Best apartment offers in Winter Park, FL

321 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Winter Park, FL apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Serene Private Home Near The Fun - Winter Park, FL
10 42 reviews

Serene Private Home Near The Fun

apartment, Altamonte Springs
This Altamonte Springs holiday home offers a peaceful retreat, conveniently located near Wekiva Springs State Park and a short drive (exact distances unspecified) from Orlando's theme parks, including Walt Disney World Resort, Universal Orlando Resort, SeaWorld Orlando, and LEGOLAND Florida Resort.
The three-bedroom, two-bathroom property sleeps seven guests and features a fully equipped kitchen, open-plan living area, 60-inch TV, foosball table, massage chair, and workstation, ensuring comfortable accommodation for families or groups.
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.
Beautiful Downtown Condo 1/1 - Winter Park, FL
9.0 2 reviews

Beautiful Downtown Condo 1/1

apartment, Orlando
This Orlando apartment rental is situated in the South Eola district, a short walk from Lake Eola and within 3.2km of the Amway Center, Camping World Stadium, and Orlando City Stadium.
The 106 square metre flat boasts a California king-size bed, in-unit laundry, a Nespresso machine, and a terrace; it sleeps two guests and offers access to a future 9th-floor amenity space with a TV and outdoor grill.
The Ocean's Cove - Free Parking - Winter Park, FL
10 18 reviews

The Ocean's Cove - Free Parking

apartment, Orlando
This one-bedroom flat in Dover Estates, Orlando, provides excellent access to major routes, the Curry Ford West and Hourglass Districts, and is a short drive from Universal Orlando Resort and Florida Mall.
This apartment, suitable for two guests, offers air conditioning and internet, with a 11:00 AM check-out time.

Best Winter Park, FL holiday apartments with a kitchen

Modern Luxury King Suite | Central Orlando + Pool - Winter Park, FL
10 35 reviews

Modern Luxury King Suite | Central Orlando + Pool

apartment, Orlando
This modern one-bedroom apartment in Orlando, Florida, is conveniently located 8 kilometres from Universal Studios, 43 kilometres from Walt Disney World, and 27 kilometres from the new Epic Universe, with downtown Orlando attractions such as Lake Eola and the Dr. Phillips Centre just 800 metres away.
This pet-friendly accommodation for up to four guests offers resort-style amenities including a swimming pool, fitness centre, fully-equipped kitchen with stainless steel appliances, a queen-size sofa bed, a king-size bed in the master bedroom, and in-unit laundry facilities.
Cozy 1br Near Ucf 45 Min To Disney /Acogedor 1br Cerca De Ucf 45 Min De Disney - Winter Park, FL
9.6 4 reviews

Cozy 1br Near Ucf 45 Min To Disney /Acogedor 1br Cerca De Ucf 45 Min De Disney

apartment, Union Park
This one-bedroom flat is located in a quiet Orlando neighbourhood, offering easy access to major theme parks, a water park, and attractions such as the Rollins Museum of Art and Winter Park History Museum, all within 8 kilometres.
This accommodation for four guests includes a king-size bed, air conditioning, and a kitchen equipped with a fridge, microwave, and dishwasher, with garden and parking facilities available.
Luxurious 2br Near Park Ave & Rollins College - Winter Park, FL
10 31 reviews

Luxurious 2br Near Park Ave & Rollins College

apartment, Goldenrod
This two-bedroom flat is located in a quiet residential district of Goldenrod, just 500 meters from Park Avenue's shops and restaurants, and a short drive from Rollins College and Full Sail University.
The property accommodates up to six guests and offers a fully equipped kitchen, air conditioning, a garden, private parking for four cars, and a dedicated workspace with Wi-Fi, ideal for those seeking a convenient stay.
Premier Resort Condos Near Disney & Universal - Winter Park, FL
9.3 3438 reviews

Premier Resort Condos Near Disney & Universal

studio, Orlando
This studio apartment is located just over 1.6 kilometres from Universal Studios Orlando and ICON Park, placing you within easy reach of the excitement and attractions of Orlando. It has received excellent ratings for location, cleanliness and user experience, ensuring a comfortable and enjoyable stay.
The studio features a bedroom, bathroom, and kitchen with a fridge, freezer, microwave oven, and dishwasher. You can also enjoy a range of facilities including a swimming pool, Jacuzzi, terrace, garden, spa, bar, fitness centre, tennis court, and parking.

