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

Renovated Peaceful Luxury Walk To Mall Park Publix - Winter Park, FL
9.0 22 reviews

Renovated Peaceful Luxury Walk To Mall Park Publix

apartment, Altamonte Springs
This Altamonte Springs holiday home is conveniently located less than 1.6km from Altamonte Mall and Cranes Roost Park, and around 3.2km from Sanlando Park.
The one-bedroom, one-bathroom property sleeps four guests and offers a fully equipped kitchen, in-unit laundry, free Wi-Fi, a smart TV, and access to an on-site fitness centre.
Casa Winter Park - Winter Park, FL
9.8 126 reviews

Casa Winter Park

apartment, Winter Park
This family-friendly house is situated in Winter Park, just 3km from Full Sail University and Albin Polasek Museum and Sculpture Gardens, and within 5km of Kraft Azalea Gardens and Winter Park Village. The property is highly rated by guests, with excellent reviews praising its comfortable and well-equipped nature.
This 279 square metre house is perfect for families, with 4 bedrooms and 4 bathrooms, comfortably accommodating up to 8 guests. Amenities include a private pool, a garden, a terrace and parking, along with a fully equipped kitchen and free Wi-Fi, making it ideal for a relaxing and enjoyable stay.
Dog-friendly Apt W/ Fenced Yard In Winter Park - Winter Park, FL
9.8 23 reviews

Dog-friendly Apt W/ Fenced Yard In Winter Park

apartment, Goldenrod
This Goldenrod flat is situated in Winter Park, offering convenient access to Walt Disney World and downtown Winter Park, with the airport nearby and the coast approximately 72 kilometres away.
This 60 square metre apartment accommodates up to six guests with two bedrooms, a well-equipped kitchenette, air conditioning, free WiFi, and a small fenced garden, ideal for pets, with nearby attractions including the Winter Park Tennis Centre and Dubsdread Golf Course.
Your Home Away From Home - Winter Park, FL
9.6 22 reviews

Your Home Away From Home

apartment, Goldenrod
This three-bedroom flat in a quiet Goldenrod district offers easy access to local attractions, with the Goldenrod Museum located 1.2 kilometers away and the Goldenrod Shopping Centre just 800 meters from your door.
This family-friendly property accommodates up to eight guests and features a private patio, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, and on-site parking, making it ideal for a comfortable stay.

Best Winter Park, FL holiday apartments with a kitchen

Treasure Of Winter Park - Winter Park, FL
9.6 5 reviews

Treasure Of Winter Park

apartment, Winter Park
This Winter Park flat is centrally located, within walking distance of local restaurants and parks.
The one-bedroom, one-bathroom apartment sleeps two guests, offering a freshly renovated modern space with a fully equipped kitchen, fast internet, and access to a lakeside pool and park; free parking is also provided.
Last Minute Deals End Soon, Orlando Home Pool Dock - Winter Park, FL
10 258 reviews

Last Minute Deals End Soon, Orlando Home Pool Dock

apartment, Goldenrod
This single-storey house is situated in East Orlando, just 12 minutes from the University of Central Florida and 40 minutes from Orlando International Airport. It has received excellent user, location, and cleanliness ratings.
The property spans 149 square metres and comfortably accommodates up to 8 guests in its four bedrooms and two bathrooms. Amenities include a private pool, a dock, a fully equipped kitchen, a garden, and high-speed internet.
Apartment| Downtown Orlando 10 Min & Disney 25 Min - Winter Park, FL
9.7 51 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.
Pool, Hot Tub, Golf, Tennis, Fitness Center, Wifi, 1st Floor Condo - Winter Park, FL
10 4 reviews

Pool, Hot Tub, Golf, Tennis, Fitness Center, Wifi, 1st Floor Condo

apartment, Orlando
This Orlando condo, situated in the Ventura Country Club neighbourhood, is a 16km drive from Orlando International Airport and 40km from the major theme parks.
The 84 square metre self-catering apartment sleeps four guests in two bedrooms and two bathrooms, and boasts a private terrace, swimming pool, jacuzzi, sauna, and free parking, plus access to a clubhouse restaurant and further leisure facilities within the gated community.

