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

Great Central Location - Winter Park, FL
8.0 1 review
Winter Park, FL
03/09 – 08/09
£131/nighttotal: £655 (5 )

Great Central Location

2 2
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.
The Bird House Spa Winter Park - Winter Park, FL
9.6 18 reviews
Winter Park, FL
03/07 – 10/07
£212/nighttotal: £1484 (7 )

The Bird House Spa Winter Park

1 2
apartment , Casselberry
This luxurious Maitland property, a short drive from Casselberry, offers easy access to Central Florida's theme parks and Winter Park's Park Avenue.
The 242-square-metre (2600 sq ft) holiday home boasts four bedrooms, three bathrooms, sleeps ten guests, and includes a gourmet kitchen, game room with pool table and air hockey, infrared sauna, hot tub, and multiple dining areas.
#1 Rated Neighborhood|.4 Mi. To Advent Hospital - Winter Park, FL
9.2 17 reviews
Winter Park, FL
03/07 – 31/07
£95/nighttotal: £2660 (28 )

#1 Rated Neighborhood|.4 Mi. To Advent Hospital

1 2
apartment , Orlando
This College Park bungalow, situated 0.6 km from AdventHealth Hospital and 1.1 km from Main Street College Park, offers a convenient location in Orlando's top-rated neighbourhood (2023 Orlando Weekly).
The two-bedroom, one-bathroom property sleeps four, includes a kitchen with dishwasher, and boasts a private fenced backyard, ample parking, a fitness centre, swimming pool, and is perfect for extended stays (minimum 28 days).
Cozy 4/2, King Beds, Pergola & Hot Tub, Local Pool! - Winter Park, FL
9.6 15 reviews
Winter Park, FL
03/07 – 10/07
£271/nighttotal: £1897 (7 )

Cozy 4/2, King Beds, Pergola & Hot Tub, Local Pool!

4 2
apartment , Casselberry
This apartment is located in Casselberry, just under 6 miles from Winter Park, less than 12 miles from downtown Orlando, and under 30 miles from I-Drive & Disney, making it a convenient base for exploring the area. It has received excellent user ratings, highlighting its appeal to travellers.
The property offers 144 square metres of space, accommodating up to 13 guests in its four bedrooms and two bathrooms. Amenities include a fully equipped kitchen, a private patio with a hot tub and pool, a dedicated kids' play area, a Marvel Arcade, and free high-speed Wi-Fi.

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.

Apartment ∙ 2 Bedrooms ∙ 4 Guests - Winter Park, FL
Winter Park, FL
10/07 – 18/07
£112/nighttotal: £896 (8 )

Apartment ∙ 2 Bedrooms ∙ 4 Guests

2 4
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.
*Travel Themed Property With Backyard Oasis* - Winter Park, FL
9.8 38 reviews
Winter Park, FL
10/07 – 18/07
£383/nighttotal: £3064 (8 )

*Travel Themed Property With Backyard Oasis*

6 4
apartment , Casselberry
This six-bedroom apartment is located in Maitland, a suburb of Orlando, just 15 kilometres from Casselberry and within walking distance of a Walmart Supercenter and various restaurants. The apartment is rated excellent by previous guests and offers a comfortable and convenient base for exploring the many attractions of Orlando.
The apartment spans 232 square metres and comfortably accommodates up to 14 guests. It features a private pool, an outdoor kitchen, a fire pit, a game room, a travel-themed design, and a separate one-bedroom "Castaway Island" apartment.
Elegant King Suite Downtown | Pool, Gym In City Ce - Winter Park, FL
10 9 reviews
Winter Park, FL
03/07 – 10/07
£129/nighttotal: £903 (7 )

Elegant King Suite Downtown | Pool, Gym In City Ce

1 2
apartment , Orlando
This one-bedroom apartment is located in Downtown Orlando, just a 5-minute walk from Wall Street Plaza and Church Street, and within 800 metres of Lake Eola, the Dr. Phillips Centre, and the Kia Centre.
This pet-friendly accommodation for four guests offers resort-style amenities including a swimming pool, fitness centre, and a rooftop deck, with Universal Studios 24 kilometres away and Walt Disney World 43 kilometres away.
Beautiful Flat In Winter Park - Winter Park, FL
Winter Park, FL
28/06 – 18/07
£80/nighttotal: £1600 (20 )

Beautiful Flat In Winter Park

1 1
apartment , Winter Park
This Winter Park flat provides excellent access to Orlando's main tourist spots, with major medical facilities and theme parks like Walt Disney World and Universal Orlando Resort a short drive away.
This property accommodates up to three guests and features a kitchen, air conditioning, and a swimming pool, making it ideal for exploring Central Florida's dining, shopping, and cultural attractions.

