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

Great Central Location - Winter Park, FL
8.0 1 review

Great Central Location

house, Orlando
This holiday let is located 2.6 kilometres from central Orlando, 5.5 kilometres from the Kia Centre and 7.4 kilometres from Camping World Stadium.
This 60 square metre holiday home offers accommodation for up to 7 guests with air conditioning, Wi-Fi, a fully equipped kitchen, and a private terrace, with pets welcome.
Florida Poolside Paradise A Great Place To Unwind! - Winter Park, FL
10 126 reviews

Florida Poolside Paradise A Great Place To Unwind!

apartment, Maitland
This four-bedroom holiday home in Maitland, Florida, is conveniently located just a short drive from Orlando International Airport, Disney World, Universal Studios, and International Drive. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The self-catering property can accommodate up to eight guests and features a private pool and screened-in patio, a gourmet kitchen, and a spacious and comfortable living area. Guests can also enjoy a range of amenities including air conditioning, a swimming pool, a garden, parking, and internet access.
Cozy 2bd 2bth House Walk To Local Gems - Winter Park, FL
9.0 8 reviews

Cozy 2bd 2bth House Walk To Local Gems

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.
Apartment ∙ 2 Bedrooms ∙ 4 Guests - Winter Park, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Orlando
This Orlando flat is located within a secure resort community, 16 kilometres from the main theme parks and 8 kilometres from Orlando International Airport.
This two-bedroom, two-bathroom apartment sleeps four and offers resort-style amenities including a swimming pool, fitness centre, tennis, pickleball, and basketball courts, alongside a furnished patio and a fully equipped kitchen.

Best Winter Park, FL vacation rentals with parking

The Hideaway At College Park - Winter Park, FL
9.5 26 reviews

The Hideaway At College Park

apartment, Orlando
This Orlando flat is located in the walkable College Park district, offering direct access to Lake Ivanhoe for paddle boarding with views of the downtown skyline and proximity to local restaurants and museums.
This renovated 1920s cottage provides accommodation for up to three guests with two bedrooms, one bathroom, a private fenced garden with a pond and deck, a fully equipped kitchen, air conditioning, Wi-Fi, and on-site parking for three cars.
Peaceful Orlando Pool Home On Quiet Street - Winter Park, FL
9.7 6 reviews

Peaceful Orlando Pool Home On Quiet Street

apartment, Orlando
This Orlando flat is located in a quiet residential district, offering straightforward access to local shops, eateries, and main roads, placing you a short drive from Central Florida's attractions.
This property, suitable for up to five guests, features a private swimming pool, a tropical garden, a Spanish-style kitchen equipped with a fridge, freezer, microwave, and dishwasher, air conditioning, and a Florida room for relaxation.
The Clementine Boho Home In Orlandos Food Scene - Winter Park, FL
9.6 26 reviews

The Clementine Boho Home In Orlandos Food Scene

apartment, Orlando
This Orlando guest house, situated in the Park Lake – Highland neighbourhood, offers easy access to Winter Park and is within a 32- to 56-kilometre radius of major theme parks such as Universal Orlando Resort, SeaWorld Orlando, and Walt Disney World Resort.
The self-contained unit sleeps five, features a kitchen with a fridge and microwave, a private backyard, and access to a tennis court, parking, and outdoor amenities including a barbecue and trampoline; nearby attractions include the Central Florida Fairgrounds and Camping World Stadium.
Apartment| Downtown Orlando 10 Min & Disney 25 Min - Winter Park, FL
9.3 25 reviews

Apartment| Downtown Orlando 10 Min & Disney 25 Min

apartment, Fairview Shores
This 1-bedroom flat in Winter Park provides easy access to Orlando's main attractions, situated 5 kilometres from Downtown Winter Park and within a 40-kilometre drive of Disney World.
This second-floor apartment welcomes up to three guests and offers amenities including internet, a kitchen, and air conditioning, with parking available and pets permitted.

