Best apartment offers in Winter Park, FL

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Winter Park, FL apartments
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321 Best apartments in Winter Park, FL

Best family friendly Winter Park, FL Holiday Apartments and Self Catering Accommodations

Among the 321 accommodations in Winter Park, FL, here are the 4 best family friendly holiday apartments

"The Mouse" + The "Comforts Of Home" - Winter Park, FL
9.6 85 reviews

"The Mouse" + The "Comforts Of Home"

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.
The Clementine Boho Home In Orlandos Food Scene - Winter Park, FL
9.6 25 reviews

The Clementine Boho Home In Orlandos Food Scene

apartment, Orlando
This Orlando guest house, situated in the Park Lake – Highland neighbourhood, offers easy access to Winter Park and is within a 32- to 56-kilometre radius of major theme parks such as Universal Orlando Resort, SeaWorld Orlando, and Walt Disney World Resort.
The self-contained unit sleeps five, features a kitchen with a fridge and microwave, a private backyard, and access to a tennis court, parking, and outdoor amenities including a barbecue and trampoline; nearby attractions include the Central Florida Fairgrounds and Camping World Stadium.
Apartment ∙ 4 Guests - Winter Park, FL
No reviews

Apartment ∙ 4 Guests

apartment, Orlando
This private studio in Orlando's College Park offers independent stays with its own entrance, located just 10 kilometres from Downtown Orlando, 15 kilometres from Universal Orlando Resort, and 25 kilometres from Walt Disney World Resort.
This family-friendly flat accommodates four guests with a queen bed, a fully equipped kitchen featuring a retro fridge and induction cooktop, air conditioning, and complimentary on-site parking for one vehicle, plus a damage waiver covering up to £400 in accidental damage.
2 Min To Park Ave | Charming Winter Park Bungalow - Winter Park, FL
9.8 87 reviews

2 Min To Park Ave | Charming Winter Park Bungalow

apartment, Fairview Shores
This apartment is located in Winter Park, a charming neighbourhood just 2 kilometres from Park Avenue and its diverse dining scene, and 40 kilometres from Orlando International Airport. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment can comfortably accommodate up to four guests and features a spacious and open layout. Guests can enjoy a peaceful outdoor patio, a well-equipped kitchen, air conditioning, a garden, a fitness centre, and parking.

Best Winter Park, FL holiday apartments with a kitchen

The Louie - Luxe 1br Condo Dt W/ Rooftop Pool, Gym - Winter Park, FL
9.8 11 reviews

The Louie - Luxe 1br Condo Dt W/ Rooftop Pool, Gym

apartment, Orlando
This Orlando apartment, ideally situated in a central location, offers easy access to Downtown Orlando, the Amway Center, and major theme parks such as Disney World and Universal Studios, all within a 8-24 km radius.
The one-bedroom, one-bathroom flat sleeps three guests and boasts a luxe industrial loft design, including a fully equipped kitchen, two 55" TVs, high-speed Wi-Fi, in-unit laundry, private parking, and access to a rooftop lounge, heated pool, and fitness centre.
Apartment| Downtown Orlando 10 Min & Disney 25 Min - Winter Park, FL
9.7 50 reviews

Apartment| Downtown Orlando 10 Min & Disney 25 Min

apartment, Fairview Shores
This modern one-bedroom apartment, perfect for four guests, is situated in Winter Park, Florida, a short drive (approximately 24km) from Downtown Orlando and Orlando International Airport, offering easy access to outlet malls and the Kia Center.
The self-catering flat includes a full kitchen, in-unit laundry, complimentary Wi-Fi, private entrance, and parking, ensuring a comfortable stay near Fairview Shores.
Historic Home Lake Eola Studio Thornton Park - Winter Park, FL
9.9 90 reviews

Historic Home Lake Eola Studio Thornton Park

apartment, Orlando
This Orlando studio apartment boasts a central location, offering convenient access to various attractions, although precise distances to specific landmarks remain unspecified.
The self-contained apartment sleeps two, features a full kitchen with fridge, freezer and microwave, and includes on-site parking; further details on its size and specific layout are unavailable.
Traveler's Dream: Refresh & Recharge Poolside - Winter Park, FL
9.2 13 reviews

Traveler's Dream: Refresh & Recharge Poolside

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.

Frequently asked questions about apartment rentals in Winter Park, FL

  • What are the must-see attractions for a 2 days stay in Winter Park, FL?

    For a short stay, you've got to see the beautiful Rollins College campus with its historic buildings and lush greenery. Then head to the charming Park Avenue district for some boutique shopping and a bite to eat at one of the many restaurants. Don't miss the chance to explore the scenic Winter Park Scenic Boat Tour along the waterways.
  • Which neighborhoods in Winter Park, FL are best for renting an apartment?

    For a good mix of convenience and charm, consider the areas around Park Avenue, the area around the Winter Park Village, or the more residential neighbourhoods of Baldwin Park and the area around the Winter Park Country Club. You'll find a good selection of apartments in these areas.
  • What are the top cultural and historical sites in Winter Park, FL?

    Winter Park is full of history! The Charles Hosmer Morse Museum of American Art has a fantastic collection of Tiffany glass, while the Albin Polasek Museum & Sculpture Gardens is a must-see for art lovers. For a taste of the past, visit the Winter Park Historical Museum, which showcases the city's rich heritage.
  • What makes Winter Park, FL unique or famous?

    Winter Park is known for its beautiful, tree-lined streets, charming shops, and its unique mix of history and modern amenities. The city's waterways, including the Winter Park Chain of Lakes, are a big part of its appeal, offering opportunities for boating, kayaking, and simply enjoying the scenery.
  • Where can you find the best local markets and street food in Winter Park, FL?

