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

Stylish Boutique Guest House In Winter Park - Winter Park, FL
10 109 reviews
Winter Park, FL
28/06 – 18/07
₹16787/nighttotal: ₹335740 (20 )

Stylish Boutique Guest House In Winter Park

3 1
apartment , Winter Park
This two-bedroom flat is ideally located in Winter Park, just a short distance from attractions like the Casa Feliz Historic Home Museum and the Morse Museum of American Art. It has received excellent reviews from previous guests.
The apartment comfortably sleeps four guests and features a fully equipped kitchen, a fireplace, and a balcony. Guests can enjoy the on-site fitness centre, swimming pool, and garden, as well as free Wi-Fi and parking.
Lake Marion Apt W/ Canoe In Altamonte Springs! - Winter Park, FL
9.8 188 reviews
Winter Park, FL
23/06 – 28/06
₹14114/nighttotal: ₹70570 (5 )

Lake Marion Apt W/ Canoe In Altamonte Springs!

1 2
apartment , Altamonte Springs
This charming one-bedroom house is situated in Altamonte Springs, just 18 kilometres from downtown Orlando and Church Street Station, offering a peaceful escape from the city's hustle and bustle. The property has consistently received excellent ratings for its cleanliness, location and overall experience.
The 42 square metre house comfortably accommodates two guests and features a separate bedroom and living area. Guests can enjoy a fully equipped kitchen, a private garden, a spa, free Wi-Fi, air conditioning, and direct access to Lake Marion, complete with a canoe for exploring the tranquil waters.
Clear Lake Retreat: Private Pool And Spa, Lakefront - Winter Park, FL
10 2 reviews
Winter Park, FL
23/06 – 28/06
₹67538/nighttotal: ₹337690 (5 )

Clear Lake Retreat: Private Pool And Spa, Lakefront

4 2
apartment , Orlando
This lakefront dwelling is situated in Orlando, just 6 kilometres from Downtown Orlando and 9 kilometres from International Drive, making it convenient for exploring the city's attractions.
The spacious property offers 4 bedrooms and 3 bathrooms, accommodating up to 10 guests comfortably. Relax by the private pool, enjoy the sunset views from the terrace, or take advantage of the amenities like the Jacuzzi, garden, and laundry facilities.
3 Bedroom Corner Suite - Winter Park, FL
8.0 1 review
Winter Park, FL
28/06 – 18/07
₹37492/nighttotal: ₹749840 (20 )

3 Bedroom Corner Suite

3 1
apartment , Orlando
This Orlando apartment is situated in the South Eola district, a short walk from Lake Eola and within 2km of Church Street Station.
The 186 square metre property offers three bedrooms, two bathrooms, sleeps six, and includes a balcony, free Wi-Fi, covered parking, and is close to Universal Orlando Resort and other attractions.

Best Winter Park, FL holiday apartments with a kitchen

Modern Winter Park 2br Near Park Ave Sleeps 6 - Winter Park, FL
10 21 reviews
Winter Park, FL
28/06 – 01/07
₹21594/nighttotal: ₹64782 (3 )

Modern Winter Park 2br Near Park Ave Sleeps 6

1 4
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.
Updated Home* 2 King Bed Suites * Downtown Orlando - Winter Park, FL
9.8 138 reviews
Winter Park, FL
10/07 – 18/07
₹22468/nighttotal: ₹179744 (8 )

Updated Home* 2 King Bed Suites * Downtown Orlando

1 4
apartment , Orlando
This charming two-bedroom apartment in Downtown Orlando is just a short distance from the Amway Center and Dr. Phillips Performing Arts Center, with Universal Studios and Disney World reachable within 30 minutes. With excellent ratings for cleanliness, location and user experience, this property offers a comfortable and convenient base for exploring the city.
This spacious home sleeps up to six guests and features a well-equipped kitchen, a private garden and parking. Enjoy the convenience of being close to restaurants, bars and shops, as well as the option of preparing meals in the apartment.
The Lake House - Winter Park, FL
9.8 213 reviews
Winter Park, FL
28/07 – 01/08
₹9689/nighttotal: ₹38756 (4 )

The Lake House

1 2
apartment , Winter Park
This Winter Park flat, a 1-bedroom apartment sleeping four, is situated in a quiet residential area, a 6.4km drive from Park Avenue's upscale shops and restaurants and within walking distance of Starbucks, Panera Bread, Publix, Walgreens, and Sprouts.
The 35-square-metre self-catering property features original terrazzo floors, a fully equipped kitchen with cooking basics, a luxury bathroom with C.O. Bigelow products, a Roku TV, Wi-Fi, and a welcome basket; it also boasts a private entrance and secluded lake views.
10 Min To Winter Park, Games, Gym, King Bd, Coffee - Winter Park, FL
9.9 61 reviews
Winter Park, FL
10/07 – 18/07
₹19927/nighttotal: ₹159416 (8 )

10 Min To Winter Park, Games, Gym, King Bd, Coffee

1 4
apartment , Casselberry
This Casselberry apartment, less than 48km from Walt Disney World and Universal Studios and 13km from Winter Park, offers easy access to major Orlando attractions.
The three-bedroom, two-bathroom property sleeps nine, boasting a chef's kitchen, dedicated home gym, children's play area with trampoline and slide, and amenities including fast Wi-Fi and a smart TV.

