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.

Winter Park Citrus Escape - Winter Park, FL
No reviews

Winter Park Citrus Escape

house, Goldenrod
This Goldenrod holiday home, situated in Orlando's Winter Park district, is approximately 13 kilometres from the Addition Financial Arena and Spectrum Stadium.
The 149-square-metre property boasts three bedrooms, two bathrooms, sleeps fifteen guests, and includes a private pool, free parking, and a fully equipped kitchen; free Wi-Fi and a washing machine add to its convenience.
Universal's Loews Portofino Bay Hotel - Winter Park, FL
9.1 1862 reviews

Universal's Loews Portofino Bay Hotel

resort, Orlando
Universal's Loews Portofino Bay Hotel is located in the Universal Orlando Resort area, close to CityWalk and within easy reach of Universal Studios and Islands of Adventure. The hotel has received very good user ratings, with an excellent location and cleanliness rating.
The hotel has an Italian-inspired design and offers a range of amenities including a spa, fitness centre, and complimentary transport to Universal Studios theme parks. Guests also benefit from exclusive unlimited ride access and early park admission to Universal's theme parks.
Bungalow On Quiet Street Close To Trendy Cafes, Pubs, And Parks. Dogs Welcome! - Winter Park, FL
10 44 reviews

Bungalow On Quiet Street Close To Trendy Cafes, Pubs, And Parks. Dogs Welcome!

apartment, Orlando
This Baldwin Park holiday home is situated within 5km of Orlando Fashion Square, East Orlando Shopping Centre, The Plaza Theatre, Harry P. Leu Gardens, and Lake Virginia.
This 102-square-metre property boasts two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, private fenced yard with patio and barbecue, plus free Wi-Fi.
Gojjo Retreat Backyard Guesthouse Walkable - Winter Park, FL
9.9 23 reviews

Gojjo Retreat Backyard Guesthouse Walkable

apartment, Orlando
This brand new 2025 luxury tiny home in Orlando offers a tranquil urban oasis, located within 500 meters of top dining establishments and close to the city's attractions.
This one-bedroom, one-bathroom flat accommodates up to four guests, featuring air conditioning, Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, plus off-street parking and a communal fire pit area.

Best Winter Park, FL holiday rentals with parking

2 Min To Park Ave | Charming Winter Park Bungalow - Winter Park, FL
9.8 88 reviews

2 Min To Park Ave | Charming Winter Park Bungalow

apartment, Fairview Shores
This apartment is located in Winter Park, a charming neighbourhood just 2 kilometres from Park Avenue and its diverse dining scene, and 40 kilometres from Orlando International Airport. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment can comfortably accommodate up to four guests and features a spacious and open layout. Guests can enjoy a peaceful outdoor patio, a well-equipped kitchen, air conditioning, a garden, a fitness centre, and parking.
Renovated College Park 3/2 Sleeps 10 Close To Wp - Winter Park, FL
9.3 217 reviews

Renovated College Park 3/2 Sleeps 10 Close To Wp

apartment, Fairview Shores
This newly renovated three-bedroom duplex, sleeping up to ten guests, is situated in north College Park, bordering Lake Fairview, approximately 13km from downtown Orlando and 32km from the theme parks.
The 111m² property boasts a fully equipped kitchen with dishwasher, multiple Roku TVs, a private fenced backyard, and step-free porch access; nearby attractions include College Park's restaurants and historic neighbourhoods.
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.
Enjoy Your Stay In Our Cozy 2 Bedroom 1 Bath Guest Suite.newly Renovated Space - Winter Park, FL
10 1 review

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

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.

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.

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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.

Orlando Tiny Home Near Kia Center W Free Parking - Winter Park, FL
9.2 5 reviews

Orlando Tiny Home Near Kia Center W Free Parking

apartment, Orlando
This modern one-bedroom apartment is located in the Lawsona - Fern Creek neighbourhood of Orlando, a short walk from Lake Eola and its surrounding restaurants and nightlife, and within 32 kilometres of the theme parks.
The apartment features a fully equipped kitchen, a spacious bathroom with a rain shower, and a private porch, making it ideal for couples seeking a comfortable and convenient base for exploring Orlando.
Modern 1br Suite W/ Full Kitchen & Balcony Near Epic Universe & Icon Park - Winter Park, FL
No reviews