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

Peaceful Private Gated Patio Walk To Mall Publix - Winter Park, FL
8.6 4 reviews

Peaceful Private Gated Patio Walk To Mall Publix

apartment, Altamonte Springs
This Altamonte Springs holiday home is conveniently located within 1.6km of Altamonte Mall and Cranes Roost Park, and 3.2km from Sanlando Park.
The one-bedroom, one-bathroom property sleeps four guests and features a private patio, on-site fitness centre, in-house laundry facilities, and free Wi-Fi.
Long Term Home In Beautiful Winter Park - Winter Park, FL
9.6 35 reviews

Long Term Home In Beautiful Winter Park

apartment, Winter Park
This charming three-bedroom home is located in Winter Park, a neighbourhood known for its elegant homes, just a short distance from Rollins College and a few blocks from Park Avenue. The property has received excellent ratings for its cleanliness, location and user experience.
The split-level apartment can accommodate up to six guests and is perfect for families or groups. Guests can enjoy a fully equipped kitchen, a private garden, lake access, free parking and a dedicated workspace, making this the ideal choice for a relaxing and comfortable stay.
Amazing Five-star Luxury Thornton Park Two Bedroom Apt - Close To Kia Center. - Winter Park, FL
9.8 27 reviews

Amazing Five-star Luxury Thornton Park Two Bedroom Apt - Close To Kia Center.

apartment, Orlando
This two-bedroom apartment is located in Thornton Park, Orlando, just 0.6 kilometres from Lake Eola and within 5 kilometres of attractions like Kia Center and Camping World Stadium. It has received excellent reviews from previous guests.
The apartment has one bathroom and comfortably sleeps up to four people. It comes equipped with a kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, and free parking, along with a water park, making it ideal for families.
Winter Park Pearl 6 Min Drive To Historic Park Ave - Winter Park, FL
9.9 467 reviews

Winter Park Pearl 6 Min Drive To Historic Park Ave

apartment, Casselberry
This charming cottage is located just 5 kilometres from the shops and restaurants of Park Avenue, a popular historical district in Winter Park, offering a peaceful escape from the hustle and bustle. It has received excellent ratings for its location, cleanliness, and overall user experience.
The cottage is a spacious 1000 square foot property, comfortably accommodating up to 4 guests. This home provides modern amenities including a fully equipped kitchen, three 50-inch TVs, a Jacuzzi, a private garden, and a fitness centre, along with complimentary beverages and a charcoal grill for outdoor cooking.

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

Modern Downtown Orlando Studio In A Prime Location - Winter Park, FL
No reviews

Modern Downtown Orlando Studio In A Prime Location

studio, Orlando
This studio apartment is located in Downtown Orlando, 8.5 kilometres from Church Street Station and 8.7 kilometres from the Kia Centre, with Orlando International Airport 11 kilometres away.
This 46 square metre studio accommodates up to three guests and offers a kitchenette with a microwave, air conditioning, complimentary WiFi, an on-site spa, and allows pets, with water sports and horse riding opportunities nearby.
Downtown Groovy Studio - Winter Park, FL
8.8 15 reviews

Downtown Groovy Studio

studio, Orlando
Downtown Groovy Studio offers a central Orlando location, approximately 4.6km from Church Street Station and 4.7km from the Amway Center.
This 920 square metre apartment sleeps four, features a fully equipped kitchen, free Wi-Fi, and air conditioning, and is conveniently located near Universal Studios and ICON Park.
Chic Studio Near Downtown & Theme Parks - Winter Park, FL
No reviews

Chic Studio Near Downtown & Theme Parks

studio, Orlando
This Orlando apartment is situated approximately 8.5 kilometres from Church Street Station and 8.7 kilometres from the Kia Centre, offering convenient access to downtown landmarks.
This 37 square metre studio apartment accommodates up to three guests and features a kitchenette with a microwave, complimentary WiFi, air conditioning, and a garden area, with Orlando International Airport located just 10.9 kilometres away.
Light, Bright And Full Of Delight! 2 Blocks To Park Ave - Winter Park, FL
10 1 review

Light, Bright And Full Of Delight! 2 Blocks To Park Ave

apartment, Winter Park
This two-bedroom apartment is located in Winter Park, within a 15-minute walk of the Morse Museum of American Art and Casa Feliz Historic Home Museum, and within 2 kilometres of Rollins College and the Albin Polasek Museum and Sculpture Gardens. The apartment is situated in a quiet and convenient location, perfect for exploring the city's attractions.
The self-catering apartment can accommodate up to 4 guests and has a fully equipped kitchen, a comfortable living area, a private balcony, and a shared outdoor pool. Guests can enjoy free Wi-Fi, air conditioning, and a smoke-free environment.
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