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Winter Park, FL accommodations
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319 Lodgings in Winter Park, FL

Top-Rated Family Lodgings in Winter Park, FL

These family-friendly lodgings in Winter Park, FL offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.

Large, Beautiful, Very Comfortable One Bedroom On Small Lake - Winter Park, FL
9.9 226 reviews
Winter Park, FL
07/03 – 07/31
$263/nighttotal: $7364 (28 )

Large, Beautiful, Very Comfortable One Bedroom On Small Lake

1 2
apartment , Orlando
This family-friendly vacation home is located near downtown Orlando, just a mile from Lake Eola Park and the Orlando Regional Medical Center. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This 1-bedroom, 1-bathroom rental offers 500 square feet of living space, accommodating up to 2 guests. Amenities include a swimming pool, jacuzzi, sauna, spa, fitness center, tennis court, and a fully equipped kitchen, providing a relaxing and convenient experience.
Renovated Luxury 6000 Sqft Mansion In Downtown Orlando Sleep 14 Near Theme Parks - Winter Park, FL
9.6 19 reviews
Winter Park, FL
06/28 – 07/18
$1498/nighttotal: $29960 (20 )

Renovated Luxury 6000 Sqft Mansion In Downtown Orlando Sleep 14 Near Theme Parks

6 1
apartment , Orlando
This Orlando vacation home boasts a central location, a 15-minute walk from Lake Eola and the Dr. Phillips Center for the Performing Arts, and under 3 miles from Camping World Stadium and the Amway Center.
This 6,000-square-foot house features six bedrooms, five bathrooms, sleeps fourteen guests, and includes a private pool, spa, game room, and on-site water park.
New! Spacious Designer 2-bed/2.5-bath Townhome Near Downtown Orlando - Winter Park, FL
10 17 reviews
Winter Park, FL
06/17 – 06/23
$297/nighttotal: $1782 (6 )

New! Spacious Designer 2-bed/2.5-bath Townhome Near Downtown Orlando

2 1
apartment , Orlando
This Lancaster Park vacation home is conveniently located near Orlando Regional Medical Center (1.3 miles) and the Kia of Orlando dealership (2.6 miles), offering easy access to healthcare and shopping.
This 1,380-square-foot house features two bedrooms, three bathrooms, sleeps six guests, and includes a fully equipped kitchen, free WiFi, a patio, and an on-site playground.
Orlando Tropical Oasis - Winter Park, FL
9.9 72 reviews
Winter Park, FL
07/21 – 08/04
$267/nighttotal: $3738 (14 )

Orlando Tropical Oasis

1 1
apartment , Casselberry
This four-bedroom home in Maitland, Florida, is conveniently located about 30 minutes to an hour from both Orlando's theme parks and the beach. The property has earned excellent ratings for its location, cleanliness, and overall user experience.
This spacious rental sleeps up to 8 guests and is perfect for families or groups of friends. The apartment offers a private backyard, a screened-in patio, a fully equipped kitchen, air conditioning, Wi-Fi, and a swimming pool.

Best Winter Park, FL lodging with a pool

Among the 319 accommodations in Winter Park, FL, here are the 4 best ones with a pool

Lake House Pets Allowed - Winter Park, FL
9.8 197 reviews
Winter Park, FL
07/03 – 07/31
$306/nighttotal: $8568 (28 )

Lake House Pets Allowed

2 2
apartment , Orlando
This family-friendly vacation rental is located near downtown Orlando, within a mile of Lake Eola and its park, and within three miles of Camping World Stadium. This property has received excellent ratings for location, cleanliness, and overall experience.
This two-bedroom, two-bathroom home comfortably accommodates four guests. The house features a full kitchen, a swimming pool, a jacuzzi, a sauna, a spa, a fitness center, a tennis court, and a garden, offering a variety of amenities and activities for relaxation and entertainment.
Century Millenia - Winter Park, FL
9.0 128 reviews
Winter Park, FL
10/05 – 10/14
$518/nighttotal: $4662 (9 )

Century Millenia

2 4
apartment , Orlando
This Florida Center apartment rental is conveniently located less than 1.2 miles from Mall at Millenia and Orlando International Premium Outlets, and within 3 miles of Universal Orlando Resort and Universal CityWalk.
The unit offers free Wi-Fi, in-unit laundry, a swimming pool, and concierge service, providing easy access to major attractions and all the comforts of home.
* Beautiful Lakehouse With Pool And Movie Theater* - Winter Park, FL
9.9 97 reviews
Winter Park, FL
06/20 – 06/27
$585/nighttotal: $4095 (7 )

* Beautiful Lakehouse With Pool And Movie Theater*

1 6
apartment , Casselberry
This Casselberry vacation rental is conveniently located within walking distance of the Casselberry Golf Course and driving range, offering easy access to all of Orlando's attractions, including Downtown Orlando, theme parks, the springs, Cocoa/Daytona beaches, and Orlando & Sanford Airports. The apartment has earned excellent ratings for its user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The spacious home features five bedrooms and two bathrooms, comfortably accommodating up to 16 guests. Enjoy a private screened-in pool, lakefront beach area, water sports equipment, a movie theater room, a modern coffee bar, an outdoor shower, and HD TVs in every room.
Quiet And Safe Neighborhood Come To This Great Place With Lots Of Room For Relax - Winter Park, FL
9.4 3 reviews
Winter Park, FL
06/20 – 06/27
$184/nighttotal: $1288 (7 )

