditioning, a kitchen, WiFi, a swimming pool, a garden, barbecue facilities, and a sun terrace.
3bdrm Fruit Tree Home Near Downtown Orlando - Winter Park, FL
9.0 22 reviews
Winter Park, FL
28/06 – 18/07
A$308/nighttotal: A$6160 (20 )

3bdrm Fruit Tree Home Near Downtown Orlando

3 1
apartment , Orlando
This Orlando home is located just 1.1 km from Grand Avenue Park and within 5 km of Kia Center and Camping World Stadium, making it a convenient base for exploring the city's attractions. It has received excellent user ratings, so you can be sure of a comfortable stay.
The property has 3 bedrooms and can accommodate up to 8 guests, making it suitable for families or groups of friends. The house offers a range of amenities, including a swimming pool, jacuzzi, garden, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Downtown Zen. Perfect Location To Explore Downtown Orl. Private 1 Bedroom House - Winter Park, FL
10 45 reviews
Winter Park, FL
28/06 – 18/07
A$390/nighttotal: A$7800 (20 )

Downtown Zen. Perfect Location To Explore Downtown Orl. Private 1 Bedroom House

1 1
apartment , Orlando
This charming house is located in Colonialtown South, a short distance from The Plaza Theatre (0.6km) and Kia Center (4km), offering a peaceful retreat in a historic neighbourhood. The property has consistently received excellent user ratings, making it a popular choice for travellers.
The house features a fully equipped kitchen, a private pool, and a garden, providing everything you need for a comfortable stay. You can also enjoy the fitness centre, the terrace, and the jacuzzi, as well as the family-friendly amenities like the arcade room and the fenced yard.
Cute Guest House In Winter Park Minutes From Downtown In Car - Winter Park, FL
9.6 307 reviews
Winter Park, FL
28/06 – 18/07
A$211/nighttotal: A$4220 (20 )

Cute Guest House In Winter Park Minutes From Downtown In Car

1 1
apartment , Fairview Shores
This charming studio apartment is situated just a short drive from the Park Ave strip and Winter Park Village, offering easy access to shopping, dining, and entertainment. Guests consistently rate the property excellent for its location, cleanliness, and overall experience.
The studio is compact and comfortable, measuring 30 square metres and accommodating up to two guests. It includes modern amenities such as a kitchenette, refrigerator, air conditioning, smart TV, Wi-Fi internet, a queen-size bed, and a private bathroom with complimentary toiletries.

Frequently asked questions about holiday rentals in Winter Park, FL

  • What should a first-time visitor not miss in Winter Park, FL?

    Winter Park is a charming city, and a first-timer should definitely visit the scenic Rollins College, stroll along Park Avenue, and enjoy a boat ride on the charming Winter Park Chain of Lakes. It's a great way to get a feel for the city's history and beautiful surroundings.
  • What are the best Airbnb and holiday rentals in Winter Park, FL?

    Modern Tropical Pool Home , Upscale Loft Space Close To Downtown and Moniker Manor (Entire Home Near Downtown) are among the best Airbnb and holiday rentals in Winter Park, FL.

  • Which neighborhood in Winter Park, FL should you consider for a vacation rental?

    For a vacation rental, you might want to consider the area around Park Avenue. It's a bustling hub with lots of shops, restaurants, and things to do, but it's also very walkable and has a lovely, historic feel. The area around the Winter Park Chain of Lakes is also great for a more relaxed vibe, with plenty of nature and outdoor activities.
  • What are the most popular Airbnbs in Winter Park, FL?

  • What are the top family-friendly attractions in Winter Park, FL?

    Winter Park has plenty to offer families. The Charles Hosmer Morse Museum of American Art is a great place to visit, and the kids will love the interactive exhibits at the Orlando Science Center. For a bit of outdoor fun, head to the Mead Garden, a beautiful botanical garden with a playground, or the Winter Park Farmers' Market, where you can find local produce and crafts.
  • What are the best holiday rentals with a pool in Winter Park, FL?

  • When is the best time to book a vacation rental in Winter Park, FL?

