Best apartment offers in Winter Park, FL

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Winter Park, FL apartments
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231 Holiday apartments in Winter Park, FL

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

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

Delaney House W Private Backyard - Winter Park, FL
9.0 2 reviews
Winter Park, FL
28/07 – 01/08
NZ$294/nighttotal: NZ$1176 (4 )

Delaney House W Private Backyard

1 2
apartment , Orlando
This Delaney Park holiday home is situated within 2km of Orlando Regional Medical Center and the Dr. Phillips Center for the Performing Arts, and within 5km of Camping World Stadium and the Kia Center.
The one-bedroom, one-bathroom property sleeps three guests and features a fully equipped kitchen, Smart TV, washing machine, and access to a spa; nearby attractions include Church Street Station and Orlando Station, both within a 20-30 minute walk.
Yania's Cozy Getaway - Winter Park, FL
9.8 16 reviews
Winter Park, FL
28/06 – 18/07
NZ$169/nighttotal: NZ$3380 (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.
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking. - Winter Park, FL
9.2 18 reviews
Winter Park, FL
23/06 – 28/06
NZ$554/nighttotal: NZ$2770 (5 )

Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.

3 2
apartment , Orlando
This Holden-Paramore holiday home is situated in Orlando, a 15-minute walk (approximately 1.2km) from the Dr Phillips Center for the Performing Arts and the Kia Center, and under 3.2km from Camping World Stadium.
This three-bedroom, one-bathroom property sleeps four guests and offers a fully equipped kitchen, in-house laundry, smart TV, free parking, and Wi-Fi; board games are provided for leisure.
Lakefront Luxury Pool 3100sq Ft On Lake. - Winter Park, FL
9.9 85 reviews
Winter Park, FL
28/07 – 01/08
NZ$1151/nighttotal: NZ$4604 (4 )

Lakefront Luxury Pool 3100sq Ft On Lake.

1 2
apartment , Orlando
This luxurious five-bedroom villa is located near Lake Barton in central Florida, offering convenient access to Orlando's theme parks, though precise distances aren't specified.
Sleeping up to 14 guests, this exceptional property boasts a private heated pool, hot tub, lakefront access with a boat ramp, a full-size volleyball court, and an outdoor kitchen, alongside high-end amenities including bidets in every bathroom.

Best Winter Park, FL holiday apartments with a kitchen

Near Dwtn + Sleeps 6 + Patio - Winter Park, FL
9.5 51 reviews
Winter Park, FL
28/06 – 01/07
NZ$321/nighttotal: NZ$963 (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.
Suites By The Wellborn - Winter Park, FL
8.8 74 reviews
Winter Park, FL
28/07 – 01/08
NZ$175/nighttotal: NZ$700 (4 )

Suites By The Wellborn

1 2
apartment , Orlando
Apartment with an excellent rating of 88% based on 74 reviews. You will be based in Orlando.
Facilities and services: a bar, a kitchen and a restaurant. This apartment is ideal for families.
10 Min To Winter Park, Games, Gym, King Bd, Coffee - Winter Park, FL
9.9 61 reviews
Winter Park, FL
10/07 – 18/07
NZ$359/nighttotal: NZ$2872 (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.
Milk District Hideaway - Winter Park, FL
10 3 reviews
Winter Park, FL
28/06 – 01/07
NZ$213/nighttotal: NZ$639 (3 )

Milk District Hideaway

2 4
apartment , Orlando
This flat is located in Orlando's Milk District, a short drive from downtown and its entertainment options.
This residence accommodates up to six guests and features a fully equipped kitchen, air conditioning, and fast Wi-Fi.

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 two-day stay, you'd want to see the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass anywhere. Then, head over to the scenic Rollins College campus, known for its beautiful architecture and lush gardens. You can also take a stroll along Park Avenue, Winter Park's main street, with its charming shops and restaurants.
  • What are the best apartments in Winter Park, FL?

    Among the apartments in Winter Park, FL, Modern Tropical Pool Home , Downtown (Ivanhoe Village) Loft Apartment and Upscale Loft Space Close To Downtown are the most popular ones.