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

Modern Getaway  Close To Disney - Winter Park, FL
10 1 review

Modern Getaway Close To Disney

apartment, Orlando
This Orlando flat offers easy access to Walt Disney World and Universal Orlando Resort, being just a short drive away, and is also conveniently located approximately 3 kilometres from The Mall at Millenia and Florida Mall.
This residence accommodates up to eight guests and features a fully equipped kitchen, in-home laundry, air conditioning, Wi-Fi, a private backyard, and parking, providing a comfortable base for exploring local attractions like the Kia Centre and Camping World Stadium.
Romantic Lakefront Getaway With Balcony Near Downtown Orlando - Winter Park, FL
No reviews

Romantic Lakefront Getaway With Balcony Near Downtown Orlando

cottage, Conway
This non-smoking cottage, situated by the water in Orlando, is a 13-minute drive from the Kia Centre and a 8-minute drive from Florida Mall.
This one-bedroom, one-bathroom lodge accommodates two guests and features a garden, balcony, Wi-Fi, air conditioning, and a full kitchen, with lake activities and on-site parking readily available.
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.
Spring Lake King Balcony Suite - Winter Park, FL
8.4 16 reviews

Spring Lake King Balcony Suite

apartment, Conway
This pet-friendly Conway apartment, near Spring Lake, is situated approximately 3.5 kilometres from Conway's city centre and within 7-8 kilometres of the Amway Center, Camping World Stadium, and Orlando International Airport.
The 33-square-metre self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a private balcony, garden, parking, Wi-Fi, and a kitchen with a dishwasher, microwave, and fridge.

Best pet friendly Winter Park, FL vacation rentals

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

3br House Minutes Walk To Park Ave And Golf Course - Winter Park, FL
9.8 33 reviews

3br House Minutes Walk To Park Ave And Golf Course

house, Winter Park
This three-bedroom Winter Park apartment, sleeping six, is situated 0.32 kilometres from Park Avenue and within walking distance of the SunRail station, offering easy access to shops, restaurants, and public transport links.
The self-contained property features a studio with en-suite bathroom, three queen-sized beds, three-car parking, air conditioning, and Wi-Fi, all within a 24-hour secure, non-smoking environment.
Firepit Grill & 3 Kings W/ Tvs - Winter Park, FL
9.5 66 reviews

Firepit Grill & 3 Kings W/ Tvs

apartment, Azalea Park
This Azalea Park flat is located in a residential area, offering convenient access to local amenities and approximately a 15-minute drive from the main Azalea Park attractions.
This three-bedroom, two-bathroom apartment accommodates up to six guests and features a fully fenced garden with a grill, patio seating, and a firepit, alongside air conditioning, Wi-Fi, and two dedicated parking spaces.
Cozy 3br Near Mills | Walk To Food, Coffee & Shops - Winter Park, FL
8.9 9 reviews

Cozy 3br Near Mills | Walk To Food, Coffee & Shops

apartment, Orlando
This flat in Orlando is located in the Mills 50 and Little Vietnam district, offering a 500-metre walk to Michelin-starred restaurants, bars, and a Publix supermarket, with easy access to the Central Business District.
This stylish 3-bedroom, 2.5-bathroom property sleeps up to 8 guests, featuring air conditioning, a kitchen with a fridge, freezer, microwave, and dishwasher, and a private garden.
Newly Constructed Modern Pet Friendly Zen Home With Private Home Theater & Hot Tub! Home - Winter Park, FL
9.6 6 reviews

Newly Constructed Modern Pet Friendly Zen Home With Private Home Theater & Hot Tub! Home

house, Orlando
This studio apartment is conveniently located in central Orlando, just 4.5 kilometres from Church Street Station and Amway Center, placing you within easy reach of the city's main attractions. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The self-catering studio offers a modern and comfortable layout, perfect for a relaxing stay. Guests can enjoy a range of amenities including a private hot tub, outdoor fireplace, garden, free parking, a fully equipped kitchen, and a washing machine.
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