Compare Vacation Rentals & Airbnb in Winter Park, FL

288 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Winter Park, FL vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

288 Rentals and Airbnb in Winter Park, FL

Best family friendly Winter Park, FL vacation rentals

Among the 288 accommodations in Winter Park, FL, here are the 4 best family friendly rentals

King/queen Bungalow W/ Porch | Central Vibey Area - Winter Park, FL
10 267 reviews
Winter Park, FL
11/08 – 13/08
$285/nighttotal: $570 (2 )

King/queen Bungalow W/ Porch | Central Vibey Area

1 2
bungalow , Orlando
This charming bungalow is located in the ColonialTown North district of Orlando, just 10 minutes from Winter Park and within easy reach of Universal Studios, Disney, and the airport. The property has received excellent ratings for location, cleanliness, and user experience.
The two-bedroom, two-bathroom home comfortably sleeps five guests and features a private front porch, a well-equipped kitchen, and a relaxing living area. Guests can enjoy a host of amenities including free laundry facilities, fast internet, and smart TVs, making it ideal for a comfortable and enjoyable stay.
Modern, Charming Home In The Heart Of Winter Park- Perfect For A Couples Retreat Or Small Group! - Winter Park, FL
9.8 17 reviews
Winter Park, FL
03/09 – 08/09
$412/nighttotal: $2060 (5 )

Modern, Charming Home In The Heart Of Winter Park- Perfect For A Couples Retreat Or Small Group!

3 2
apartment , Winter Park
This Winter Park house, near Park Avenue, Rollins College, and Winter Park Village, offers easy access to AdventHealth Winter Park (under 2 km), Rollins College and Park Avenue (around 8 km), and Winter Park Village (approximately 12 km).
The 1100 square metre property boasts three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen with stainless steel appliances, a garden, parking, and Wi-Fi; nearby attractions include the Morse Museum and Dr. Phillips Center for the Performing Arts.
Sleek 2br Near Disney, Universal Stu & Downtown/ormc - Winter Park, FL
Winter Park, FL
03/07 – 31/07
$232/nighttotal: $6496 (28 )

Sleek 2br Near Disney, Universal Stu & Downtown/ormc

2 2
apartment , Orlando
This two-bedroom flat in Orlando's Lancaster Park district is conveniently situated a 5-minute drive from the Kia Centre and a 4-minute drive from the Dr. Phillips Centre for the Performing Arts, offering easy access to major attractions like Universal Orlando Resort.
This 800 square meter apartment, suitable for up to six guests, features air conditioning, Wi-Fi, a fully equipped kitchen with an oven and microwave, and on-site parking, ideal for families visiting Orlando's theme parks.
Large, Beautiful, Very Comfortable One Bedroom On Small Lake - Winter Park, FL
9.9 226 reviews
Winter Park, FL
03/07 – 31/07
$367/nighttotal: $10276 (28 )

Large, Beautiful, Very Comfortable One Bedroom On Small Lake

1 2
apartment , Orlando
This family-friendly holiday home is located just under 2 kilometres from Lake Eola Park and its surrounding area, offering a peaceful escape from the hustle and bustle of downtown Orlando. The property has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom property spans 46 square metres and can comfortably accommodate two guests. The house is equipped with a fully-equipped kitchen, a private pool, a spa, a sauna, a gym, and a tennis court, providing plenty of opportunities for relaxation and entertainment.

Best Winter Park, FL vacation rentals with parking

Entire 5 Bedroom Home In Winter Park Fl - Winter Park, FL
Winter Park, FL
20/06 – 27/06
$302/nighttotal: $2114 (7 )

Entire 5 Bedroom Home In Winter Park Fl

1 6
house , Casselberry
This four-bedroom detached house is situated in Winter Park, Florida, offering convenient access to Orlando attractions, located approximately 13.5 kilometres from the Kia Centre and Church Street Station.
This property provides accommodation for up to 21 guests with a fully equipped kitchen, two bathrooms, air conditioning, and complimentary Wi-Fi, with free private parking available.
London House | Orlando Airport Private Condo - Winter Park, FL
10 1 review
Winter Park, FL
17/06 – 23/06
$197/nighttotal: $1182 (6 )

London House | Orlando Airport Private Condo

1 1
apartment , Orlando
This one-bedroom flat, situated in Orlando's South Semoran district, offers excellent access, being 8 kilometres from Orlando International Airport and 24 kilometres from Universal Studios Florida.
This accommodation provides a fully equipped kitchen, complimentary toiletries, on-site laundry, high-speed WiFi, and free parking for two cars, comfortably accommodating up to three guests.
Close To The Action, Peaceful When You Return - Winter Park, FL
Winter Park, FL
02/08 – 04/08
$310/nighttotal: $620 (2 )

Close To The Action, Peaceful When You Return

2 6
house , Orlando
This holiday let is centrally located in Orlando, offering easy access to downtown attractions such as Church Street Station (1.8 km) and the Kia Centre (2.1 km), with Camping World Stadium 4.2 km away.
This accommodation provides 93 square metres of living space, accommodates up to 11 guests with 2 bedrooms and 1 bathroom, and features a fully equipped kitchen with a dishwasher, air conditioning, free WiFi, and a garden.
Downtown Orlando-harwood House-lake Eola-historic - Winter Park, FL
9.8 271 reviews
Winter Park, FL
11/08 – 13/08
$206/nighttotal: $412 (2 )

Downtown Orlando-harwood House-lake Eola-historic

1 2
apartment , Orlando
This completely renovated guesthouse is located in the quiet Eola Heights Historic District, just under a kilometer from Lake Eola and a short walk from the Orange County Courthouse and the Central Business District. The apartment has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travelers.
The apartment has one bedroom with a queen-sized bed and a pull-out sofa, comfortably accommodating up to four guests. The apartment comes equipped with a full kitchen, two flat-screen TVs, cable, Wi-Fi, a washer and dryer, and air conditioning.

