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.

New5 Apt Nrucf Petsok Private Patioentry Laundry - Winter Park, FL
No reviews

New5 Apt Nrucf Petsok Private Patioentry Laundry

apartment, Union Park
Holiday rental. This accommodation is located in Union Park.
Services and facilities: air conditioning, a washing machine and a fridge. This apartment is very convenient for families.
Walk To Park Avenue & Beautiful Lake Virginia! - Winter Park, FL
10 3 reviews

Walk To Park Avenue & Beautiful Lake Virginia!

apartment, Winter Park
This three-bedroom house is situated in a well-established Winter Park neighbourhood, within a short walking distance of Park Avenue's shops and restaurants, Rollins College, and Lake Virginia.
This family-friendly property offers three bedrooms, two and a half bathrooms, a fully equipped kitchen including a dishwasher, a swimming pool, and a garden, sleeping up to six guests and is close to local amenities.
Recharge @ Timberland Lodge: Pool  Hottub Sauna - Winter Park, FL
No reviews

Recharge @ Timberland Lodge: Pool Hottub Sauna

apartment, Wekiwa Springs
This charming chalet is located in Longwood, Florida, just a short drive from Wekiwa Springs State Park and other local attractions. It’s rated excellent by previous guests and offers a peaceful retreat in a tranquil setting.
The chalet has four bedrooms and three bathrooms, comfortably accommodating up to eleven guests. It also features a private pool, sauna, and outdoor shower, alongside a fully equipped kitchen, air conditioning, and a jacuzzi for ultimate relaxation.
Quiet Retreat 15 Minutes From Downtown Orlando, Orlando Airport International! - Winter Park, FL
9.6 25 reviews

Quiet Retreat 15 Minutes From Downtown Orlando, Orlando Airport International!

apartment, Azalea Park
Golden Cove Rental is situated in Azalea Park, a peaceful residential neighbourhood in Orlando, just 15km from Orlando International Airport, Interstate 4, and the city centre. This apartment has received very good user ratings, making it a popular choice for travellers.
This three-bedroom, two-bathroom property can accommodate up to 10 guests, making it ideal for families or groups. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a tennis court, and parking.

Best Winter Park, FL holiday rentals with parking

Sleek, Spacious & Central  Your Ideal Getaway - Winter Park, FL
8.8 3 reviews

Sleek, Spacious & Central Your Ideal Getaway

apartment, Fairview Shores
This private downstairs unit in Fairview Shores, Winter Park, FL, is located within 5 kilometres of Winter Park Downtown and Orlando Downtown, and is also close to Rollins College and Full Sail University.
This pet-friendly one-bedroom flat offers accommodation for two guests, with a kitchen featuring a fridge and microwave, air conditioning, and free Wi-Fi, plus one allocated parking space and opportunities for nearby motor boating and fishing.
Spacious Private & Lovely - Winter Park, FL
No reviews

Spacious Private & Lovely

apartment, Winter Park
This one-bedroom flat is located adjacent to Interlachen Country Club in Winter Park, offering a 5-minute walk to Lake Howell Plaza and a 5-minute drive to Park Avenue's shops and restaurants.
This accommodation for four guests provides internet, air conditioning, a kitchen, and parking, with Universal Orlando Resort 25-35 kilometres and Walt Disney World 35-45 kilometres away.
Oasis Under The Oak Tree. - Winter Park, FL
No reviews

Oasis Under The Oak Tree.

apartment, Goldenrod
This Goldenrod flat, located in Winter Park, is a rural retreat situated 8 kilometres from the University of Central Florida and 2.9 kilometres from Full Sail University, with theme parks 47 kilometres away and Orlando's downtown 40 kilometres distant.
This 39 square metre flat offers accommodation for up to four guests, featuring a kitchen with a fridge and microwave, air conditioning, a garden, spa, and parking, with opportunities for water sports and nearby attractions including the Mall at Millenia and Wekiwa Springs State Park.
Cozy Private Apartment In Casselberry - Winter Park, FL
10 3 reviews

Cozy Private Apartment In Casselberry

apartment, Casselberry
This Casselberry flat is situated in a quiet district, offering convenient access to Orlando's attractions, located 48 kilometres from Walt Disney World Resort and Orlando International Airport, 32 kilometres from Downtown Orlando, and 16 kilometres from Winter Park.
This two-bedroom flat, accommodating up to four guests, features a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, complimentary WiFi, and free on-site parking, with a private balcony for outdoor relaxation.