    The Winter Park Farmers' Market held every Saturday at the Winter Park Farmers' Market is a great place to find fresh produce, local crafts, and delicious food from local vendors. For a more casual experience, check out the food trucks that gather in the Park Avenue district on Fridays.
  • How is the public transportation system in Winter Park, FL?

    Winter Park has a decent public transport system, but you'll likely find yourself relying on your own car or ride-sharing services for most of your travels. The Lynx bus system does run through Winter Park, and there are a few SunRail stations located nearby.
  • Which seasonal events or festivals should apartment renters look forward to in Winter Park, FL?

    Winter Park comes alive with events throughout the year! The annual Winter Park Sidewalk Art Festival is a highlight, showcasing local artists and their work. Other popular events include the Winter Park Concours d'Elegance, the Winter Park Autumn Festival, and the Winter Park Christmas in the Park.
  • What amenities are typically included in apartments in Winter Park, FL?

    Apartments in Winter Park typically come with basic amenities like central air conditioning, in-unit laundry, and parking. Some newer buildings might offer additional features like swimming pools, fitness centres, and community spaces.
  • What leisure activities are available for relaxation in Winter Park, FL?

    For relaxation, Winter Park has plenty to offer. Take a stroll through the scenic Kraft Azalea Garden, enjoy a picnic at Mead Garden, or simply relax by the water at Lake Baldwin. There are also plenty of opportunities for outdoor activities, like kayaking, paddleboarding, and cycling.

Popular destinations

Best Winter Park, FL holiday apartments with air conditioning

Nebula Suite Galaxy Near Airport +Disney/universal - Winter Park, FL
9.6 90 reviews

Nebula Suite Galaxy Near Airport +Disney/universal

apartment, Azalea Park
This Azalea Park studio apartment boasts a galaxy-themed interior and is located approximately 40km from Walt Disney World Resort, 40km from Universal Orlando Resort, and 40km from SeaWorld Orlando.
The self-catering apartment sleeps four guests, includes a kitchenette with a Star Wars toaster and coffee maker, a smart TV with Netflix and Hulu, and offers self check-in.
Beautiful Flat In Winter Park - Winter Park, FL
10 1 review

Beautiful Flat In Winter Park

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.
Historic Home-  Downtown Orlando - Winter Park, FL
9.5 70 reviews

Historic Home- Downtown Orlando

apartment, Orlando
This spacious two-bedroom apartment, situated near Lake Formosa in Orlando, Florida, is approximately 0.5 km from Interstate 4, offering easy access to both Walt Disney World and Daytona Beach, and is within walking distance of the Orlando Science Center and Mennello Museum of American Art.
The self-contained flat, located in a historically significant 1927 Mediterranean Revival home, sleeps two guests and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, parking, and benefits from a peaceful setting adjacent to a jogging trail.
Spacious Private & Lovely - Winter Park, FL
9.4 29 reviews

Spacious Private & Lovely

apartment, Winter Park
This Winter Park apartment, perfect for up to four guests, offers convenient access to local attractions, though precise distances to Park Avenue, Central Park, and the Morse Museum of American Art are unavailable.
The one-bedroom, one-bathroom flat features a spacious and serene layout, including a kitchen, air conditioning, internet, parking and allows pets; further details on interior design and specific amenities are not provided.

Best pet-friendly Winter Park, FL holiday apartments

Among the 321 accommodations in Winter Park, FL, here are the 4 best pet friendly holiday apartments

Lakefront House W/ Pool Near Downtown Orlando. Spacious 4-bedroom 3 Full Bath - Winter Park, FL
9.0 7 reviews

Lakefront House W/ Pool Near Downtown Orlando. Spacious 4-bedroom 3 Full Bath

apartment, Orlando
This lakefront villa in Orlando's Dover Shores West neighbourhood offers peaceful views of Lake Giles, situated just minutes from downtown Orlando's shops and restaurants, and a 32-kilometre drive to Universal Studios and a 48-kilometre drive to Walt Disney World.
This spacious 196-square-metre residence accommodates up to seven guests across four bedrooms, featuring a private screened-in swimming pool, a modern kitchen, a dedicated office space, and a living room with a 65-inch Fire Stick TV.
Riviere 2br Apartment Pet Friendly Oasis Sleeps 6 Close To Epic Universe Pool & Gym - Winter Park, FL
No reviews

Riviere 2br Apartment Pet Friendly Oasis Sleeps 6 Close To Epic Universe Pool & Gym

apartment, Orlando
This flat is located in Orlando's International Drive District, offering easy access to Orlando Outlet Marketplace and Orlando International Premium Outlets within a 15-minute walk, and is less than 5 kilometres from Universal Orlando Resort and Universal Studios Florida.
This pet-friendly accommodation provides air conditioning, an outdoor swimming pool, and complimentary self-parking, with a check-out time of 12:00 PM.
Stylish Downtown King Suite | Luxury Stay W/ Pool - Winter Park, FL
10 28 reviews

Stylish Downtown King Suite | Luxury Stay W/ Pool

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.
Beautiful 1-bedroom House With Ac In Welcoming Orlando - Winter Park, FL
No reviews

Beautiful 1-bedroom House With Ac In Welcoming Orlando

apartment, Rio Pinar
This apartment in Rio Pinar is situated a 4-minute drive from Country Club Rio Pinar and 5 minutes from Ventura Country Club, with Lake Eola Park 12 minutes away and Tinker Field 15 minutes away by car.
This pet-friendly flat accommodates up to six guests, offering air conditioning, Wi-Fi, a dryer, and basic toiletries, and is conveniently located for access to Florida Mall, Orlando International Premium Outlets, Universal Orlando Resort, and Universal Epic Universe.
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