Places to stay in Winter Park, FL

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Winter Park, FL place to stay
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319 Best places to stay in Winter Park, FL

Best family friendly Winter Park, FL lodging

Among the 319 accommodations in Winter Park, FL, here are the 4 best for families

Close To The Action, Peaceful When You Return - Winter Park, FL
Winter Park, FL
28/06 – 01/07
£147/nighttotal: £441 (3 )

Close To The Action, Peaceful When You Return

2 4
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.
Adorable 1-bedroom Home W/ Full Kitchen & Parking - Sleeps 4 - Winter Park, FL
9.6 162 reviews
Winter Park, FL
28/06 – 01/07
£134/nighttotal: £402 (3 )

Adorable 1-bedroom Home W/ Full Kitchen & Parking - Sleeps 4

1 4
apartment , Orlando
This one-bedroom apartment is located in Colonialtown South, just 800 metres from Lake Eola and within 5 kilometres of the Kia Center and Camping World Stadium. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 73 square metres and includes a fully equipped kitchen, a terrace, and a garden. It also offers amenities like free Wi-Fi, parking, air conditioning, and a designated smoking area, making it a comfortable and convenient base for exploring Orlando.
8th Green Cottage  - A Relaxing Oasis In The City - Winter Park, FL
9.8 195 reviews
Winter Park, FL
28/07 – 01/08
£126/nighttotal: £504 (4 )

8th Green Cottage - A Relaxing Oasis In The City

1 2
house , Orlando
The 8th Green Cottage is situated in a peaceful neighbourhood near the historic Dubsdread golf course, just 5 kilometres from downtown Orlando and within easy reach of Disney, Universal, and SeaWorld via the I4. The property has received excellent ratings for user experience, location, and cleanliness.
This 2-bedroom, 1-bathroom guest house comfortably accommodates up to 4 guests and offers a private driveway, entrance, and fenced-in yard. The cottage includes a well-equipped kitchen, a dedicated play arcade, access to streaming services, and a relaxing atmosphere, making it a perfect choice for families or groups of friends.
3-bedroom Peaceful Longwood Home  Minutes To Attractions - Netflix - Location - Winter Park, FL
10 3 reviews
Winter Park, FL
10/07 – 18/07
£125/nighttotal: £1000 (8 )

3-bedroom Peaceful Longwood Home Minutes To Attractions - Netflix - Location

3 4
apartment , Longwood
This Longwood flat is situated in a quiet residential area, offering easy access to local dining, shopping, golf courses, and is a short drive to Orlando's theme parks and the downtown area, with nearby parks and nature preserves for outdoor pursuits.
This family-friendly accommodation sleeps up to 8 guests across three queen-sized bedrooms and features a fully equipped kitchen with a microwave oven and dishwasher, air conditioning, and parking, with a check-out time of 11:00 AM.

Discover Places to Stay with a Pool in Winter Park, FL

Enjoy a swim whenever the mood strikes, as every accommodation in Winter Park, FL comes with a private on-site pool.

Florida Vacation With Pool Fun For Families - Winter Park, FL
9.4 42 reviews
Winter Park, FL
28/07 – 01/08
£151/nighttotal: £604 (4 )

Florida Vacation With Pool Fun For Families

4 2
apartment , Casselberry
This charming three-bedroom house is located in Casselberry, just 5km from Altamonte Mall and within 10km of Cranes Roost Park and Red Bug Lake Park, offering easy access to shopping and outdoor activities. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The house comfortably accommodates up to 7 guests and provides a fully equipped kitchen, a private pool, a garden with barbecue facilities, and free Wi-Fi. Enjoy the Florida sunshine with al fresco dining and relax by the pool, while exploring the nearby golf courses and parks.
Upscale King Suite In The Heart Of Orlando W/ Pool - Winter Park, FL
10 22 reviews
Winter Park, FL
28/07 – 01/08
£131/nighttotal: £524 (4 )

Upscale King Suite In The Heart Of Orlando W/ Pool

1 2
apartment , Orlando
This one-bedroom flat in Orlando, Florida, is located 6.4 kilometres from Universal Studios and Islands of Adventure and 43.5 kilometres from Walt Disney World Resort, with downtown nightlife, dining, and live music venues a short walk away.
This pet-friendly apartment offers accommodation for four guests, featuring a fully equipped kitchen with stainless steel appliances, air conditioning, a swimming pool, fitness centre, and in-unit laundry facilities.
Stylish Downtown King Suite | Luxury Stay W/ Pool - Winter Park, FL
10 14 reviews
Winter Park, FL
14/08 – 21/08
£101/nighttotal: £707 (7 )

