Best apartment offers in Winter Park, FL

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Winter Park, FL apartments
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231 Best apartments in Winter Park, FL

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

Among the 231 accommodations in Winter Park, FL, here are the 4 best family friendly holiday apartments

Historic Orlando Casita Joy, Dt, Lake Eola, Delaney Park, 2 Bedrooms 1 Bathroom Unit B - Winter Park, FL
8.7 10 reviews
Winter Park, FL
28/06 – 01/07
₹19144/nighttotal: ₹57432 (3 )

Historic Orlando Casita Joy, Dt, Lake Eola, Delaney Park, 2 Bedrooms 1 Bathroom Unit B

2 4
apartment , Orlando
This renovated Casita, located in downtown Orlando near Lake Eola and Delaney Park, is a 12-minute walk from Church Street Station and within 1.3 km of the Amway Center and 4 km of Camping World Stadium.
This 2-bedroom, 1-bathroom apartment offers 300 square metres of space, sleeps up to 7 guests, and includes free Wi-Fi, private parking, a fully equipped kitchen, and air conditioning.
The Gojjo Retreat - Private Home Walkable Retreat - Winter Park, FL
9.9 16 reviews
Winter Park, FL
14/08 – 21/08
₹13719/nighttotal: ₹96033 (7 )

The Gojjo Retreat - Private Home Walkable Retreat

1 2
apartment , Orlando
This brand new 2025 luxury tiny home in Orlando offers a tranquil urban oasis, located within 500 meters of top dining establishments and close to the city's attractions.
This one-bedroom, one-bathroom flat accommodates up to four guests, featuring air conditioning, Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, plus off-street parking and a communal fire pit area.
Spacious Home With Pool & Hot Tub Near Downtown - Winter Park, FL
9.9 163 reviews
Winter Park, FL
14/08 – 21/08
₹41783/nighttotal: ₹292481 (7 )

Spacious Home With Pool & Hot Tub Near Downtown

3 2
apartment , Orlando
This Orlando apartment is conveniently located near Downtown Orlando, just 5 kilometres from restaurants, bars, and shops, and within a 30-minute drive of Universal Studios, Walt Disney World, and SeaWorld Orlando. The apartment has received excellent ratings for its cleanliness, location, and user experience.
The property offers three bedrooms and two bathrooms, accommodating up to six guests. This family-friendly apartment provides a range of amenities including a private entrance, parking, a swimming pool, a jacuzzi, a garden, a fitness centre, and a kitchen with a fridge, freezer, microwave, and dishwasher.
Yania's Cozy Getaway - Winter Park, FL
9.8 16 reviews
Winter Park, FL
28/06 – 18/07
₹9087/nighttotal: ₹181740 (20 )

Yania's Cozy Getaway

1 1
apartment , Azalea Park
This Azalea Park self-contained flat is conveniently located minutes from Waterford Lakes Town Centre and major highways, offering easy access to Orlando's theme parks.
The one-bedroom, one-bathroom apartment sleeps two guests and features a private patio, kitchenette with fridge and microwave, air conditioning, internet access, parking, and allows pets; nearby activities include fishing and exploring the area's attractions such as Florida Mall and Orlando International Premium Outlets.

Best Winter Park, FL holiday apartments with a kitchen

Fun Spacious Pool Home W/ Outdoor Kitchen & Games - Winter Park, FL
9.8 29 reviews
Winter Park, FL
28/06 – 01/07
₹30497/nighttotal: ₹91491 (3 )

Fun Spacious Pool Home W/ Outdoor Kitchen & Games

1 4
apartment , Winter Park
This Lake Baldwin house, a short distance (1.6km) from Baldwin Park and a 7-minute drive from Winter Park, offers easy access to local amenities and attractions.
Sleeping nine guests, this four-bedroom, two-bathroom property boasts a private pool, spacious living areas with a pool table and large-screen TVs, and is close to a 5km jogging path and a dog park.
Thornton Park Oasis 1 Bedroom - Winter Park, FL
10 22 reviews
Winter Park, FL
28/06 – 18/07
₹11246/nighttotal: ₹224920 (20 )

Thornton Park Oasis 1 Bedroom

1 1
apartment , Orlando
This Orlando apartment is centrally located in downtown Orlando, within walking distance of Lake Eola Park, the Amway Center, and the Dr. Philips Center for the Performing Arts.
The 70 square metre (753 square feet) self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes amenities such as Wi-Fi, air conditioning, a garden, and parking; nearby attractions include the Florida Mall and Orlando International Premium Outlets.
Charming Bungalow In Winter Park - Winter Park, FL
9.9 75 reviews
Winter Park, FL
10/07 – 18/07
₹23328/nighttotal: ₹186624 (8 )

Charming Bungalow In Winter Park

3 4
apartment , Orlando
This Orwin Manor bungalow offers three bedrooms and two bathrooms, comfortably sleeping six guests, and is conveniently located near Orlando's hospitals and downtown, providing easy access to local restaurants.
The 160 square metre single-family home boasts an open-plan layout, hardwood floors, a fully equipped kitchen including a dishwasher, air conditioning, ample parking, and a landscaped yard; emotional support animals are permitted for an additional fee.
Heart Of Orlando! Cozy Home Near Baldwin Park - Winter Park, FL
9.1 75 reviews
Winter Park, FL
10/07 – 18/07
₹10107/nighttotal: ₹80856 (8 )

Heart Of Orlando! Cozy Home Near Baldwin Park

1 4
apartment , Orlando
This Orlando flat is peacefully situated near Baldwin Park, a short 16km drive from Downtown Orlando and Winter Park, and within 56km of Disney World and Universal Studios.
The self-catering apartment, sleeping four, boasts a garden, free on-site parking, Wi-Fi, and is conveniently located near the Cady Way Trail, offering easy access to public transport.