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.

The Tiny Cottage In The Springs/ Central Fl - Winter Park, FL
10 1 review

The Tiny Cottage In The Springs/ Central Fl

chalet, Altamonte Springs
Chalet rental with an excellent rating of 100% based on 1 reviews. You will stay in Altamonte Springs.
Facilities and services: a fridge, an iron and air conditioning. This accommodation is very convenient for families.
Orlando Golf Gated Community, Pools, Hot Tub, Tennis, Golf, Fitness, Playground - Winter Park, FL
9.8 49 reviews

Orlando Golf Gated Community, Pools, Hot Tub, Tennis, Golf, Fitness, Playground

apartment, Orlando
This smoke-free apartment is conveniently located in Ventura, just a short distance from Ventura Country Club and within a 10-minute drive from Lake Conway and Hoffner Plaza Shopping Center. The apartment has consistently received excellent ratings from previous guests.
The property features two bedrooms and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, a swimming pool, a Jacuzzi, a fitness centre, a terrace, and free parking.
Enclave Studio  1 Mi To Universal W/ Pool - Winter Park, FL
No reviews

Enclave Studio 1 Mi To Universal W/ Pool

studio, Orlando
This newly-remodeled studio apartment in Orlando's Florida Center neighbourhood is situated just over 1.6 kilometres from Universal Studios Florida and Universal's Islands of Adventure, and is located directly on International Drive for immediate access to dining and entertainment.
This accommodation for four guests features a kitchenette equipped with a fridge and microwave, air conditioning, a private balcony with resort and skyline views, and offers access to resort amenities including two outdoor pools, a heated indoor pool, a jacuzzi, fitness centre, tennis court, children's pool, and playground, with complimentary parking and Wi-Fi provided.
Lake Eola Thornton Park Studio With Balcony - Winter Park, FL
9.0 9 reviews

Lake Eola Thornton Park Studio With Balcony

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.

Popular Dog-Friendly Holiday Rentals in Winter Park, FL

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

Cute And Cozy Studio W/ Jacuzzi! - Winter Park, FL
8.8 8 reviews

Cute And Cozy Studio W/ Jacuzzi!

studio, Orlando
This Orlando studio apartment, located in the Azalea Park neighbourhood, is 22.4 km from Universal Studios Florida, 34 km from Walt Disney World Resort, and offers convenient access to Orlando International Airport.
The 33-square-metre self-catering unit sleeps two, features a queen-size bed, a private patio with a jacuzzi and fire pit, free parking for two cars, and includes a kitchenette with a fridge and microwave; a laundry room is available on request after 4 pm.
Floyd - Luxury 2br W/ Rooftop Pool, Gym, Balcony - Winter Park, FL
10 1 review

Floyd - Luxury 2br W/ Rooftop Pool, Gym, Balcony

apartment, Orlando
This modern luxury condominium in Orlando offers excellent city views and is centrally located, placing you within a 1.6 to 2.4 kilometre drive of the Amway Centre, Downtown Orlando, International Drive, and the Orlando Convention Centre, with Disneyworld and Universal Studios also within easy reach. This two-bedroom, two-bathroom flat accommodates up to five guests and features a fully equipped kitchen, high-speed Wi-Fi, air conditioning, and access to building amenities such as a rooftop swimming pool and fitness centre, with pets permitted.
Luxury And Location!!! - Winter Park, FL
10 4 reviews

Luxury And Location!!!

apartment, Winter Park
This Winter Park apartment is situated just 0.5 km from Park Avenue and 0.3 km from Winter Park Village, offering easy access to Winter Park's key attractions.
The 116-square-metre property boasts two bedrooms, two bathrooms, sleeps five guests, and includes a swimming pool, spa, and on-site parking, plus high-speed internet access.
Cozy Apt With Pool, Hot Tub, Golf, Near Downtown - Winter Park, FL
No reviews

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

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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