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

Quiet Retreat 15 Minutes From Downtown Orlando, Orlando Airport International! - Winter Park, FL
9.6 24 reviews
Winter Park, FL
10/07 – 18/07
£189/nightTotal: £1512 (8 )

Quiet Retreat 15 Minutes From Downtown Orlando, Orlando Airport International!

3 4
apartment , Azalea Park
Golden Cove Rental is situated in Azalea Park, a peaceful residential neighbourhood in Orlando, just 15km from Orlando International Airport, Interstate 4, and the city centre. This apartment has received very good user ratings, making it a popular choice for travellers.
This three-bedroom, two-bathroom property can accommodate up to 10 guests, making it ideal for families or groups. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a tennis court, and parking.
Lake House Pets Allowed - Winter Park, FL
9.8 197 reviews
Winter Park, FL
28/06 – 01/07
£264/nightTotal: £792 (3 )

Lake House Pets Allowed

2 4
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.
Renovated Luxury 6000 Sqft Mansion In Downtown Orlando Sleep 14 Near Theme Parks - Winter Park, FL
9.6 19 reviews
Winter Park, FL
28/06 – 18/07
£1014/nightTotal: £20280 (20 )

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

6 1
apartment , Orlando
This six-bedroom Orlando holiday home is centrally located, within a 2.4km walk of Lake Eola and the Dr Phillips Center for the Performing Arts, and under 5km from Camping World Stadium and the Kia Forum.
The 557 square metre property boasts a private water park, on-site arcade, and sleeps up to 14 guests, offering a fully equipped kitchen, swimming pool, spa, and a relaxing garden with a living plant wall.
Nook Haven | Glamping Retreat •Pool • Hot Tub - Winter Park, FL
9.9 77 reviews
Winter Park, FL
28/07 – 01/08
£98/nightTotal: £392 (4 )

Nook Haven | Glamping Retreat •Pool • Hot Tub

1 2
glamping , Goldenrod
This motorhome is located in a quiet Winter Park cul-de-sac, approximately 7 minutes from Park Avenue's dining and shopping, and 20 minutes from Universal Orlando Resort.
The "Glamping Rv*free Parking *Private Patio*sleeps 5" offer provides a 140 sq ft temperature-controlled RV with a queen bed, twin bunks, and kitchenette, alongside access to a shared pool, hot tub, grill, and fire pit, all within a private 200 sq ft patio for up to 5 guests.

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.

Virelli Apartments Upscale King Suite In The Heart Of Orlando W Pool - Winter Park, FL
10 1 review
Winter Park, FL
28/06 – 01/07
£226/nightTotal: £678 (3 )

Virelli Apartments Upscale King Suite In The Heart Of Orlando W Pool

1 4
apartment , Orlando
This downtown Orlando flat offers convenient access to attractions, being a 1.3-kilometre walk from the Kia Centre and 1.1 kilometres from Church Street Station, with Camping World Stadium a short drive away.
This 74 square metre apartment accommodates up to seven guests with one bedroom and one bathroom, featuring air conditioning, complimentary WiFi, on-site parking, a fully equipped kitchen, and access to a communal swimming pool and garden.
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
23/06 – 28/06
£152/nightTotal: £760 (5 )

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

2 2
apartment , Winter Park
This Winter Park flat is situated 1.9 kilometres from the Kia Centre and 3.5 kilometres from The Florida Mall, offering convenient access to local attractions.
This 79 square metre apartment accommodates up to six guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, complimentary Wi-Fi, on-site parking, and access to a communal swimming pool and barbecue area.
Orlando Area Pool Home In Maitland - Winter Park, FL
9.9 183 reviews
Winter Park, FL
28/06 – 01/07
£275/nightTotal: £825 (3 )

Orlando Area Pool Home In Maitland

1 4
apartment , Altamonte Springs
This Maitland holiday home is located just 5km from Altamonte Mall, Cranes Roost Park, and RDV Sportsplex, placing you within easy reach of the area's attractions. It has received excellent ratings for location, cleanliness, and overall user experience.
The property offers 167 square metres of living space, comfortably accommodating families or groups. You'll have access to a range of amenities including a private pool, a fenced garden, a fireplace, and barbecue grills, as well as a fully equipped kitchen and free Wi-Fi.
Modern Resort-style Stay - Winter Park, FL
9.6 65 reviews
Winter Park, FL
28/06 – 01/07
£155/nightTotal: £465 (3 )

Modern Resort-style Stay

2 4
apartment , Orlando
This smoke-free apartment building is situated in Ventura, close to Ventura Country Club, just a short distance from Lake Conway and Hoffner Plaza Shopping Center. It has received excellent user ratings, making it a popular choice for travellers. The two-bedroom apartment comfortably accommodates up to four guests and offers a range of amenities, including a swimming pool, jacuzzi, and a terrace or balcony. Guests can also enjoy a fully equipped kitchen, free Wi-Fi, and a smart TV, along with a washing machine and dryer.