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.

Destinations nearby

Best Winter Park, FL holiday apartments with air conditioning

Maria's Orlando Vacation Home - Winter Park, FL
9.4 149 reviews
Winter Park, FL
28/06 – 01/07
₹12471/nighttotal: ₹37413 (3 )

Maria's Orlando Vacation Home

1 4
apartment , Azalea Park
This three-bedroom, two-bathroom house in Azalea Park, Orlando, offers convenient access to Downtown Orlando (16km), shopping malls (32km), and theme parks (48km).
Sleeping six guests, this property includes a kitchen with fridge, freezer, and microwave, air conditioning, parking, and excellent user and location ratings; enjoy nearby restaurants and easy access to major roadways.
Near Dwtn + Sleeps 6 + Patio - Winter Park, FL
9.5 51 reviews
Winter Park, FL
28/06 – 01/07
₹17842/nighttotal: ₹53526 (3 )

Near Dwtn + Sleeps 6 + Patio

1 4
apartment , Orlando
This two-bedroom Orlando apartment is conveniently located in downtown Orlando, approximately 8km from the city centre, 32km from Universal Studios Florida, and 40km from Walt Disney World.
The 2-bedroom flat sleeps six guests and features a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus a garden, free on-site parking, smart TV, high-speed Wi-Fi, and central air conditioning.
Spacious Private & Lovely - Winter Park, FL
9.4 29 reviews
Winter Park, FL
28/06 – 18/07
₹7328/nighttotal: ₹146560 (20 )

Spacious Private & Lovely

1 1
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.
Suites By The Wellborn - Winter Park, FL
8.5 85 reviews
Winter Park, FL
28/06 – 01/07
₹10481/nighttotal: ₹31443 (3 )

Suites By The Wellborn

1 4
studio , Orlando
This studio apartment is centrally located in Orlando, a 14-minute walk from Church Street Station and 1.4 kilometres from the Kia Centre.
Guests can enjoy complimentary Wi-Fi, air conditioning, a private bathroom with a walk-in shower, and an on-site restaurant serving dinner and cocktails, with an outdoor fireplace area available for relaxation.

Best pet-friendly Winter Park, FL holiday apartments

Among the 231 accommodations in Winter Park, FL, here are the 4 best pet friendly holiday apartments

High-end Downtown Orlando Penthouse With Patio - Winter Park, FL
10 1 review
Winter Park, FL
28/06 – 18/07
₹38684/nighttotal: ₹773680 (20 )

High-end Downtown Orlando Penthouse With Patio

2 1
apartment , Orlando
This luxury flat is located in the South Eola district of Downtown Orlando, offering convenient access to the Kia Centre (approximately 1.6 kilometres away) and Universal Orlando Resort (approximately 12.8 kilometres away).
This modern penthouse provides accommodation for up to four guests with two king-sized bedrooms, two bathrooms, air conditioning, and Wi-Fi, with parking available and pets permitted.
Cozy College Park Duplex @Lake Fairview. Sleeps7 - Winter Park, FL
9.3 148 reviews
Winter Park, FL
10/07 – 18/07
₹12565/nighttotal: ₹100520 (8 )

Cozy College Park Duplex @Lake Fairview. Sleeps7

1 4
apartment , Orlando
This three-bedroom apartment is situated in College Park, a district just 8km from Orlando city centre, with easy access to attractions like Lake Eola Park and the theme parks.
The 1150 sq ft property features a fully equipped kitchen, a comfortable living room with a 55” TV, and a dedicated workspace in one of the bedrooms, making it ideal for families or groups of up to seven guests.
Luxurious Penthouse With Large Patio - Winter Park, FL
Winter Park, FL
28/06 – 18/07
₹42163/nighttotal: ₹843260 (20 )

Luxurious Penthouse With Large Patio

2 1
apartment , Orlando
This Orlando flat offers prime downtown access, situated a 13-minute walk from Church Street Station, a 17-minute walk from the Kia Centre, and 3.7 kilometres from Camping World Stadium.
This spacious two-bedroom, two-bathroom apartment, covering 175 square metres and accommodating up to seven guests, features a fully equipped kitchen, a large patio, sun terrace, fitness centre, barbecue facilities, and complimentary private parking with an electric vehicle charging station.
2 Bdrm Penthouse With Billiards - Winter Park, FL
9.9 9 reviews
Winter Park, FL
28/06 – 18/07
₹29220/nighttotal: ₹584400 (20 )

2 Bdrm Penthouse With Billiards

1 1
apartment , Orlando
This Orlando penthouse apartment is situated in the city centre, less than 0.6km from various attractions and 14km from Orlando International Airport.
The 150 square metre dwelling boasts two bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, a billiards table, free Wi-Fi, and accommodates up to seven guests.
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