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

Enjoy Your Stay In Our Cozy 2 Bedroom 1 Bath Guest Suite.newly Renovated Space - Winter Park, FL
10 1 review

Enjoy Your Stay In Our Cozy 2 Bedroom 1 Bath Guest Suite.newly Renovated Space

apartment, Altamonte Springs
This Altamonte Springs flat is ideally situated, offering a 16-kilometre drive to downtown Orlando, a 32-kilometre journey to Orlando's theme parks, and a 56-kilometre route to the East Coast beaches, with Winter Park's dining and shopping readily accessible.
This two-bedroom flat accommodates up to four guests and features air conditioning, a swimming pool, a jacuzzi, and parking, with a kitchen equipped with a fridge, microwave oven, and dishwasher, and is located near Wekiwa Springs State Park and Rock Springs Run.
Grace Haven - Winter Park, FL
10 6 reviews

Grace Haven

apartment, Orlando
This Orlando flat is located in a private, tranquil district, offering a peaceful retreat for guests.
This one-bedroom, one-bathroom flat accommodates two people and features a full kitchen, air conditioning, and parking, with internet access and pets allowed.
Tranquil Oasis: 4br Pool Home - Winter Park, FL
9.4 56 reviews

Tranquil Oasis: 4br Pool Home

apartment, Goldenrod
This Winter Park house, situated in a quiet neighbourhood a short drive (approximately 16km) from Park Avenue, Rollins College, and the University of Central Florida, offers convenient access to local attractions.
The four-bedroom, two-bathroom property sleeps eight guests and boasts a private fenced backyard with a swimming pool and hot tub, a fully equipped kitchen, and two parking spaces; nearby amenities include the Winter Park Farmers' Market and restaurants such as The Ravenous Pig and Prato.
Spacious Private & Lovely - Winter Park, FL
No reviews

Spacious Private & Lovely

apartment, Winter Park
This one-bedroom flat is located adjacent to Interlachen Country Club in Winter Park, offering a 5-minute walk to Lake Howell Plaza and a 5-minute drive to Park Avenue's shops and restaurants.
This accommodation for four guests provides internet, air conditioning, a kitchen, and parking, with Universal Orlando Resort 25-35 kilometres and Walt Disney World 35-45 kilometres away.

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

The Gojjo Retreat Walkable Backyard Guesthouse - Winter Park, FL
10 3 reviews

The Gojjo Retreat Walkable Backyard Guesthouse

apartment, Orlando
This newly constructed luxury tiny home, ideal for couples or solo travellers, is located in downtown Orlando, offering convenient access to premier dining and entertainment venues, with the Kia Centre and Camping World Stadium within 2 kilometres.
This one-bedroom, one-bathroom flat accommodates up to four guests and features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a terrace/balcony, parking, and an on-site fire pit area, with the option for a private chef experience.
Charming 3-bedroom Near Orlando Theme Parks, Downtown And Golf Courses - Winter Park, FL
9.8 20 reviews

Charming 3-bedroom Near Orlando Theme Parks, Downtown And Golf Courses

apartment, Casselberry
This recently renovated three-bedroom, two-bathroom flat in Casselberry, Seminole County, offers convenient access to Orlando's theme parks (40 kilometres), downtown Orlando (32 kilometres), Wekiva Springs State Park (32 kilometres), and coastal destinations including Coco Beach and NASA (64 kilometres).
This 172-square-meter accommodation, suitable for up to six guests, includes a fully equipped kitchen with a microwave and dishwasher, air conditioning, Wi-Fi, a washer/dryer, and private parking, with local shopping and entertainment venues within walking distance.
King Bed Smoking - Winter Park, FL
9.8 27 reviews

King Bed Smoking

apartment, Sky Lake
This Orlando flat is located in Sky Lake, 9 kilometres from Orlando International Airport, 3 kilometres from Florida Mall, and 7 kilometres from Holy Land Experience, with convenient access to Universal Studios and SeaWorld.
This 14 square metre studio apartment accommodates two guests and features air conditioning, complimentary WiFi, free private parking, a king-size bed, a private bathroom, a work desk, a television, a refrigerator, and a microwave.
Lake House - Winter Park, FL
9.8 209 reviews

Lake House

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.
©2026 cozycozy.com