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

Yale House In College Park 2 Mi From Downtown - Winter Park, FL
9.9 115 reviews
Winter Park, FL
28/06 – 18/07
£185/nightTotal: £3700 (20 )

Yale House In College Park 2 Mi From Downtown

1 1
apartment , Orlando
This charming apartment is located in a peaceful neighbourhood just 2 kilometres from downtown Orlando, close to shops, restaurants, and a grocery store. It has received excellent ratings for location, cleanliness, and user experience.
The two-bedroom flat can accommodate up to four guests and features a spacious living room, a fully equipped kitchen, and a dedicated workspace. It also offers a range of amenities including a Jacuzzi, a garden, a fitness centre, and a private gym in a detached garage.
Alluring 2bd/2ba In East Orlando. - Winter Park, FL
9.4 16 reviews
Winter Park, FL
28/06 – 01/07
£157/nightTotal: £471 (3 )

Alluring 2bd/2ba In East Orlando.

2 4
apartment , Orlando
This Orlando property is conveniently located near Ventura Country Club, with Rio Pinar Country Club and The Plaza Theatre within a 9.6km radius.
This two-bedroom, two-bathroom house sleeps four guests and boasts a fully equipped kitchen, private swimming pool, terrace, garden, on-site fitness centre, and WiFi; housekeeping is available on request.
"The Mouse" + The "Comforts Of Home" - Winter Park, FL
9.6 84 reviews
Winter Park, FL
10/07 – 18/07
£103/nightTotal: £824 (8 )

"The Mouse" + The "Comforts Of Home"

2 4
apartment , Orlando
This two-bedroom apartment is conveniently located in Ventura, Orlando, just six miles from Orlando International Airport and 20-30 minutes from Disney World, Sea World, and Universal Studios. It has received excellent user ratings, making it a popular choice for travellers. This 79 square metre apartment comfortably sleeps six guests. The apartment features a fully equipped kitchen, a private patio, a swimming pool, a Jacuzzi, and a garden, offering a relaxing and enjoyable stay.
Downtown Private Efficiency Lake Eola Central Business District - Winter Park, FL
9.4 65 reviews
Winter Park, FL
28/07 – 01/08
£89/nightTotal: £356 (4 )

Downtown Private Efficiency Lake Eola Central Business District

1 2
apartment , Orlando
This studio apartment is located in downtown Orlando, just a short walk from Lake Eola, the Dr. Philips Center, Amway Arena, and Publix. It has received excellent user ratings, making it a popular choice for travellers.
The apartment is compact, measuring just 14 square metres, and includes a kitchenette, a private entrance, and a comfortable bedroom. It also offers access to streaming services, air conditioning, and parking.

Best Winter Park, FL accommodations with a kitchen

The Tiny Cottage In The Springs/ Central Fl - Winter Park, FL
9.0 38 reviews
Winter Park, FL
28/06 – 01/07
£121/nightTotal: £363 (3 )

The Tiny Cottage In The Springs/ Central Fl

2 4
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.
Cozy Guest House Close To Downtown Orlando - Winter Park, FL
9.7 191 reviews
Winter Park, FL
28/07 – 01/08
£87/nightTotal: £348 (4 )

Cozy Guest House Close To Downtown Orlando

1 2
house , Fairview Shores
This Winter Park guest house offers a prime location, a short 9.6km drive from Rollins College and under 16km from both Orlando and Winter Park city centres.
The self-catering property sleeps up to four guests in one bedroom with one bathroom, featuring a queen bed and a queen sleeper sofa, plus a kitchen equipped with a fridge and microwave, air conditioning, parking and excellent guest reviews.
Cute Guest House In Winter Park Minutes From Downtown In Car - Winter Park, FL
9.6 307 reviews
Winter Park, FL
28/06 – 18/07
£86/nightTotal: £1720 (20 )

Cute Guest House In Winter Park Minutes From Downtown In Car

1 1
apartment , Fairview Shores
This charming studio apartment is situated just a short drive from the Park Ave strip and Winter Park Village, offering easy access to shopping, dining, and entertainment. Guests consistently rate the property excellent for its location, cleanliness, and overall experience.
The studio is compact and comfortable, measuring 30 square metres and accommodating up to two guests. It includes modern amenities such as a kitchenette, refrigerator, air conditioning, smart TV, Wi-Fi internet, a queen-size bed, and a private bathroom with complimentary toiletries.
Mills House @Wp. Sleeps 10 Renovated. Queen Beds - Winter Park, FL
9.5 232 reviews
Winter Park, FL
28/06 – 01/07
£153/nightTotal: £459 (3 )

Mills House @Wp. Sleeps 10 Renovated. Queen Beds

1 4
apartment , Fairview Shores
This Fairview Shores house, located minutes from Lake Eola and Park Avenue in Winter Park, offers easy access to Mills 50 and major highways, with Orlando's theme parks approximately 40km away.
Sleeping up to 11 guests, this three-bedroom property boasts a fully equipped kitchen, a Roku-enabled TV, a fenced backyard with BBQ, and free parking for 3-4 vehicles; a master suite includes an ensuite bathroom and washer-dryer.
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