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

Walk Into Tropical Paradise - Pool - Gym - Hot Tub - Winter Park, FL
9.4 27 reviews

Walk Into Tropical Paradise - Pool - Gym - Hot Tub

apartment, Altamonte Springs
This Altamonte Springs holiday home, conveniently located near Interstate 4, offers easy access to Orlando's theme parks and is within a short distance of Altamonte Springs' shopping and dining areas.
Sleeping up to nine guests, this four-bedroom, two-bathroom property boasts a private backyard with a pool, hot tub, mini-golf, and yard games, plus a fully equipped kitchen, home gym, and multiple large-screen TVs.
Remodeled Downtown Orlando Oasis! Remodeled Home! Close To Disney, Universal! - Winter Park, FL
10 1 review

Remodeled Downtown Orlando Oasis! Remodeled Home! Close To Disney, Universal!

apartment, Orlando
This Orlando holiday home is conveniently located within 5km of the Plaza Theatre, Orlando Fashion Square, and Orlando Regional Medical Centre.
The two-bedroom, two-bathroom property sleeps five guests and boasts a private patio, swimming pool, spa, fitness centre, and BBQ facilities, all within a smoke-free environment.
Stay Near Winter Park Action At Our 2-bedroom Apartment - Winter Park, FL
10 2 reviews

Stay Near Winter Park Action At Our 2-bedroom Apartment

apartment, Winter Park
This two-bedroom flat is located in Hannibal Square, Winter Park, approximately 8.5 kilometres from Universal Orlando Resort and 6.7 kilometres from Orlando International Premium Outlets.
This 88 square metre apartment accommodates up to four guests and features a fully equipped kitchen, air conditioning, free WiFi, an outdoor swimming pool, and a garden with a grill.
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.

Best Winter Park, FL holiday apartments with a kitchen

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.
Uptown Orlando Mid Century - Near Medical District - Winter Park, FL
9.9 33 reviews

Uptown Orlando Mid Century - Near Medical District

apartment, Orlando
This Orlando duplex, ideally located minutes (approximately 5km) from AdventHealth and Orlando Health hospitals, offers easy access to central Orlando attractions.
The one-bedroom, one-bathroom apartment sleeps three, features a fully equipped kitchen, smart TV, Alexa, in-unit laundry, a private garden, and two off-street parking spaces.
6 Mi To Downtown Orlando: Quiet Home W/ Sunroom - Winter Park, FL
9.3 6 reviews

6 Mi To Downtown Orlando: Quiet Home W/ Sunroom

apartment, Winter Park
This Winter Park holiday apartment is ideally located within walking distance of Winter Park Village and Park Avenue, and a 9.6km drive from downtown Orlando, offering easy access to Disney World and Universal Studios.
The two-bedroom, one-bathroom property sleeps four guests and features a well-equipped kitchen, in-home laundry, a private unfenced backyard, and a sunroom; pets are welcome (maximum two, fee applies).
The Centralized Haven 3 Bedroom Home Restaurants, Attractions & Fun Minutes Away - Winter Park, FL
9.0 8 reviews

The Centralized Haven 3 Bedroom Home Restaurants, Attractions & Fun Minutes Away

apartment, Altamonte Springs
This three-bedroom apartment in Altamonte Springs is conveniently located 8 kilometres from the Trophy Club of Orlando and 10 kilometres from the Mall at Millenia, offering easy access to both leisure and shopping.
The 214 square metre property features three bathrooms, a living room with a futon, and a kitchen equipped with a microwave oven and dishwasher, comfortably accommodating up to seven guests.