  • Which neighborhoods in Winter Park, FL are best for renting an apartment?

    The best neighbourhoods for renting an apartment are generally considered to be the areas around Park Avenue, with its vibrant atmosphere and easy access to shops and restaurants, or the more residential areas of Winter Park Pines and the area surrounding the Winter Park Village, which offers a quieter and more family-friendly vibe.
  • What are the best apartments with a pool in Winter Park, FL?

  • What are the top cultural and historical sites in Winter Park, FL?

    Winter Park is home to some great cultural and historical sites. The Albin Polasek Museum & Sculpture Gardens showcases the work of the renowned sculptor Albin Polasek, while the Morse Museum, as I mentioned, houses a stunning collection of Tiffany glass. For a glimpse into the city's history, visit the Winter Park Historical Museum, located in a charming old house.
  • What are the best apartments with a jacuzzi in Winter Park, FL?

  • What makes Winter Park, FL unique or famous?

    Winter Park is famous for its beautiful natural setting, with its abundance of lakes and lush greenery. It's also known for its charming, walkable downtown area, lined with boutiques, art galleries, and restaurants. And of course, the city is home to Rollins College, a prestigious liberal arts institution that adds a touch of sophistication and intellectual energy to the area.
  • What are the best apartments for families and kids in Winter Park, FL?

  • Where can you find the best local markets and street food in Winter Park, FL?

    The Winter Park Farmers' Market, held every Saturday morning at the Winter Park Village, is a great place to find local produce, artisanal goods, and a variety of food stalls. For street food, you can check out the food trucks that gather at various locations around town, particularly in the evenings.
  • What are the best pet friendly apartments in Winter Park, FL?

  • How is the public transportation system in Winter Park, FL?

    Winter Park has a public transportation system, but it's not as extensive as in larger cities. The Lynx bus system offers service within the city and to nearby areas, but you'll likely need to rely on taxis or ride-sharing services for more extensive travel.
  • What are the best apartments with parking in Winter Park, FL?

  • Which seasonal events or festivals should apartment renters look forward to in Winter Park, FL?

    Winter Park is known for its lively events. The Winter Park Sidewalk Art Festival, held in March, attracts artists and art lovers from across the country. In December, the city comes alive with holiday cheer during the Winter Park Christmas Parade and other festive events.
  • What amenities are typically included in apartments in Winter Park, FL?

    Apartments in Winter Park often include standard amenities like central air conditioning, a washer and dryer, and a parking space. Some may also offer additional amenities, such as a swimming pool, fitness centre, or community room.
  • What leisure activities are available for relaxation in Winter Park, FL?

    Winter Park offers a variety of leisure activities. You can relax by the lake at Mead Garden, enjoy a leisurely stroll through the scenic trails at the Kraft Azalea Garden, or take a boat ride on one of the many lakes. For a more active experience, you can rent a kayak or canoe and explore the waterways.

Destinations nearby

Best Winter Park, FL holiday apartments with air conditioning

Lake Eola View 1 Bedroom Thornton Park - Winter Park, FL
9.4 308 reviews
Winter Park, FL
28/06 – 18/07
NZ$163/nighttotal: NZ$3260 (20 )

Lake Eola View 1 Bedroom Thornton Park

1 1
apartment , Orlando
This Thornton Park flat in Orlando, Florida overlooks Lake Eola, offering easy access to the Dr. Philips Center for the Performing Arts and the Thornton Park district's restaurants and bars.
The one-bedroom, one-bathroom apartment sleeps two guests and includes a kitchen with fridge, freezer, and microwave, air conditioning, parking, plus Hulu, Netflix, and AT&T cable app access; the owner resides on-site.
Historic Home-  Downtown Orlando - Winter Park, FL
9.5 69 reviews
Winter Park, FL
28/06 – 18/07
NZ$196/nighttotal: NZ$3920 (20 )