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

The Emerald, Milk District Gem! Unit 2 - Winter Park, FL
9.7 28 reviews
Winter Park, FL
28/06 – 18/07
₹11159/nighttotal: ₹223180 (20 )

The Emerald, Milk District Gem! Unit 2

1 1
apartment , Orlando
This Milk District Airbnb in Orlando, Florida is conveniently located approximately 1.6km from Lake Eola and a short drive from Downtown Orlando, offering easy access to major attractions such as Universal Studios (25-minute drive) and Walt Disney World Resort (30-40 minute drive).
The self-catering property features one bedroom, one bathroom, and sleeps three guests; amenities include a kitchen with fridge, freezer and microwave, air conditioning, a garden, parking, and excellent guest reviews, alongside pet-friendly and 4/20-friendly policies (outdoors only).
Cute & Cozy Guest Suite In Orlando Near Disney, Universal, Downtown, And Airport - Winter Park, FL
Winter Park, FL
28/06 – 18/07
₹8143/nighttotal: ₹162860 (20 )

Cute & Cozy Guest Suite In Orlando Near Disney, Universal, Downtown, And Airport

1 1
apartment , Conway
This private studio apartment in Conway is situated near the Sodo and Hourglass Districts, offering convenient access to Orlando International Airport (24 km), Disney (40 km), Universal Studios (32 km), and Downtown Orlando (24 km).
This soundproofed suite accommodates up to four guests and features air conditioning, internet, and parking, making it an ideal base for exploring nearby attractions such as Universal Orlando Resort and Florida Mall.
Cozy Town Suites B - Winter Park, FL
9.6 47 reviews
Winter Park, FL
23/06 – 28/06
₹8211/nighttotal: ₹41055 (5 )

Cozy Town Suites B

1 2
apartment , Eatonville
This one-bedroom apartment is situated in Winter Park, a historic town just 1.6 kilometres from Eatonville, offering easy access to the Interstate 4 and a 42-kilometre drive to Walt Disney World Resort.
The self-contained apartment, ideal for two guests, is newly renovated and features a queen-size bed, a shower, a fully equipped kitchen, air conditioning, parking, and complimentary Wi-Fi.
Close To The Action, Peaceful When You Return  -  2br In Downtown, Sleeps 6 - Winter Park, FL
10 5 reviews
Winter Park, FL
28/06 – 01/07
₹23112/nighttotal: ₹69336 (3 )

Close To The Action, Peaceful When You Return - 2br In Downtown, Sleeps 6

2 4
apartment , Orlando
This Lawsona - Fern Creek flat is located in Downtown Orlando, under 500 metres from Lake Eola Park and within a 10-minute drive of the Amway Centre and Camping World Stadium.
This two-bedroom flat accommodates six guests and offers a fully equipped kitchen with a microwave oven and dishwasher, air conditioning, parking, and an on-site washer and dryer, with self-check-in available via a smart lock.

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

Luxury King Suite Heart Orlando: Pool & Gym Access - Winter Park, FL
9.4 20 reviews
Winter Park, FL
23/06 – 28/06
₹19335/nighttotal: ₹96675 (5 )

Luxury King Suite Heart Orlando: Pool & Gym Access

1 2
apartment , Orlando
This modern one-bedroom loft apartment in Orlando, Florida, offers a convenient base, situated 800 metres from Lake Eola and downtown attractions, and 2.4 to 4.8 kilometres from Universal Studios and Walt Disney World Resort.
This pet-friendly accommodation for up to four guests boasts a fully-equipped kitchen, in-unit laundry, air conditioning, and access to resort amenities including a swimming pool, fitness centre, and parking.
Tranquil Hideaway: 2-bedroom Retreat Near Mills/50 - Winter Park, FL
9.4 3 reviews
Winter Park, FL
23/06 – 28/06
₹13411/nighttotal: ₹67055 (5 )

Tranquil Hideaway: 2-bedroom Retreat Near Mills/50

2 2
apartment , Orlando
This three-bedroom Colonialtown North apartment in Orlando, Florida, is situated 1.1 kilometres from Harry P. Leu Gardens and within a 3-5 kilometre radius of the Plaza Theatre and Orlando Museum of Art.
The 3-bedroom property sleeps five guests and features a fully equipped kitchen, free Wi-Fi, a garden, and parking; nearby attractions include the Kia Centre and on-site barbecue facilities.
1bd Apt In Downtown W/ King Bed |Office, Free Prkg - Winter Park, FL
9.6 119 reviews
Winter Park, FL
28/06 – 18/07
₹8076/nighttotal: ₹161520 (20 )

1bd Apt In Downtown W/ King Bed |Office, Free Prkg

1 1
apartment , Orlando
This downtown Orlando flat is situated three blocks from the city's busiest streets, within walking distance of Lake Eola Park and a short drive (approximately 32km) from Walt Disney World Resort and Universal Orlando Resort.
The self-catering apartment offers a king-size bed, dedicated workspace, fully equipped kitchen, on-site laundry, private parking, and accommodates two guests, with keyless access and excellent guest reviews.
Cozy Blue Bungalow - Winter Park, FL
9.7 55 reviews
Winter Park, FL
28/06 – 18/07
₹11732/nighttotal: ₹234640 (20 )

Cozy Blue Bungalow

1 1
apartment , Altamonte Springs
This one-bedroom Altamonte Springs apartment, conveniently located near shopping and a short drive (approx. 24km) from Orlando city centre, offers easy access to major airports and theme parks.
The self-catering flat sleeps two guests and features a kitchen with freezer and microwave, air conditioning, a garden, parking, and excellent guest reviews; enjoy a tranquil setting with outdoor seating and proximity to grocery stores and the Altamonte Mall.
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