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

The Pineapple Express - Winter Park, FL
8.8 4 reviews

The Pineapple Express

apartment, Orlando
This Orlando flat is located approximately 5 kilometres from the Kia Centre and Church Street Station, and 6.9 kilometres from Camping World Stadium.
This 111 square metre flat offers accommodation for up to 9 guests, featuring a fully equipped kitchen, complimentary WiFi, and on-site parking, with a check-out time of 10:00 AM.
King Bed | Grill | Pets | Central Location! - Winter Park, FL
9.6 370 reviews

King Bed | Grill | Pets | Central Location!

apartment, Azalea Park
This four-bedroom home is located in Azalea Park, just 15 minutes from Orlando/Winter Park and the airport, and 30 minutes from Disney and Universal. The property has received excellent ratings for location, cleanliness, and overall user experience.
This spacious house spans 186 square metres, offering ample room for a large family or group of friends. Guests can enjoy a private pool, a fully equipped kitchen, a large garden, and secure parking for up to six vehicles.
Cozy Orlando Home Close To Parks, Dining, And Downtown Fun - Winter Park, FL
10 2 reviews

Cozy Orlando Home Close To Parks, Dining, And Downtown Fun

apartment, Orlando
This Orlando apartment, situated in the Lawsona-Fern Creek neighbourhood, is a 13-minute walk (approximately 1km) from Lake Eola Park and offers easy access to attractions such as the Florida Mall and Universal Orlando Resort.
The two-bedroom, one-bathroom property sleeps six guests and features a fully equipped kitchen with dishwasher, a terrace, air conditioning, Wi-Fi, and a workspace, perfect for families or groups visiting the city.
Stylish Retreat Near Park Ave & Rollins College - Winter Park, FL
10 34 reviews

Stylish Retreat Near Park Ave & Rollins College

apartment, Goldenrod
This Winter Park maisonette in Goldenrod offers a stylish, light-filled duplex with a modern open-concept layout, featuring two bedrooms and two bathrooms for up to four guests.
The property includes a fully equipped kitchen, in-unit washer and dryer, a private fenced garden, and parking, with a strict no-smoking policy to ensure a fresh environment for visitors exploring the local attractions.

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

Floyd - Luxury 2br W/ Rooftop Pool, Gym, Balcony - Winter Park, FL
10 1 review

Floyd - Luxury 2br W/ Rooftop Pool, Gym, Balcony

apartment, Orlando
This modern luxury condominium in Orlando offers excellent city views and is centrally located, placing you within a 1.6 to 2.4 kilometre drive of the Amway Centre, Downtown Orlando, International Drive, and the Orlando Convention Centre, with Disneyworld and Universal Studios also within easy reach. This two-bedroom, two-bathroom flat accommodates up to five guests and features a fully equipped kitchen, high-speed Wi-Fi, air conditioning, and access to building amenities such as a rooftop swimming pool and fitness centre, with pets permitted.
Renovated College Park 3/2 Sleeps10 Close To Wp - Winter Park, FL
9.3 215 reviews

Renovated College Park 3/2 Sleeps10 Close To Wp

house, Orlando
This newly renovated three-bedroom duplex, sleeping up to ten guests, is situated in north College Park, bordering Lake Fairview, approximately 13km from downtown Orlando and 32km from the theme parks.
The 111m² property boasts a fully equipped kitchen with dishwasher, multiple Roku TVs, a private fenced backyard, and step-free porch access; nearby attractions include College Park's restaurants and historic neighbourhoods.
Orlando Cp Duplex. Pet Friendly. Near Dt & Wp ️ - Winter Park, FL
No reviews

Orlando Cp Duplex. Pet Friendly. Near Dt & Wp ️

apartment, Orlando
This College Park flat offers a 7-minute drive to downtown Orlando's nightlife and arts scene, with Universal Studios 17 minutes away and Walt Disney World 26 minutes distant.
This two-bedroom duplex accommodates up to seven guests and features a private, fenced garden suitable for one pet under 11kg, plus private parking for two to three vehicles under a carport.
Greatest Location In Winter Park! (4) - Winter Park, FL
9.5 69 reviews

Greatest Location In Winter Park! (4)

apartment, Winter Park
This Winter Park house enjoys an exceptional location, practically on the Rollins College campus and just 0.16 kilometres from Park Avenue's shops and restaurants, offering easy access to the Winter Park Saturday Farmers Market.
The two-bedroom, two-bathroom property sleeps six guests, features a fully equipped kitchen with dishwasher, air conditioning, a jacuzzi, and a garden; multiple similar units are available for larger groups.
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