Stylish Downtown King Suite | Luxury Stay W/ Pool

1 2
apartment , Orlando
This modern one-bedroom apartment in Orlando, Florida, is ideally situated for theme park access, with Universal Studios 24 kilometres away, Epic Universe 27 kilometres away, and Walt Disney World 43 kilometres away, while downtown attractions like the Dr. Phillips Centre and Kia Centre are within a 1.6-kilometre radius.
This pet-friendly apartment offers resort-style amenities including a swimming pool, a fitness centre, and a rooftop deck, featuring a fully-equipped kitchen with stainless steel appliances, a queen-size sofa bed, a king-size bed in the master bedroom, and an in-unit washer and dryer, accommodating up to four guests.
Pool Home Near Parks, Airport, & Hospitals - Winter Park, FL
9.9 17 reviews
Winter Park, FL
28/06 – 18/07
£153/nighttotal: £3060 (20 )

Pool Home Near Parks, Airport, & Hospitals

3 1
apartment , Orlando
This Orlando Airbnb, near major theme parks, Downtown Orlando, and outlet malls, offers convenient access to Walt Disney World Resort and Universal Orlando Resort, with beaches approximately 64km away.
This self-catering property sleeps four guests in two bedrooms with queen-size beds and en-suite TVs, boasting a private pool, Jacuzzi, and all mod cons including a dishwasher and air conditioning.

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 full of charm! You've got to visit the iconic Morse Museum of American Art, home to the largest collection of Louis Comfort Tiffany works. Then there's the scenic Rollins College, with its beautiful architecture and lush gardens. And don't forget the charming Winter Park Scenic Boat Tour on the canals, offering stunning views of the city.
  • What are the best places to stay in Winter Park, FL?

    Among the places to stay in Winter Park, FL, The Oasis W/pool Access En-suite #1, Modern Tropical Pool Home and Sun Room are the most popular ones.

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

    Winter Park is alive with events! The Winter Park Sidewalk Art Festival is a must-see, showcasing local artists and their work. For a festive experience, visit the Winter Park Christmas in the Park, filled with lights, music, and holiday cheer. And if you're around in March, the Winter Park Concours d'Elegance, a classic car show, is a real treat.
  • What are the best places to stay with a pool in Winter Park, FL?

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

    Getting around Winter Park is a breeze! You can easily walk or bike along the beautiful streets and paths. If you're venturing further, the Winter Park SunRail, a commuter rail line, connects you to other parts of the city. And of course, there are plenty of taxis and ride-sharing services available.
  • What are the best places to stay with a jacuzzi in Winter Park, FL?

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

    Winter Park is a haven for outdoor enthusiasts! The scenic Wekiwa Springs State Park offers hiking, kayaking, and swimming. You can also enjoy a leisurely stroll through the beautiful Mead Garden, or take a bike ride along the scenic Cady Way Trail. And for a more adventurous experience, try zip-lining at the Tree Trek Adventure Park.
  • What are the best places to stay for families and kids in Winter Park, FL?

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

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

    Winter Park has a range of accommodation options to suit every budget. From charming bed and breakfasts to luxurious hotels, you'll find something to fit your needs. There are also many vacation rentals available, offering a more home-like experience. And for a unique stay, consider the historic Alfond Inn, known for its art collection and elegant atmosphere.
  • What are the best pet friendly places to stay in Winter Park, FL?

    The best pet friendly places to stay in Winter Park, FL are Modern Tropical Pool Home , Sun Room and The Delaney Hotel.

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

    Winter Park is a lovely destination year-round. The weather is generally pleasant, with warm temperatures and plenty of sunshine. However, if you're looking for milder temperatures, the best time to visit is during the spring (March-May) or fall (September-November). The summer months (June-August) can be quite hot and humid.
  • What are the best places to stay with parking in Winter Park, FL?

    The Oasis W/pool Access En-suite #1, Modern Tropical Pool Home and Sun Room are the best places to stay 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 Bar, or indulge in a delicious brunch at The Ravenous Pig. For a taste of local flavour, visit the Winter Park Farmers' Market, where you can sample fresh produce and artisan goods. And don't forget to grab a scoop of ice cream at the iconic Kelly's Homemade Ice Cream.
  • In which part of Winter Park, FL should you consider renting accommodation?

    For a central location, the Park Avenue area is ideal. It's within walking distance of many shops, restaurants, and attractions. If you prefer a more residential setting, the areas around the Rollins College campus or the Winter Park Village are great options. And for those seeking a waterfront experience, the homes around the canals offer stunning views.

