Compare Vacation Rentals & Airbnb in Winter Park, FL

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Winter Park, FL vacation rentals
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405 Rentals and Airbnb in Winter Park, FL

Best family friendly Winter Park, FL vacation rentals

Among the 405 accommodations in Winter Park, FL, here are the 4 best family friendly rentals

House Close To Downtown Orlando Has Walking Trail And Next To Baldwin Park Lake - Winter Park, FL
9.4 29 reviews

House Close To Downtown Orlando Has Walking Trail And Next To Baldwin Park Lake

apartment, Orlando
This three-bedroom, two-and-a-half-bathroom townhouse is situated in Baldwin Park, Orlando, a short 19-24 km drive from Downtown Orlando and within a 48 km radius of Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando.
The fully remodelled property sleeps six guests and offers a kitchen with fridge, microwave, and dishwasher, plus air conditioning, parking, and Wi-Fi; nearby amenities include Baldwin Lake, with its walking and cycling trails.
Airport & Downtown Orlando 15 Min| Disney 30 Min - Winter Park, FL
10 20 reviews

Airport & Downtown Orlando 15 Min| Disney 30 Min

apartment, Orlando
This centrally located flat in Orlando provides unparalleled convenience, situated a short 6-kilometre drive from Walt Disney World Resort and Universal Orlando Resort, with easy access to the I-4 for onward travel and a mere 20-kilometre journey to Orlando International Airport (MCO).
This family-friendly apartment accommodates up to 8 guests, offering 2 bathrooms, air conditioning, and a kitchen equipped with a fridge, microwave oven, and dishwasher, alongside the convenience of included internet and pet-friendly policies, all within a walkable distance to local shops and restaurants.
Pet Friendly 3 Bedroom Pool Home In The Heart Of Orlando - Winter Park, FL
9.0 16 reviews

Pet Friendly 3 Bedroom Pool Home In The Heart Of Orlando

apartment, Azalea Park
This Orlando flat in Azalea Park is situated with easy access to major motorways, shopping, and dining, placing Universal Studios (40 kilometres) and Walt Disney World (56 kilometres) within convenient reach.
This three-bedroom property offers accommodation for up to seven guests, featuring a private swimming pool, expansive outdoor space with artificial turf, air conditioning, and is equipped with a fridge, microwave, and dishwasher, making it ideal for families and pet owners.
The Canopy On Periwinkle- A Home Away From Home - Winter Park, FL
10 2 reviews

The Canopy On Periwinkle- A Home Away From Home

house, Goldenrod
This Orlando residence is situated approximately 12.3 kilometres from Addition Financial Arena and 13 kilometres from Spectrum Stadium, offering convenient access to downtown attractions such as the Kia Centre, 13.7 kilometres away, and Church Street Station, 14.9 kilometres distant.
This spacious 128 square metre house accommodates up to nine guests with four bedrooms, featuring a saltwater swimming pool, a garden, air conditioning, free WiFi, and private parking, with Orlando International Airport just 19.3 kilometres away.

Best Winter Park, FL vacation rentals with parking

Private City Oasis - Winter Park, FL
9.5 92 reviews

Private City Oasis

apartment, Azalea Park
This apartment is located in Azalea Park, just under 19 kilometres from downtown Orlando and its bars and restaurants, and within 48 kilometres of major theme parks like Universal Studios, Sea World, ICON Park, and Walt Disney World. It has received excellent ratings for location, cleanliness, and overall user experience.
This spacious home offers two bathrooms and can accommodate up to five guests. Amenities include a fully equipped kitchen, a private hot tub, a garden, and parking.
Comfortable 1 Bedroom Home - Winter Park, FL
9.4 36 reviews

Comfortable 1 Bedroom Home

apartment, Azalea Park
This Azalea Park apartment, conveniently located approximately 34km from Walt Disney World and 22km from Universal Studios Florida, offers easy access to Orlando's major theme parks.
The self-contained flat features a queen-size bed, a small kitchenette with fridge, freezer and microwave, a shared backyard with firepit, free parking for two cars, and accommodates two guests.
Balfour Villa - Winter Park, FL
9.4 137 reviews

Balfour Villa

house, Winter Park
This two-bedroom house is located in Winter Park, just a short walk from Park Avenue, a bustling street lined with shops and restaurants, and within 5 kilometres of Rollins College.
The property boasts a private swimming pool, a well-equipped kitchen, and a spacious living area, ideal for a family or group of friends seeking a relaxing and comfortable stay in the heart of Winter Park.
Downtown (Ivanhoe Village) Loft Apartment - Winter Park, FL
9.8 1358 reviews

Downtown (Ivanhoe Village) Loft Apartment

apartment, Orlando
This Orlando studio apartment is situated in Ivanhoe Village, a short distance from Lake Ivanhoe, the Orlando Science Center, and the Orlando Museum of Art.
The self-contained apartment, sleeping two guests, features a kitchenette with fridge and microwave, keyless entry, and is close to numerous breweries and bars.