Modern 1br Suite W/ Full Kitchen & Balcony Near Epic Universe & Icon Park

apartment, Orlando
This Orlando flat is centrally located, offering convenient access to major theme parks with Universal Studios and Islands of Adventure within 3.2 kilometres, ICON Park at 1.9 kilometres, and Epic Universe at 7.2 kilometres.
This 67 square metre luxury suite accommodates up to four guests, featuring a separate bedroom, living area, full kitchen with stainless steel appliances, private balcony, and in-suite washer/dryer, alongside access to hotel amenities including a fitness centre and Wi-Fi within a gated community.
New5 Apt Nrucf Petsok Private Patioentry Laundry - Winter Park, FL
8.0 3 reviews

New5 Apt Nrucf Petsok Private Patioentry Laundry

apartment, Union Park
This Union Park apartment, situated 4 kilometres from Boardwalk Bowl and 9.6 kilometres from the University of Central Florida, offers convenient access to local attractions and research facilities.
The 67-square-metre flat comprises one bedroom, one bathroom, and accommodates four guests, boasting amenities including a swimming pool, terrace, garden, parking, and a fully equipped kitchen with appliances such as a fridge, microwave, oven and stovetop; plus on-site water park access.
New Construction Home, 3 Blocks S Downtown Orlando, In Lake Davis Neighborhood - Winter Park, FL
10 4 reviews

New Construction Home, 3 Blocks S Downtown Orlando, In Lake Davis Neighborhood

apartment, Orlando
This 2-bedroom flat in Orlando's Lake Davis district is situated three blocks south of the city centre, offering proximity to Lake Eola (0.8 km), Orlando Health Hospital (1.3 km), Dr. Phillips Centre (1.1 km), and the Kia Centre (1.8 km), with Disney and Universal Studios within 25 km.
This accommodation for four guests features a full kitchen with high-end appliances including a convection oven and induction stovetop, a master bedroom with a king-size bed, a soaking tub in the bathroom, and a 2.4 x 4.8 metre balcony, alongside amenities such as a 75-inch QLED television and in-room Alexa music.

Popular Dog-Friendly Holiday Rentals in Winter Park, FL

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

Beautiful East Orlando Home Near Everything - Winter Park, FL
No reviews

Beautiful East Orlando Home Near Everything

apartment, Orlando
This holiday flat is situated in Orlando's Azalea Park district, a mere 3-4 minute drive from Ventura Country Club and East Orlando Shopping Centre.
This one-bedroom, one-bathroom flat accommodates two guests and offers amenities such as air conditioning, a garden, a fire pit, Wi-Fi, and a full kitchen, with convenient access to Universal Orlando Resort, Florida Mall, and Orlando International Premium Outlets.
Amazing Place In Exclusive Area Downtown Orlando - Winter Park, FL
9.9 91 reviews

Amazing Place In Exclusive Area Downtown Orlando

house, Orlando
This fully furnished house is situated in College Park, a quiet neighbourhood just 3 kilometres from Orlando city centre and 5 kilometres from Winter Park, with easy access to the Interstate 4 motorway. The property offers a private entrance, street parking, and can accommodate up to 3 guests, with a fully equipped kitchen, air conditioning, and internet access.
Tranquil Oasis: 4br Pool Home - Winter Park, FL
9.4 56 reviews

Tranquil Oasis: 4br Pool Home

apartment, Goldenrod
This Winter Park house, situated in a quiet neighbourhood a short drive (approximately 16km) from Park Avenue, Rollins College, and the University of Central Florida, offers convenient access to local attractions.
The four-bedroom, two-bathroom property sleeps eight guests and boasts a private fenced backyard with a swimming pool and hot tub, a fully equipped kitchen, and two parking spaces; nearby amenities include the Winter Park Farmers' Market and restaurants such as The Ravenous Pig and Prato.
New5 Apt Nrucf Petsok Private Patioentry Laundry - Winter Park, FL
9.4 15 reviews

New5 Apt Nrucf Petsok Private Patioentry Laundry

apartment, Union Park
This Union Park apartment is conveniently located approximately 8 kilometres from Addition Financial Arena and 8.7 kilometres from Spectrum Stadium, offering easy access to the University of Central Florida.
This one-bedroom, one-bathroom flat boasts 67 square metres of space, sleeping up to 7 guests and including a private patio, in-unit laundry, free Wi-Fi, and parking.
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