    The best time to book a vacation rental in Winter Park depends on your preferences. If you want to avoid the crowds and enjoy cooler weather, the shoulder seasons of spring and autumn are ideal. If you're looking for sunshine and warmer temperatures, then summer is the time to go. Just remember to book well in advance, especially during peak season.
  • What are the best rentals for families and kids in Winter Park, FL?

  • What events or festivals should visitors check out in and around Winter Park, FL?

    Winter Park has a vibrant events calendar. The Winter Park Sidewalk Art Festival is a must-see, showcasing local artists and their work. The annual Winter Park Autumn Festival features live music, food stalls, and family-friendly activities. And don't miss the Winter Park Concours d'Elegance, a classic car show that attracts enthusiasts from all over.
  • What are the best rentals or Airbnbs with a jacuzzi in Winter Park, FL?

  • What are the best budget-friendly activities in Winter Park, FL?

    Winter Park has a lot to offer even on a budget. You can enjoy a free walk or bike ride around the Winter Park Chain of Lakes, visit the free exhibits at the Albin Polasek Museum & Sculpture Gardens, or relax and people-watch at the Winter Park Farmers' Market.
  • What are the best restaurants with local dishes in Winter Park, FL?

    For a taste of local flavour, try the seafood at The Boathouse, a classic Winter Park restaurant with stunning views of the lake. If you're looking for something a bit more casual, head to The Wine Bar, a popular spot for tapas and small plates. Both offer great menus with local ingredients.
  • What are the best walking or cycling routes in Winter Park, FL?

    The Winter Park Chain of Lakes is a beautiful place for a walk or bike ride. You can follow the paved trails around the lakes, enjoying the scenery and the fresh air. If you're looking for a longer ride, try the West Orange Trail, a 21 km paved trail that runs through Winter Park and beyond.
  • Are there pet-friendly attractions in Winter Park, FL?

    Winter Park is very dog-friendly. The Winter Park Chain of Lakes is great for a walk with your furry friend, and many restaurants and cafes have outdoor seating where you can enjoy a meal with your pet. You can also visit the Mead Garden, which has a designated dog-walking area.
  • What are the benefits of choosing a vacation rental in Winter Park, FL?

    Vacation rentals offer a more spacious and private experience compared to hotels. You can often find rentals with unique features like private pools or hot tubs, providing a more comfortable and relaxing stay. Plus, you have the flexibility to cook your own meals and enjoy the comforts of home.
  • What are the top sports attractions and facilities in Winter Park, FL?

    Winter Park is home to the Winter Park Racquet Club, a popular destination for tennis enthusiasts. The club offers both indoor and outdoor courts, along with a pro shop and a restaurant. For those who prefer a more relaxed pace, the Winter Park Chain of Lakes is a great place to enjoy a leisurely paddleboat or kayak ride.

Destinations nearby

Best Winter Park, FL holiday rentals with a balcony

Lovely Space In Downtown Orlando - Winter Park, FL
Winter Park, FL
28/06 – 18/07
A$344/nighttotal: A$6880 (20 )

Lovely Space In Downtown Orlando

2 1
apartment , Orlando
This **Orlando apartment** is located in Downtown Orlando, a 13-minute walk from Church Street Station and within 644 metres of the city centre.
This spacious **Orlando flat** offers 2 bedrooms, 2 bathrooms, accommodates up to 7 guests, and features a fully equipped kitchen, complimentary WiFi, air conditioning, and a private balcony, with a fitness centre available on-site.
Large, Beautiful, Very Comfortable One Bedroom On Small Lake - Winter Park, FL
9.9 226 reviews
Winter Park, FL
28/07 – 01/08
A$394/nighttotal: A$1576 (4 )

Large, Beautiful, Very Comfortable One Bedroom On Small Lake

1 2
apartment , Orlando
This family-friendly holiday home is located just under 2 kilometres from Lake Eola Park and its surrounding area, offering a peaceful escape from the hustle and bustle of downtown Orlando. The property has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom property spans 46 square metres and can comfortably accommodate two guests. The house is equipped with a fully-equipped kitchen, a private pool, a spa, a sauna, a gym, and a tennis court, providing plenty of opportunities for relaxation and entertainment.
Brand New Luxury Modern 5br/4.5ba+game Room Home - Winter Park, FL
10 6 reviews
Winter Park, FL
10/07 – 18/07
A$721/nighttotal: A$5768 (8 )