Frequently Asked Questions about vacation rentals in Winter Park, FL

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

    Winter Park is a charming city! For a first-timer, you definitely shouldn't miss the scenic beauty of the Central Park, a beautiful green space in the heart of Winter Park, and the iconic Rollins College, a historic college campus with beautiful architecture. Also, take a stroll down Park Avenue, a vibrant street with shops, restaurants, and art galleries.
  • What are the best Airbnb and vacation rentals in Winter Park, FL?

    Upscale Loft Space Close To Downtown, Downtown Lake Eola Historic House 1 Or 2 Bed and Moniker Manor (Entire Home Near Downtown) are the most popular Airbnb and vacation rentals in Winter Park, FL among travelers.

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

    The best neighbourhood for a vacation rental really depends on your preferences. If you want to be close to the action, consider staying in the Winter Park Village, close to shops and restaurants. For a more residential feel, Baldwin Park is a great choice, known for its beautiful homes and parks. If you want a quieter experience, Lake Howell is a good option, with its peaceful lakeside setting.
  • What are the most popular Airbnbs in Winter Park, FL?

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

    Winter Park is a great place for families! The Charles Hosmer Morse Museum of American Art is a great place to explore with kids, featuring a collection of Tiffany glass. For a fun day out, the Winter Park Scenic Boat Tour is a great way to see the city from the water. And don't forget the Central Park, with its playgrounds and open spaces, perfect for a picnic.
  • What are the best vacation 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 really depends on your preferences. Peak season is from December to April, when the weather is mild and sunny, so expect higher prices. If you're looking for a better deal, consider visiting during the shoulder seasons, May to June or September to November, when the weather is still pleasant but the crowds are smaller.
  • 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 lively events calendar. The Winter Park Sidewalk Art Festival is a must-see for art lovers, held in March. The Winter Park Autumn Art Festival, held in October, is another great option for art enthusiasts. For a festive experience, the Winter Park Christmas in the Park is a magical event held in December.
  • 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 plenty of budget-friendly activities. A stroll through the Central Park is a great way to enjoy the outdoors without spending a penny. For a unique experience, visit the Albin Polasek Museum & Sculpture Gardens, a beautiful museum and garden with free admission on the first Saturday of every month. The Winter Park Farmers Market is a great place to find local produce and crafts at affordable prices.
  • What are the best restaurants with local dishes in Winter Park, FL?

    For a taste of local cuisine, The Wine Room is a great spot, known for its Florida-inspired dishes. Bosphorous is another popular choice, serving authentic Turkish cuisine. If you're looking for a more casual dining experience, The Porch is a great option, with a menu featuring fresh, seasonal dishes.
  • What are the best walking or cycling routes in Winter Park, FL?

    Winter Park is a very walkable city. For a scenic walk, try the Winter Park Trail, a paved trail that runs along the shores of Lake Maitland. For a longer ride, the Cady Way Trail is a great option, a 12 km paved trail that stretches through the city.
  • Are there pet-friendly attractions in Winter Park, FL?

    Winter Park is a very dog-friendly city. The Central Park is a great place to let your furry friend run around. The Winter Park Scenic Boat Tour also welcomes well-behaved dogs on board. Many restaurants and shops in Winter Park are also pet-friendly.
  • What are the benefits of choosing a vacation rental in Winter Park, FL?

    Vacation rentals in Winter Park offer a more spacious and comfortable option compared to hotels. They often include amenities like a kitchen and laundry facilities, which can be very convenient for families or groups. Vacation rentals also offer more privacy and flexibility, allowing you to come and go as you please.
  • What are the top sports attractions and facilities in Winter Park, FL?

    Winter Park has a variety of sports attractions and facilities. The Winter Park Racquet Club is a popular spot for tennis enthusiasts. The Winter Park Golf Course is a beautiful 18-hole course. For a more casual experience, there are also several parks with basketball courts, volleyball courts, and playgrounds.