Destinations nearby

Best Winter Park, FL accommodations with a garden

The Guest House Orlando - Winter Park, FL
10 16 reviews
Winter Park, FL
28/06 – 18/07
£160/nighttotal: £3200 (20 )

The Guest House Orlando

1 1
apartment , Orlando
This Orlando guesthouse is situated in a peaceful, wooded neighbourhood, offering convenient access to the city's attractions, though precise distances aren't specified.
Sleeping up to five guests, the self-catering property features two bedrooms, one bathroom with a walk-in shower, a full kitchen with modern appliances, a spacious dining area, and a large garden with a deck – perfect for families.
Cozy Home 5min To Park Ave And Downtown Orlando - Winter Park, FL
9.7 84 reviews
Winter Park, FL
28/07 – 01/08
£123/nighttotal: £492 (4 )

Cozy Home 5min To Park Ave And Downtown Orlando

1 2
apartment , Fairview Shores
This Fairview Shores apartment, situated 5 minutes from Park Avenue and under 7 minutes (approx. 8 km) from Orlando city centre, offers easy access to restaurants, boutiques, and cafes.
The two-bedroom, one-bathroom flat sleeps six, features a 50" Roku TV, dedicated office space, private patio, and a fully equipped kitchen including a dishwasher; parking is also provided.
Hot Tub, Fire Pit, Private Backyard, King Bed - Winter Park, FL
9.8 222 reviews
Winter Park, FL
14/08 – 21/08
£122/nighttotal: £854 (7 )

Hot Tub, Fire Pit, Private Backyard, King Bed

2 2
apartment , Azalea Park
This Azalea Park house, conveniently located near Downtown Orlando, the University of Central Florida (UCF), and Orlando International Airport (approximately 16-24 km from each), offers easy access to major attractions and theme parks.
The two-bedroom, one-and-a-half-bathroom property sleeps up to eight guests, boasting a fully equipped kitchen, private backyard with hot tub and fire pit, multiple smart TVs, and shared laundry facilities, plus three off-street parking spaces.
Centrally Located Orlando Home - Winter Park, FL
9.6 111 reviews
Winter Park, FL
28/06 – 01/07
£130/nighttotal: £390 (3 )

Centrally Located Orlando Home

1 4
apartment , Fern Park
This stylish three-bedroom house in Fern Park, a quiet Orlando suburb, is located approximately 15-25 km from Full Sail University, Rollins College, and downtown Orlando.
The 3-bedroom, 2-bathroom property sleeps six guests and features a fully equipped kitchen with stainless steel appliances, a garden, parking, keyless entry, and is within walking distance of Kewanee Park; a washer/dryer is available at an extra cost.

Best Winter Park, FL accommodations with a kitchen

City Charmer - Winter Park, FL
9.8 110 reviews
Winter Park, FL
10/07 – 18/07
£101/nighttotal: £808 (8 )

City Charmer

1 4
apartment , Orlando
This half-duplex is situated in Baldwin Park, a peaceful neighbourhood in Orlando, just a short walk from local shops, restaurants, and a grocery store, and only 16 kilometres from Orlando International Airport. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The property offers two bedrooms and two bathrooms, comfortably accommodating up to four guests. It features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, a garden, parking, and air conditioning, as well as internet access for your convenience.
Traveler's Dream: Refresh & Recharge Poolside - Winter Park, FL
9.4 11 reviews
Winter Park, FL
28/06 – 18/07
£71/nighttotal: £1420 (20 )

Traveler's Dream: Refresh & Recharge Poolside

1 1
apartment , Casselberry
This Casselberry flat is conveniently located approximately 3.5 km from Secret Lake Park and 4.5 km from Red Bug Lake Park, offering easy access to outdoor recreation.
The one-bedroom, one-bathroom apartment sleeps two guests and features a private pool, free Wi-Fi, a fully equipped kitchen with fridge and microwave, a smart TV, and access to a community pool; Winter Park Village and Altamonte Mall are within a 10 km radius.
Studio In Altamonte Spring - Winter Park, FL
10 1 review
Winter Park, FL
28/06 – 18/07
£89/nighttotal: £1780 (20 )

Studio In Altamonte Spring

1 1
studio , Altamonte Springs
This Altamonte Springs studio apartment is located 16-17.7 kilometres from Orlando's Camping World Stadium and Kia Centre, and 17.7 kilometres from Church Street Station.
This 70 square metre flat offers accommodation for up to seven guests with a fully equipped kitchen, air conditioning, free WiFi, and private parking, alongside a garden and bicycle parking facilities.
Charming Heated Pool Home In Altamonte Springs - Winter Park, FL
9.6 135 reviews
Winter Park, FL
10/07 – 18/07
£164/nighttotal: £1312 (8 )

Charming Heated Pool Home In Altamonte Springs

3 4
apartment , Altamonte Springs
This house is located in Altamonte Springs, just 5 kilometres from Altamonte Mall, Maitland Art Center, and Cranes Roost Park, making it easy to explore the area. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The property is a 3-bedroom, 2-bathroom house with a floor area of 153 square metres, comfortably accommodating up to 6 guests. This family-friendly home offers a range of amenities including a swimming pool, terrace, garden, and parking, as well as a fully equipped kitchen and air conditioning for a comfortable stay.
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