Brand New Luxury Modern 5br/4.5ba+game Room Home

5 4
apartment , Altamonte Springs
This Altamonte Springs flat is situated 39 kilometres from the Magic Kingdom and 29 kilometres from Universal Studios Florida, offering convenient access to major Orlando theme parks.
This spacious 307 square metre residence features five bedrooms, four bathrooms, and accommodates up to 15 guests with amenities including a fully equipped kitchen, a dedicated game room, and ample parking.
Lake Eola Thornton Park Studio With Balcony - Winter Park, FL
9.0 9 reviews
Winter Park, FL
28/07 – 01/08
A$204/nighttotal: A$816 (4 )

Lake Eola Thornton Park Studio With Balcony

1 2
studio , Orlando
This Thornton Park studio apartment is centrally located in Orlando, Florida, within walking distance of Lake Eola Park, the Amway Center, and the Dr. Philips Center for the Performing Arts.
The 65-square-metre self-contained apartment sleeps two guests and features a full kitchen, a private balcony, and free on-site parking; nearby attractions include easy access to the SunRail commuter rail and the free Lynx bus service.

Best pet friendly Winter Park, FL holiday rentals

Among the 288 accommodations in Winter Park, FL, here are the 4 best pet friendly rentals

Enjoy Your Stay In Our Cozy 2 Bedroom 1 Bath Guest Suite.newly Renovated Space - Winter Park, FL
10 1 review
Winter Park, FL
28/06 – 18/07
A$242/nighttotal: A$4840 (20 )

Enjoy Your Stay In Our Cozy 2 Bedroom 1 Bath Guest Suite.newly Renovated Space

2 1
apartment , Altamonte Springs
This Altamonte Springs flat is ideally situated, offering a 16-kilometre drive to downtown Orlando, a 32-kilometre journey to Orlando's theme parks, and a 56-kilometre route to the East Coast beaches, with Winter Park's dining and shopping readily accessible.
This two-bedroom flat accommodates up to four guests and features air conditioning, a swimming pool, a jacuzzi, and parking, with a kitchen equipped with a fridge, microwave oven, and dishwasher, and is located near Wekiwa Springs State Park and Rock Springs Run.
Charming Private Studio/full Amenities / Great Location - Winter Park, FL
Winter Park, FL
28/06 – 18/07
A$164/nighttotal: A$3280 (20 )

Charming Private Studio/full Amenities / Great Location

1 1
studio , Orlando
This one-bedroom apartment is located in a quiet industrial area on the edge of the Lake Baldwin district, offering convenient access to Downtown Orlando, the Kia Centre, and Orlando International Airport (MCO).
This private studio accommodates two guests and features air conditioning and internet, with immediate access to shops, restaurants, and proximity to Universal Orlando Resort and the Florida Mall.
Cozy 2bd 2bth House Walk To Local Gems - Winter Park, FL
9.2 7 reviews
Winter Park, FL
10/07 – 18/07
A$254/nighttotal: A$2032 (8 )

Cozy 2bd 2bth House Walk To Local Gems

2 4
house , Orlando
This Orlando house, situated 2.6km from the city centre and within 8km of Church Street Station, Camping World Stadium, and the Kia Center, offers convenient access to major attractions.
This two-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen with dishwasher, a terrace, garden, free Wi-Fi, and free private parking; enjoy al fresco dining and proximity to local amenities.
Cozy Apt With Pool, Hot Tub, Golf, Near Downtown - Winter Park, FL
Winter Park, FL
28/07 – 01/08
A$213/nighttotal: A$852 (4 )

Cozy Apt With Pool, Hot Tub, Golf, Near Downtown

2 2
house , Orlando
This Orlando dwelling is situated 8.05 kilometres from Church Street Station and 8.19 kilometres from the Kia Centre, with Orlando International Airport a mere 8.05 kilometres away.
This 76 square metre holiday home accommodates up to seven guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, hot tub, balcony, garden, fitness centre, and tennis courts, with free Wi-Fi provided.
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