Popular destinations

Best Winter Park, FL vacation rentals with a balcony

Mills Cottage - Winter Park, FL
9.7 4 reviews

Mills Cottage

house, Orlando
Mills Cottage, a centrally located Orlando dwelling, is less than 0.6km from the city centre, offering easy access to the Amway Center (3km) and Camping World Stadium (5.3km).
This one-bedroom, one-bathroom property sleeps seven guests and boasts a private pool, Jacuzzi, sauna, free Wi-Fi, and free private parking, alongside a fully equipped kitchen and garden.
Incredible Private Lakefront Cottage Retreat - Winter Park, FL
10 38 reviews

Incredible Private Lakefront Cottage Retreat

cottage, Altamonte Springs
This charming cottage is situated in Altamonte Springs, Florida, just a short distance from the Altamonte Mall and Advent Florida Hospital North, and within easy reach of Interstate-4, Orlando International Airport, and major theme parks. The cottage has received excellent user ratings, making it a popular choice for travellers.
The cottage offers one bedroom and one bathroom, spanning 102 square metres and comfortably accommodating up to four guests. Enjoy a range of features including a private boat ramp, pedal boat, outdoor fire pit, hammock, and outdoor shower, perfect for relaxing and enjoying the outdoors.
Peaceful Poolside Retreat Near Orlando Health.  Resort Style Amenities Workspace - Winter Park, FL
No reviews

Peaceful Poolside Retreat Near Orlando Health. Resort Style Amenities Workspace

apartment, Orlando
This two-bedroom flat is situated in Orlando's Wadeview Park district, offering a residential setting approximately 3 kilometres from downtown Orlando and within easy reach of Orlando Health and the Mall at Millenia.
This fully furnished second-floor condo sleeps up to four guests, featuring a dedicated workspace, resort-style swimming pool, and in-unit laundry, with included utilities and WiFi, plus one covered parking space.
Spacious 4 Bd/2bath 2100 Sq Ft Downtown Condo - Winter Park, FL
9.0 8 reviews

Spacious 4 Bd/2bath 2100 Sq Ft Downtown Condo

apartment, Orlando
This Lake Eola Heights apartment offers a convenient stay, less than 2.4 kilometres from Lake Eola Park and the Dr. Phillips Center for the Performing Arts, and within 4.8 kilometres of Camping World Stadium and the Amway Center.
This four-bedroom, two-bathroom dwelling sleeps eight guests and includes a fully equipped kitchen, balcony, on-site fitness centre, parking, and is a smoke-free property.

Best pet friendly Winter Park, FL vacation rentals

Among the 405 accommodations in Winter Park, FL, here are the 4 best pet friendly rentals

️Walk To Lake Eola & Restaurants - Winter Park, FL
9.0 49 reviews

️Walk To Lake Eola & Restaurants

apartment, Orlando
This Thornton Park flat is less than 1.6km from Lake Eola and the Dr. Phillips Center for the Performing Arts, and within 4.8km of Camping World Stadium.
This two-bedroom, one-bathroom apartment sleeps four, includes in-unit laundry, and offers excellent access to Thornton Park's restaurants and shops.
Enjoyable And Cozy 1-bedroom Apartment With Ac In Winter Park - Winter Park, FL
No reviews

Enjoyable And Cozy 1-bedroom Apartment With Ac In Winter Park

apartment, Winter Park
This Winter Park flat offers a prime location directly opposite Full Sail University, a mere 15-kilometre drive from Orlando International Airport (MCO) and in close proximity to the University of Central Florida (UCF).
This one-bedroom, one-bathroom flat accommodates up to two guests and features air conditioning, Wi-Fi, and access to an on-site swimming pool, with shopping at Orlando International Premium Outlets and Mall at Millenia, plus attractions like Tinker Field and Wekiwa Springs State Park, all within easy reach.
Massive Corner 3 Bedroom 2 Bath - Winter Park, FL
10 5 reviews

Massive Corner 3 Bedroom 2 Bath

apartment, Orlando
This recently renovated three-bedroom, two-bathroom flat offers prime central Orlando accommodation, situated within 500 meters of dining, coffee shops, and the Amway Center, with secure, covered parking and 24-hour doorman and fob access. Guests can enjoy exclusive use of the 9th-floor amenities, including a TV area and outdoor grill, alongside full access to a 24-hour gym, all within a building featuring beautiful park views and accommodating up to six people.
2 Bdrm Penthouse With Billiards - Winter Park, FL
9.8 11 reviews

2 Bdrm Penthouse With Billiards

apartment, Orlando
This Orlando penthouse apartment is situated in the city centre, less than 0.6km from various attractions and 14km from Orlando International Airport.
The 150 square metre dwelling boasts two bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, a billiards table, free Wi-Fi, and accommodates up to seven guests.
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