Historic Home- Downtown Orlando

1 1
apartment , Orlando
This spacious two-bedroom apartment, situated near Lake Formosa in Orlando, Florida, is approximately 0.5 km from Interstate 4, offering easy access to both Walt Disney World and Daytona Beach, and is within walking distance of the Orlando Science Center and Mennello Museum of American Art.
The self-contained flat, located in a historically significant 1927 Mediterranean Revival home, sleeps two guests and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, parking, and benefits from a peaceful setting adjacent to a jogging trail.
213 Winter Park/downtown Villa+studio Epic Disney - Winter Park, FL
9.7 125 reviews
Winter Park, FL
10/07 – 18/07
NZ$349/nighttotal: NZ$2792 (8 )

213 Winter Park/downtown Villa+studio Epic Disney

1 4
apartment , Fern Park
This Fern Park studio apartment, near the Kissimmee border, offers easy access to major Orlando attractions; Universal Studios is 24 minutes (approx. 38.6km), Disney World 30 minutes (approx. 48.3km), SeaWorld 29 minutes (approx. 46.7km), and Winter Park 15 minutes (approx. 24.1km) away.
Sleeping up to 14 guests, this five-bedroom, three-bathroom self-catering property boasts a fully equipped kitchen, Jacuzzi, garden, high-speed internet (300 Mbps), and free parking; a children's play structure is also available in the large, fenced backyard.
Sunny Oasis: Downtown Orlando With Suburban Feel - Winter Park, FL
10 6 reviews
Winter Park, FL
10/07 – 18/07
NZ$229/nighttotal: NZ$1832 (8 )

Sunny Oasis: Downtown Orlando With Suburban Feel

1 4
apartment , Orlando
This Orlando flat offers a prime location, a short walk from the Milk District and its amenities, with immediate access to the Cady Way and Orlando Urban trails, and is situated 4.8 kilometres from Lake Eola and a 10-minute drive from Orlando Regional Medical Center.
This two-bedroom, two-bathroom apartment accommodates up to four guests, featuring air conditioning, a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher, and a private driveway for parking.

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

The Gojjo Tiny House Walkable Retreat - Winter Park, FL
10 3 reviews
Winter Park, FL
28/07 – 01/08
NZ$332/nighttotal: NZ$1328 (4 )

The Gojjo Tiny House Walkable Retreat

1 2
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.
High-end King Suite Near Everything | Pool & Gym - Winter Park, FL
9.8 10 reviews
Winter Park, FL
23/06 – 28/06
NZ$347/nighttotal: NZ$1735 (5 )

High-end King Suite Near Everything | Pool & Gym

1 2
apartment , Orlando
This modern 1-bedroom apartment in Orlando, Florida, is located 2.4 kilometres from Universal Studios, 2.7 kilometres from Epic Universe, and 4.3 kilometres from Walt Disney World Resort, with downtown Orlando's nightlife, dining, and live music venues like Wall Street Plaza & Church Street an 8-minute walk away.
This pet-friendly accommodation for up to 4 guests offers resort-style amenities including a swimming pool, fitness centre, and rooftop deck, alongside a fully-equipped kitchen with stainless steel appliances and granite countertops, a queen-size sofa bed, a dedicated workspace, and an in-unit washer and dryer.
The Emerald, Milk District Gem! Unit 2 - Winter Park, FL
9.7 28 reviews
Winter Park, FL
28/06 – 18/07
NZ$201/nighttotal: NZ$4020 (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).
Walk To Bars, Coffee, Eat-wrkspace-pet Friendly - Winter Park, FL
9.4 77 reviews
Winter Park, FL
28/06 – 18/07
NZ$278/nighttotal: NZ$5560 (20 )

Walk To Bars, Coffee, Eat-wrkspace-pet Friendly

1 1
apartment , Orlando
This pet-friendly apartment in Orlando's Colonial Town North neighbourhood is conveniently located a 7-minute (approx. 4.5 km) drive from Downtown Orlando, the Amway Center, and other attractions including Church Street and the Orlando Science Centre.
The two-bedroom, two-bathroom ground-floor flat sleeps six, features a dedicated workspace, Roku Smart TVs, and family-friendly amenities such as a stroller, high chair and travel cot (excluding cot bedding), and offers a private entrance.
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