Vacation Rentals in Winter Park, FL

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

Top-Rated Family-Friendly Holiday Rentals in Winter Park, FL

Find family holiday rentals in Winter Park, FL with space and comfort for the whole crew.

7.3miles To Airport + 20miles To Disney + 8.2miles To Dt! - Winter Park, FL
8.6 11 reviews

7.3miles To Airport + 20miles To Disney + 8.2miles To Dt!

apartment, Orlando
This house is located in Orlando, just 800 metres from Ventura Country Club and within 10 kilometres of several shopping centres, offering a peaceful retreat close to amenities. It has received excellent user ratings, making it a popular choice for travellers.
The property features three bedrooms, two bathrooms, and can accommodate up to 10 guests. The house is equipped with a fully fitted kitchen, air conditioning, a terrace, a garden, and parking, providing everything you need for a comfortable stay.
Orlando Oasis! Free Laundry & Parking Near Disney! - Winter Park, FL
9.3 41 reviews

Orlando Oasis! Free Laundry & Parking Near Disney!

house, Orlando
This Orlando holiday home is located just 4.5km from Church Street Station and 4.7km from Amway Center, offering easy access to the city's main attractions. It has received excellent ratings for location, cleanliness, and overall experience.
The property has three bedrooms, one bathroom, and spans 102 square metres, comfortably accommodating up to eight guests. Guests can enjoy modern amenities including air conditioning, free Wi-Fi, a fully equipped kitchen, and a garden with an outdoor fireplace and barbecue facilities.
3-bedroom House In Quaint Winter Park With Cool Vibes - Winter Park, FL
No reviews

3-bedroom House In Quaint Winter Park With Cool Vibes

apartment, Winter Park
This three-bedroom, two-bathroom holiday home in Winter Park's Hannibal Square is conveniently situated 720 metres from the Morse Museum of American Art and 880 metres from the Casa Feliz Historic Home Museum, with Winter Park Station a 10-minute walk away.
This family-friendly apartment offers Wi-Fi, air conditioning, a full kitchen, laundry facilities, and a garden, accommodating up to seven guests for a comfortable stay near local attractions and a golf course.
Luxury Tiny Home 2 Miles From Downtown Orlando - Winter Park, FL
9.6 195 reviews

Luxury Tiny Home 2 Miles From Downtown Orlando

B&B, Orlando
This charming bed and breakfast is located just 3.2 kilometres from Orlando's city centre, offering easy access to attractions like Church Street Station, Amway Center, and Camping World Stadium. The property has consistently received excellent ratings for cleanliness, location, and guest satisfaction.
The cosy guesthouse features a single bedroom and bathroom, spanning a total of 9 square metres. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, a garden, and free Wi-Fi, making it a comfortable and convenient choice for travellers.

Best Winter Park, FL holiday rentals with parking

Winter Park Guest Suite |Near Ucf/fullsail/rollins - Winter Park, FL
9.8 111 reviews

Winter Park Guest Suite |Near Ucf/fullsail/rollins

apartment, Goldenrod
This charming guesthouse is situated in a central Winter Park neighbourhood, just a short drive from UCF, Rollins College, Full Sail, and Park Avenue. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The self-contained suite is attached to the main house but has its own private entrance, accommodating up to two guests. The suite includes a fully equipped kitchen with a fridge, freezer, microwave, and cooktop, as well as air conditioning and parking.
Modern Luxury King Suite | Central Orlando + Pool - Winter Park, FL
10 35 reviews

Modern Luxury King Suite | Central Orlando + Pool

apartment, Orlando
This modern one-bedroom apartment in Orlando, Florida, is conveniently located 8 kilometres from Universal Studios, 43 kilometres from Walt Disney World, and 27 kilometres from the new Epic Universe, with downtown Orlando attractions such as Lake Eola and the Dr. Phillips Centre just 800 metres away.
This pet-friendly accommodation for up to four guests offers resort-style amenities including a swimming pool, fitness centre, fully-equipped kitchen with stainless steel appliances, a queen-size sofa bed, a king-size bed in the master bedroom, and in-unit laundry facilities.
Modern, Charming Home In The Heart Of Winter Park- Perfect For A Couples Retreat Or Small Group! - Winter Park, FL
9.8 18 reviews

Modern, Charming Home In The Heart Of Winter Park- Perfect For A Couples Retreat Or Small Group!

apartment, Winter Park
This Winter Park house, near Park Avenue, Rollins College, and Winter Park Village, offers easy access to AdventHealth Winter Park (under 2 km), Rollins College and Park Avenue (around 8 km), and Winter Park Village (approximately 12 km).
The 1100 square metre property boasts three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen with stainless steel appliances, a garden, parking, and Wi-Fi; nearby attractions include the Morse Museum and Dr. Phillips Center for the Performing Arts.
Thornton Park Oasis 1 Bedroom - Winter Park, FL
10 1 review

Thornton Park Oasis 1 Bedroom

apartment, Orlando
This one-bedroom flat in Orlando's Thornton Park district is located 0.7 kilometres from the city centre, 1.9 kilometres from the Kia Centre, and 4 kilometres from Camping World Stadium, with Church Street Station a 19-minute walk away.
This 70 square metre apartment accommodates up to three guests and features complimentary WiFi, air conditioning, a private patio, and a fully equipped kitchen with a fridge and microwave oven.