Quiet And Safe Neighborhood Come To This Great Place With Lots Of Room For Relax

2 6
apartment , Winter Park
This Winter Park rental is a 12-minute drive to the Kia Center and 22 minutes to the Florida Mall, offering convenient access to entertainment and shopping.
This 850-square-foot apartment accommodates up to six guests with two bedrooms and two bathrooms, featuring a full kitchen, air conditioning, complimentary Wi-Fi, and access to a communal pool and garden.

Frequently Asked Questions about accommodations in Winter Park, FL

  • What are the top attractions and must-see sites in Winter Park, FL?

    Winter Park is known for its beautiful parks and gardens, like the scenic Rollins College, the charming Mead Garden, and the stunning Kraft Azalea Garden. You can also visit the iconic Winter Park Scenic Boat Tour, which offers breathtaking views of the city's canals and waterways. And don't miss the charming shops and restaurants along Park Avenue, the heart of Winter Park.
  • What are the best accommodations in Winter Park, FL?

    Among the accommodations in Winter Park, FL, The Oasis W/pool Access En-suite #1, Modern Tropical House Heated Salt Pool and Sun Room are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Winter Park, FL?

    The Winter Park Sidewalk Art Festival is a must-see, showcasing local artists and their work. The annual Winter Park Autumn Art Festival is another popular event, featuring art, music, and food. For a festive experience, visit the Winter Park Christmas in the Park, a magical event with lights, music, and Santa Claus.
  • What are the best accommodations with a pool in Winter Park, FL?

  • What are the most convenient modes of transportation within Winter Park, FL?

    Winter Park is very walkable, especially in the downtown area. You can also rent a bike or use the SunRail, a commuter rail system that connects Winter Park to Orlando. If you prefer to drive, parking is available throughout the city, but be prepared for traffic during peak hours.
  • What are the best accommodations with a jacuzzi in Winter Park, FL?

  • What outdoor activities and adventures are popular in and around Winter Park, FL?

    Winter Park is a great place for outdoor enthusiasts. You can enjoy kayaking or paddleboarding on Lake Maitland, go for a hike in the Wekiwa Springs State Park, or play a round of golf at one of the many golf courses in the area. For a unique experience, visit the Albin Polasek Museum & Sculpture Gardens, featuring beautiful sculptures and gardens.
  • What are the best accommodations for families and kids in Winter Park, FL?

    The best accommodations for families and kids in Winter Park, FL are Sun Room , The Alfond Inn and The Delaney Hotel.

  • What types of accommodations are available in Winter Park, FL?

    You'll find a variety of accommodations in Winter Park, from cozy bed and breakfasts to luxurious hotels. There are also vacation rentals available, offering more space and privacy. Consider staying near Park Avenue for easy access to shops, restaurants, and attractions.
  • What are the best pet friendly accommodations in Winter Park, FL?

    The best pet friendly accommodations in Winter Park, FL are Modern Tropical House Heated Salt Pool, Sun Room and The Alfond Inn.

  • When is the best time to visit Winter Park, FL?

    The best time to visit Winter Park is during the spring and fall, when the weather is pleasant and the crowds are smaller. The summer months can be hot and humid, but the city offers plenty of indoor activities. Winter is a great time to enjoy the holidays and the beautiful Christmas lights.
  • What are the best accommodations with parking in Winter Park, FL?

    The Oasis W/pool Access En-suite #1, Modern Tropical House Heated Salt Pool and Sun Room are the best accommodations with parking in Winter Park, FL.

  • What local dishes and culinary experiences are a must-try in Winter Park, FL?

    Winter Park has a vibrant culinary scene. Be sure to try the fresh seafood at The Wine Room, the delicious Italian cuisine at Prato, or the innovative dishes at The Ravenous Pig. Don't forget to sample the local craft beers at the Winter Park Brewing Company.
  • In which part of Winter Park, FL should you consider renting accommodation?

    For easy access to shops, restaurants, and attractions, consider staying near Park Avenue. If you prefer a quieter setting, the areas around Lake Maitland or the Kraft Azalea Garden offer peaceful accommodations. For those who want to be close to the action, the downtown area provides a vibrant atmosphere.