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.

Destinations nearby

Best Winter Park, FL vacation rentals with a balcony

Lake House Pets Allowed - Winter Park, FL
9.8 197 reviews
Winter Park, FL
21/07 – 04/08
$449/nighttotal: $6286 (14 )

Lake House Pets Allowed

2 1
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.
Cozy Orlando Home Close To Parks, Dining, And Downtown Fun - Winter Park, FL
10 2 reviews
Winter Park, FL
03/09 – 08/09
$265/nighttotal: $1325 (5 )

Cozy Orlando Home Close To Parks, Dining, And Downtown Fun

2 2
apartment , Orlando
This Orlando apartment, situated in the Lawsona-Fern Creek neighbourhood, is a 13-minute walk (approximately 1km) from Lake Eola Park and offers easy access to attractions such as the Florida Mall and Universal Orlando Resort.
The two-bedroom, one-bathroom property sleeps six guests and features a fully equipped kitchen with dishwasher, a terrace, air conditioning, Wi-Fi, and a workspace, perfect for families or groups visiting the city.
Posada Tulum - Winter Park, FL
5.0 1 review
Winter Park, FL
02/08 – 04/08
$550/nighttotal: $1100 (2 )

Posada Tulum

1 6
house , Fairview Shores
This detached property in Fairview Shores, Orlando, is conveniently located approximately 9.3 kilometres from the Kia Centre and Church Street Station, with Camping World Stadium just 9.5 kilometres away.
This dwelling offers accommodation for up to 27 guests with one bedroom and two bathrooms, featuring air conditioning, a kitchen with a minibar, free Wi-Fi, a terrace, and a swimming pool with a Jacuzzi.
Walk Into Tropical Paradise - Pool - Gym - Hot Tub - Winter Park, FL
9.2 17 reviews
Winter Park, FL
17/06 – 23/06
$690/nighttotal: $4140 (6 )

Walk Into Tropical Paradise - Pool - Gym - Hot Tub

4 1
apartment , Altamonte Springs
This Altamonte Springs holiday home, conveniently located near Interstate 4, offers easy access to Orlando's theme parks and is within a short distance of Altamonte Springs' shopping and dining areas.
Sleeping up to nine guests, this four-bedroom, two-bathroom property boasts a private backyard with a pool, hot tub, mini-golf, and yard games, plus a fully equipped kitchen, home gym, and multiple large-screen TVs.

Best pet friendly Winter Park, FL vacation rentals

Among the 288 accommodations in Winter Park, FL, here are the 4 best pet friendly rentals

Bungalow On Quiet Street Close To Trendy Cafes, Pubs, And Parks. Dogs Welcome! - Winter Park, FL
10 36 reviews
Winter Park, FL
03/09 – 08/09
$239/nighttotal: $1195 (5 )

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

2 2
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.
3 Br Near Downtown| Hotub, Pool, Gazebo | Sleeps 7 - Winter Park, FL
9.5 54 reviews
Winter Park, FL
02/08 – 04/08
$361/nighttotal: $722 (2 )

3 Br Near Downtown| Hotub, Pool, Gazebo | Sleeps 7

1 6
apartment , Orlando
This three-bedroom, two-bathroom holiday home is situated near Orlando's Ivanhoe Village and Mills District, offering easy access (within 1.6km) to I-4, Dubsdread Golf Course, and AdventHealth, and approximately 17.7km from Downtown Orlando and the Dr. Phillips Center for the Performing Arts.
Sleeping up to eight guests, the property boasts a full kitchen, washer/dryer, high-speed Wi-Fi, a swimming pool, jacuzzi, and parking, plus a unique 'cowboy pool', all within a stylish interior featuring a neutral palette and turquoise accents.
Cozy Urban Flat Near Lake Eola - Winter Park, FL
9.6 61 reviews
Winter Park, FL
03/07 – 31/07
$99/nighttotal: $2772 (28 )

Cozy Urban Flat Near Lake Eola

1 2
apartment , Orlando
This one-bedroom Orlando apartment is located in downtown Orlando, within walking distance of Thornton Park's restaurants.
The self-catering flat sleeps two guests and includes a kitchen, air conditioning, and internet access; exploring Orlando's attractions is easy from this central location.
Private City Oasis - Winter Park, FL
9.5 85 reviews
Winter Park, FL
03/07 – 10/07
$177/nighttotal: $1239 (7 )

Private City Oasis

1 2
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.
©2026 cozycozy.com