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

Lake Marion Apt W/ Canoe In Altamonte Springs! - Winter Park, FL
9.8 190 reviews

Lake Marion Apt W/ Canoe In Altamonte Springs!

apartment, Altamonte Springs
This charming one-bedroom house is situated in Altamonte Springs, just 18 kilometres from downtown Orlando and Church Street Station, offering a peaceful escape from the city's hustle and bustle. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
The 42 square metre house comfortably accommodates two guests and features a separate bedroom and living area. Guests can enjoy a fully equipped kitchen, a private garden, a spa, free Wi-Fi, air conditioning, and direct access to Lake Marion, complete with a canoe for exploring the tranquil waters.
Private Luxury Pool / Swim Up Bar / Smart-home - Winter Park, FL
9.7 330 reviews

Private Luxury Pool / Swim Up Bar / Smart-home

apartment, Orlando
This Orlando villa is situated in College Park, just a few kilometres from downtown, Winter Park, and Universal Studios, offering easy access to the city's attractions. It has received excellent ratings for its location, cleanliness, and overall experience.
The three-bedroom villa, spanning 139 square metres, comfortably accommodates up to eight guests. It features a resort-style pool, a hot tub, a custom-built sunken bar, a fully equipped kitchen, and a range of other amenities, including bicycles and a coffee bar.
Casa Bella - Winter Park, FL
9.8 166 reviews

Casa Bella

apartment, Maitland
This family-friendly house is located in Maitland, just 5km from Lake Lily Park, Altamonte Mall, and The Center of Winter Park Shopping Center, offering easy access to a variety of attractions and amenities. The property boasts excellent user ratings, reflecting its popularity among travellers.
The house spans 260 square metres and comfortably accommodates up to 8 guests. It features a private pool, a garden, a barbecue grill, and a fully equipped kitchen, providing everything you need for a relaxing and enjoyable stay.
The Tiny Cottage In The Springs/ Central Fl - Winter Park, FL
8.6 41 reviews

The Tiny Cottage In The Springs/ Central Fl

chalet, Altamonte Springs
The Tiny Cottage in the Springs/ Central FL is located in Orlando, just 19 kilometres from Church Street Station and 19 kilometres from Amway Center, offering easy access to the city's attractions. This charming cottage has excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The cottage, covering 46 square metres, has two bedrooms and one bathroom, comfortably accommodating up to five guests. It offers a fully equipped kitchen, a dining area, a flat-screen TV, a terrace, a garden, free parking and Wi-Fi, plus a welcome package with wine or champagne, chocolates or cookies, and a delicious American breakfast.

Best Winter Park, FL vacation rentals with parking

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.
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.
Roy's Guest House - Winter Park, FL
10 102 reviews

Roy's Guest House

house, Orlando
Roy's guest house offers a private, quiet retreat in Orlando, Florida, conveniently located 5km from Church Street Station, 6km from the Amway Center, and 7.6km from Camping World Stadium.
This self-catering property boasts a 39 square metre floor area with one bedroom, one bathroom, sleeping up to three guests, and features a fully equipped kitchen, free Wi-Fi, and a private garden.
The Pineapple Express - Winter Park, FL
8.8 4 reviews

The Pineapple Express

apartment, Orlando
This Orlando flat is located approximately 5 kilometres from the Kia Centre and Church Street Station, and 6.9 kilometres from Camping World Stadium.
This 111 square metre flat offers accommodation for up to 9 guests, featuring a fully equipped kitchen, complimentary WiFi, and on-site parking, with a check-out time of 10:00 AM.

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

Lake House - Winter Park, FL
9.8 207 reviews

Lake House

apartment, Orlando
This family-friendly house is located near Lake Eola in Orlando, within 1.6 kilometres of Orlando Regional Medical Center and Lake Eola Park, offering easy access to various attractions. The property has consistently received excellent ratings for user experience, location, and cleanliness.
The house has two bedrooms, accommodating up to four guests, and provides a range of amenities for a comfortable stay. Guests can enjoy the swimming pool, jacuzzi, sauna, spa, fitness centre, tennis court, and garden, as well as a fully equipped kitchen and free Wi-Fi.
Love Nest Studio Nearby Highways And Airport - Winter Park, FL
No reviews

Love Nest Studio Nearby Highways And Airport

studio, Azalea Park
This Azalea Park studio apartment is situated in Orlando, offering excellent access to main routes such as the 408, 417, and I-4, with Orlando International Airport just 29 kilometres away and popular theme parks like Walt Disney World Resort 56 kilometres distant.
This private oasis, ideal for two guests, features air conditioning, complimentary Wi-Fi, and a kitchen equipped with a fridge and microwave, with a terrace for relaxation and proximity to Full Sail University, the University of Central Florida, and shopping centres like the Florida Mall.
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.
Lake House - Winter Park, FL
8.0 5 reviews

Lake House

house, Orlando
Lake House, situated in Orlando near the city centre, is a short drive (approx. 3km) from the Amway Center and Camping World Stadium, and within easy reach of Universal Studios Florida and the Florida Mall.
This one-bedroom, two-bathroom property sleeps seven guests and boasts a private pool, Jacuzzi, sauna, fully equipped kitchen with minibar, free Wi-Fi, private parking, and a relaxing garden – perfect for exploring Orlando's attractions.

Best pet friendly Winter Park, FL vacation rentals

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

2 Full Beds - Winter Park, FL
No reviews

2 Full Beds

apartment, Fairview Shores
This apartment in Fairview Shores offers convenient access, situated just off Interstate 4 and less than 48 kilometres from Universal Studios, with Central Orlando 8 kilometres away and Amway Arena under a 24-minute drive.
This 19 square metre flat, suitable for up to four guests, features air conditioning, an outdoor swimming pool, an on-site laundrette, and rooms equipped with cable TV and Wi-Fi, with pets being welcome.
Fern Park Retreat - Winter Park, FL
9.9 68 reviews

Fern Park Retreat

apartment, Maitland
This renovated 1958 guest house, situated in the Fern Park district of Maitland, Seminole County, is less than 1.6km from the SunRail station and offers easy access to major highways and Orlando attractions.
The self-contained property sleeps two guests in two bedrooms and one bathroom, boasting a modern kitchen with dishwasher, air conditioning, a private fenced garden, and parking; kayaks and a BBQ are available on request.
Winter Park 3br | Near Park Ave & Rollins | Pets - Winter Park, FL
9.8 43 reviews

Winter Park 3br | Near Park Ave & Rollins | Pets

apartment, Winter Park
This three-bedroom house in Winter Park, Florida, is conveniently located within a 3km radius of AdventHealth Winter Park, Rollins College, Park Avenue, and Winter Park Village.
The self-catering property sleeps six guests and boasts a fully equipped kitchen with dishwasher, a garden, fitness centre, and parking, plus excellent guest reviews for cleanliness and location.
Thornton Park Guest Suite - Lake Eola Private - Winter Park, FL
9.8 849 reviews

Thornton Park Guest Suite - Lake Eola Private

house, Orlando
This Orlando studio apartment is situated in Thornton Park, a short distance (approximately 2-3km) from Lake Eola and within easy reach of Walt Disney World Resort and the Orange County Convention Center.
The self-contained apartment features terracotta tiled floors, a private garden seating area, high-speed internet (300 mb/sec), accommodates two guests, and includes high-quality toiletries.
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