Destinations nearby

Best Winter Park, FL accommodation with a garden

Winter Park Pearl 6 Min Drive To Historic Park Ave - Winter Park, FL
9.9 451 reviews
Winter Park, FL
08/02 – 08/04
$256/nighttotal: $512 (2 )

Winter Park Pearl 6 Min Drive To Historic Park Ave

1 6
apartment , Casselberry
Casselberry Cottage is a charming 3-bedroom, 1-bathroom cottage located in a quiet Winter Park neighborhood, just a 5-minute drive from the shops and restaurants of Park Avenue. The cottage has recently been remodeled and features a full kitchen with rustic butcher block counters and Zwilling J.A. Henckels knives, three 50-inch 4k smart TVs, and a private backyard with a charcoal grill. The cottage has received excellent ratings for its location, cleanliness, and user experience, and can accommodate up to 4 guests.
Stylish Newly Updated Home In Winter Park - Winter Park, FL
9.9 194 reviews
Winter Park, FL
08/02 – 08/04
$380/nighttotal: $760 (2 )

Stylish Newly Updated Home In Winter Park

1 6
apartment , Fairview Shores
This Fairview Shores apartment offers convenient access to I-4, placing Universal Studios, International Drive, and Disney World within a 20-40 minute drive.
Sleeping up to 10 guests, this two-bathroom rental boasts a fully equipped kitchen with modern appliances, a 65" Samsung smart TV, and a large backyard with a fire pit; nearby restaurants are a short walk away.
Close To The Action, Peaceful When You Return - Winter Park, FL
Winter Park, FL
06/20 – 06/27
$184/nighttotal: $1288 (7 )

Close To The Action, Peaceful When You Return

2 6
house , Orlando
This Orlando house is centrally located, offering proximity to downtown attractions like Church Street Station (1.1 miles) and Kia Center (1.3 miles), with easy access to major theme parks.
This 1000 square foot vacation home accommodates up to 11 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen, free WiFi, and a garden.
Fern Park Retreat - Winter Park, FL
9.9 61 reviews
Winter Park, FL
07/21 – 08/04
$120/nighttotal: $1680 (14 )

Fern Park Retreat

1 1
apartment , Maitland
This renovated 1958 guest house is located in Fern Park, just a short distance from the SunRail train station, offering easy access to Winter Park and downtown Orlando. The two-bedroom, one-bathroom home features a fully equipped kitchen, a fenced backyard, and a laundry room, perfect for a comfortable and relaxing stay for up to two guests.

Neighborhoods and points of interest in Winter Park, FL

Best Winter Park, FL accommodation with a kitchen

Cozy Guest House Close To Downtown Orlando - Winter Park, FL
9.7 185 reviews
Winter Park, FL
09/03 – 09/08
$111/nighttotal: $555 (5 )

Cozy Guest House Close To Downtown Orlando

1 2
house , Fairview Shores
This Winter Park guesthouse offers convenient access to Downtown Orlando and Downtown Winter Park (under 10 minutes), major theme parks (15-30 minutes), and beaches (within an hour).
The one-bedroom rental features a queen bed, queen sleeper sofa, full kitchen with fridge and microwave, air conditioning, parking, and accommodates up to three guests, with nearby restaurants and supermarkets within walking distance.
Sleeps 2 | Lake Eola |Downtown Orlando | Oasis - Winter Park, FL
9.8 34 reviews
Winter Park, FL
06/28 – 07/18
$112/nighttotal: $2240 (20 )

Sleeps 2 | Lake Eola |Downtown Orlando | Oasis

1 1
apartment , Orlando
This 1-bedroom guest suite is located in the historic Lake Eola Heights neighborhood of Orlando, a 2-minute walk to Lake Eola Park and within easy reach of downtown Orlando's dining, shopping, and the Dr. Phillips Center for the Arts.
This second-floor apartment accommodates up to 2 guests and features a fully equipped kitchen, air conditioning, and a garden, with the surrounding area being highly walkable and bike-friendly for local exploration.
Orlando Area 5/2 Pool Disney Universal Daytona - Winter Park, FL
9.5 94 reviews
Winter Park, FL
06/20 – 06/27
$376/nighttotal: $2632 (7 )

Orlando Area 5/2 Pool Disney Universal Daytona

5 6
apartment , Altamonte Springs
This Altamonte Springs rental is located a 15-minute drive from Orlando and a short distance from popular attractions like Disney World, Universal Studios, and Epcot. The property boasts excellent user, location, and cleanliness ratings.
This 5-bedroom, 2-bathroom home comfortably sleeps up to 16 guests and includes a private pool, a large fenced yard with a charcoal grill, a professional pool table, a regulation-size ping pong table, a fussball table, a domino table, a fully equipped kitchen, high-speed internet, a washer and dryer, and themed bedrooms.
Cheerful 3 Bedroom With A Spacious Shaded Yard - Winter Park, FL
9.8 128 reviews
Winter Park, FL
06/20 – 06/27
$264/nighttotal: $1848 (7 )

Cheerful 3 Bedroom With A Spacious Shaded Yard

1 6
apartment , Goldenrod
This mid-century home is located in Goldenrod, just a short drive from downtown Orlando, Park Ave, and UCF, making it a convenient base for exploring the area. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
This spacious house has three bedrooms and two bathrooms, comfortably accommodating up to 16 guests. Enjoy modern amenities like a full kitchen, washer and dryer, air conditioning, and a private yard perfect for outdoor gatherings.
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