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.

Popular destinations

Popular Holiday Rentals with a Terrace in Winter Park, FL

Check the weather and enjoy the fresh breeze right outside your door at holiday rentals with a balcony in Winter Park, FL.

Adorable 1-bedroom Home W/ Full Kitchen & Parking - Sleeps 4 - Winter Park, FL
9.4 16 reviews

Adorable 1-bedroom Home W/ Full Kitchen & Parking - Sleeps 4

apartment, Orlando
This one-bedroom apartment is located in Colonialtown South, just 800 metres from Lake Eola and within 5 kilometres of the Kia Center and Camping World Stadium. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 73 square metres and includes a fully equipped kitchen, a terrace, and a garden. It also offers amenities like free Wi-Fi, parking, air conditioning, and a designated smoking area, making it a comfortable and convenient base for exploring Orlando.
Comfy Studio In Central Orlando - Winter Park, FL
8.0 1 review

Comfy Studio In Central Orlando

studio, Azalea Park
This Azalea Park flat is centrally located, offering convenient access to Orlando's major theme parks and attractions, with Universal Studios 13.9 kilometres away, Aquatica 18.2 kilometres, SeaWorld 18.5 kilometres, and Disney World 21.1 kilometres.
This newly remodelled studio, accommodating two guests, features a queen-size memory foam bed, a Smart TV, a kitchenette with a microwave oven, complimentary Wi-Fi, air conditioning, a shared garden with outdoor seating, and free parking for one vehicle.
Apartment ∙ 2 Bedrooms ∙ 4 Guests - Winter Park, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Orlando
This 2-bedroom, 2-bathroom condo is located in the gated Ventura Golf Resort, 16 kilometres from Orlando International Airport (MCO) and within easy reach of major theme parks, being 24 kilometres from Walt Disney World and 40 kilometres from Universal Studios.
This family-friendly holiday apartment offers accommodation for up to four guests, featuring a private balcony, central air conditioning, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, and access to resort amenities including a swimming pool, gym, and various sports courts.
Condo With Pool, Gym, Golf, Jacuzzi And Game Areas - Winter Park, FL
No reviews

Condo With Pool, Gym, Golf, Jacuzzi And Game Areas

house, Orlando
This apartment is located approximately 8 kilometres from Church Street Station, 8.6 kilometres from the Kia Centre, and 8 kilometres from Orlando International Airport.
This property offers 63 square metres of living space, accommodating up to seven guests with one bathroom, a fully equipped kitchen, complimentary WiFi, air conditioning, a swimming pool, jacuzzi, balcony, garden, and on-site fitness centre.

Popular Dog-Friendly Holiday Rentals in Winter Park, FL

Browse pet-friendly holiday rentals in Winter Park, FL where dogs are always welcome.

Laid Back & Private In Lovely Winter Park Orlando - Winter Park, FL
9.6 5 reviews

Laid Back & Private In Lovely Winter Park Orlando

apartment, Winter Park
This Winter Park flat is located adjacent to the Interlachen Country Club, a 5-minute drive from Lake Howell Plaza and the shops and restaurants of Park Avenue.
This one-bedroom flat accommodates up to four guests and offers parking, internet, air conditioning, and a kitchen, with Universal Orlando Resort 25-35 minutes away and Walt Disney World 35-45 minutes away.
Charming 3-bedroom Near Orlando Theme Parks, Downtown And Golf Courses - Winter Park, FL
9.8 20 reviews

Charming 3-bedroom Near Orlando Theme Parks, Downtown And Golf Courses

apartment, Casselberry
This recently renovated three-bedroom, two-bathroom flat in Casselberry, Seminole County, offers convenient access to Orlando's theme parks (40 kilometres), downtown Orlando (32 kilometres), Wekiva Springs State Park (32 kilometres), and coastal destinations including Coco Beach and NASA (64 kilometres).
This 172-square-meter accommodation, suitable for up to six guests, includes a fully equipped kitchen with a microwave and dishwasher, air conditioning, Wi-Fi, a washer/dryer, and private parking, with local shopping and entertainment venues within walking distance.
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow - Winter Park, FL
9.4 235 reviews

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

apartment, Goldenrod
This Goldenrod holiday home is located just 2.2 kilometres from Full Sail University, and within a 10-kilometre radius of the University of Central Florida, Albin Polasek Museum and Sculpture Gardens, Rollins College, and Kraft Azalea Gardens. The property has received excellent ratings for location, cleanliness and user experience.
The house has three bedrooms and two bathrooms, accommodating up to six guests. Amenities include a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, a garden, parking, and internet access.
Stylish 2br Home W/ Private Entrance - Winter Park, FL
No reviews

Stylish 2br Home W/ Private Entrance

house, Orlando
This detached house in Orlando's College Park district offers a historic feel and is situated 4 kilometres from Winter Park Village and 8 kilometres from downtown Orlando's Amway Center and Camping World Stadium.
This family-friendly, pet-welcoming property sleeps up to four guests in two bedrooms, featuring a full kitchen, air conditioning, on-site parking, and a washer/dryer, with Disney World and Universal Studios approximately 32 kilometres away.
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