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

Thornton Park Oasis 1 Bedroom - Winter Park, FL
Winter Park, FL
28/06 – 18/07
£82/nighttotal: £1640 (20 )

Thornton Park Oasis 1 Bedroom

1 1
apartment , Orlando
This one-bedroom flat in Orlando's Thornton Park district is located 0.7 kilometres from the city centre, 1.9 kilometres from the Kia Centre, and 4 kilometres from Camping World Stadium, with Church Street Station a 19-minute walk away.
This 70 square metre apartment accommodates up to three guests and features complimentary WiFi, air conditioning, a private patio, and a fully equipped kitchen with a fridge and microwave oven.
Comfy & Cool, Kitchen/pool, Disney+ Near Orlando - Winter Park, FL
9.2 61 reviews
Winter Park, FL
28/06 – 18/07
£60/nighttotal: £1200 (20 )

Comfy & Cool, Kitchen/pool, Disney+ Near Orlando

1 1
apartment , Altamonte Springs
This one-bedroom apartment in Altamonte Springs is located just a few kilometres from the attractions of Orlando, in a peaceful neighbourhood with easy access to I-4 and SR-436. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is suitable for up to four guests and comes with a fully equipped kitchen, a screened porch, and access to a swimming pool. Guests can enjoy free Wi-Fi, a Roku TV, and keyless entry for a convenient and comfortable stay.
Tiny Unit In Cottage In The Middle Of Downtown - Winter Park, FL
Winter Park, FL
23/06 – 28/06
£65/nighttotal: £325 (5 )

Tiny Unit In Cottage In The Middle Of Downtown

1 2
house , Orlando
This studio apartment is situated 0.96 kilometres from Orlando's city centre, a 9-minute walk from Church Street Station and a 13-minute walk from the Kia Centre.
This property offers air conditioning, free Wi-Fi, and private parking, with a guest capacity of two people and a check-out time of 11:00 AM.
Den On Daniels - Modern Private Home With Balcony In Downtown Orlando - Winter Park, FL
9.0 4 reviews
Winter Park, FL
28/06 – 18/07
£130/nighttotal: £2600 (20 )

Den On Daniels - Modern Private Home With Balcony In Downtown Orlando

1 1
apartment , Orlando
This Orlando apartment, located in the Lake Davis-Greenwood neighbourhood, is less than 1.6km from Downtown Orlando and close to Universal Orlando Resort and Universal Studios Florida.
The 46 square metre flat features one bedroom, one bathroom, sleeps two guests, and includes a private balcony, kitchen with fridge and microwave, and amenities such as coffee, towels, and an Alexa device; kayaking, motor boating, and fishing are available nearby.

Best Winter Park, FL accommodations with a kitchen

Lake Eola View 1 Bedroom Thornton Park - Winter Park, FL
10 14 reviews
Winter Park, FL
28/06 – 18/07
£86/nighttotal: £1720 (20 )

Lake Eola View 1 Bedroom Thornton Park

1 1
apartment , Orlando
This Orlando apartment, situated in the South Eola district, offers lakefront views and is conveniently located near Thornton Park's restaurants and the Dr. Philips Center for the Performing Arts, with major attractions such as Universal Orlando Resort and the Florida Mall within a reasonable driving distance (distances vary depending on traffic).
The one-bedroom, one-bathroom flat sleeps two guests and includes a kitchen with a fridge and microwave, air conditioning, parking, internet access, and in-unit streaming services (Hulu, Netflix, and AT&T TV app).
Altamonte Oak Tree Haven - Winter Park, FL
9.8 248 reviews
Winter Park, FL
08/01 – 29/01
£64/nighttotal: £1344 (21 )

Altamonte Oak Tree Haven

2 2
apartment , Altamonte Springs
This self-contained apartment is situated in a peaceful residential neighbourhood in Altamonte Springs, just a short drive (around 3 kilometres) from the popular Altamonte Mall and the scenic Wekiva River. The accommodation has consistently received excellent ratings for its cleanliness, location, and user experience.
The apartment is a two-bedroom property with one bathroom, comfortably accommodating up to four guests. Enjoy a range of amenities including a private patio, a fully equipped kitchen, complimentary drinks and snacks, and a shaded parking space.
Modern 3/2 In Ivanhoe Village - Winter Park, FL
9.9 180 reviews
Winter Park, FL
08/01 – 29/01
£82/nighttotal: £1722 (21 )

Modern 3/2 In Ivanhoe Village

1 2
apartment , Orlando
This newly renovated three-bedroom duplex in Orlando's Ivanhoe Village offers easy access to the city's best restaurants and entertainment.
Sleeping eight guests, the property boasts a private patio with BBQ, fire pit, and hammock, plus a fully equipped kitchen, in-unit laundry, and secure keyless entry.
Orlando Guest Suite - Winter Park, FL
9.2 23 reviews
Winter Park, FL
03/07 – 31/07
£38/nighttotal: £1064 (28 )

Orlando Guest Suite

1 2
house , Azalea Park
This Azalea Park annex offers a private guesthouse experience with a separate entrance, conveniently situated 10 minutes from Camping World Stadium and a short drive from Orlando International Airport, Advent Health East Orlando, and the theme parks.
This one-bedroom, one-bathroom accommodation sleeps two guests and features a kitchenette with a fridge, freezer, microwave, and Keurig, with air conditioning and parking provided.
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