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

Salt Pool, Cozy House Near Downtown And International Airport - Winter Park, FL
9.6 99 reviews
Winter Park, FL
08/01 – 29/01
NZ$301/nighttotal: NZ$6321 (21 )

Salt Pool, Cozy House Near Downtown And International Airport

3 2
apartment , Orlando
This three-bedroom apartment is located in Dixie Belle, a neighbourhood in Orlando, just 10 kilometres from the city centre and 10 kilometres from Orlando International Airport. The property has excellent user ratings and is highly recommended for families and groups.
The apartment has a split floorplan with its own private access to the outdoor pool, providing a sense of seclusion. It comfortably sleeps six guests and features a fully equipped kitchen, a family living room, a private backyard with a pool, a brand-new grill, and a spa.
Sleeps 8-3 Bedrooms 2 Full Bathroms+gameroom Your Perfect Vacation Home! - Winter Park, FL
9.8 49 reviews
Winter Park, FL
28/07 – 01/08
NZ$349/nighttotal: NZ$1396 (4 )

Sleeps 8-3 Bedrooms 2 Full Bathroms+gameroom Your Perfect Vacation Home!

3 2
apartment , Casselberry
This Casselberry holiday home is situated approximately 32 kilometres from Downtown Orlando and offers easy access to Wekiva Springs State Park and Blue Springs State Park.
The three-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, game room with pool table and air hockey, plus access to a nearby neighbourhood pool and free Wi-Fi.
Private 3-bedroom Condo On Luxury Golf Course In Orlando + Pool, Gym, Golf & Fun - Winter Park, FL
Winter Park, FL
03/07 – 31/07
NZ$231/nighttotal: NZ$6468 (28 )

Private 3-bedroom Condo On Luxury Golf Course In Orlando + Pool, Gym, Golf & Fun

3 2
apartment , Orlando
This three-bedroom, two-bathroom holiday flat is located within Orlando's exclusive Ventura Country Club, offering lake views and convenient access to dining, shopping at Florida Mall and Orlando International Premium Outlets, entertainment, and the MCO airport, all within a 5-kilometre radius.
This family-friendly apartment accommodates up to six guests and features a fully equipped kitchen, air conditioning, Wi-Fi, a Jacuzzi tub, and access to country club amenities including a swimming pool, gym, library, tennis courts, and an 18-hole golf course, with a private balcony providing a perfect spot to enjoy the surroundings.
5 Sodo Home, Guest Fave,petsok, Game Room, Bbq, Fire Pit,netflix, Popcorn Maker - Winter Park, FL
10 23 reviews
Winter Park, FL
23/06 – 28/06
NZ$989/nighttotal: NZ$4945 (5 )

5 Sodo Home, Guest Fave,petsok, Game Room, Bbq, Fire Pit,netflix, Popcorn Maker

4 2
apartment , Orlando
This Orlando property, located in the Wadeview Park neighbourhood, is a 4-minute drive from the Dr Phillips Center for the Performing Arts and Orange Avenue.
The 139 square metre (1496 square feet) house sleeps up to 10 guests and boasts 4 bedrooms, 3 bathrooms, a fully equipped kitchen with dishwasher and microwave, in-unit laundry, Wi-Fi, and secure parking; barbecue facilities are also available on-site.

Best Winter Park, FL holiday apartments with a kitchen

𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ - Winter Park, FL
9.7 157 reviews
Winter Park, FL
03/09 – 08/09
NZ$300/nighttotal: NZ$1500 (5 )

𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ

1 2
apartment , Fairview Shores
This two-bedroom apartment is situated in the peaceful Winter Park neighbourhood, just a short distance from major theme parks, downtown Orlando, and the Avenue, making it an ideal base for exploring the city. The property has received excellent ratings for its cleanliness, location, and overall guest experience.
The apartment is spacious and comfortably sleeps up to eight guests, with three queen beds and a pull-out sofa. Guests can enjoy modern amenities, including high-speed Wi-Fi, a smart TV with streaming services, a washer/dryer, and free designated parking.
Cozy Downtown Living Sleeps 8 W/ Free Parking - Winter Park, FL
9.7 79 reviews
Winter Park, FL
10/07 – 18/07
NZ$294/nighttotal: NZ$2352 (8 )

Cozy Downtown Living Sleeps 8 W/ Free Parking

1 4
apartment , Orlando
This two-bedroom house is situated in downtown Orlando, within walking distance of Lake Eola Park.
The property, sleeping up to eight guests, boasts a fully equipped kitchen with quartz countertops, stainless steel appliances, and a bonus room with a pull-out sofa bed and workstation; two free parking spaces are also provided.
Lake Marion Apt With Canoe In Altamonte Springs! - Winter Park, FL
9.8 188 reviews
Winter Park, FL
08/01 – 29/01
NZ$228/nighttotal: NZ$4788 (21 )

Lake Marion Apt With 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.
Modern 3/2 In Ivanhoe Village - Winter Park, FL
9.9 180 reviews
Winter Park, FL
08/01 – 29/01
NZ$189/nighttotal: NZ$3969 (21 )

Modern 3/2 In Ivanhoe Village

1 2
apartment , Orlando
This newly renovated three-bedroom duplex in Orlando's Ivanhoe Village offers easy access to the city's best restaurants and entertainment.
Sleeping eight guests, the property boasts a private patio with BBQ, fire pit, and hammock, plus a fully equipped kitchen, in-unit laundry, and secure keyless entry.

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

Greatest Location In Winter Park! (4) - Winter Park, FL
9.5 68 reviews
Winter Park, FL
03/07 – 31/07
NZ$213/nighttotal: NZ$5964 (28 )

Greatest Location In Winter Park! (4)

2 2
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.
Priv. Modern Cozy Cp 1b/1ba Suite Near Dt Orl & Wp - Winter Park, FL
9.9 158 reviews
Winter Park, FL
23/06 – 28/06
NZ$189/nighttotal: NZ$945 (5 )

Priv. Modern Cozy Cp 1b/1ba Suite Near Dt Orl & Wp

1 2
apartment , Orlando
This Orlando guesthouse is situated in the College Park neighbourhood, a short 8km drive from Dubsdread Golf Course and local shops, and within 16km of Orlando city centre.
The modern 2021 townhome sleeps two guests in one bedroom with a queen-size bed, private bathroom, and in-room amenities including a mini-fridge, microwave, and Roku smart TV; guests also enjoy access to a private patio and on-site parking.
At Mine - Orlando King Suite - Winter Park, FL
10 3 reviews
Winter Park, FL
23/06 – 28/06
NZ$168/nighttotal: NZ$840 (5 )

At Mine - Orlando King Suite

1 2
apartment , Maitland
This Maitland flat offers convenient access to local attractions and amenities within its district.
This one-bedroom apartment for two features a king-size bed, a private balcony, and access to an outdoor pool, hot tub, and fitness centre, with covered parking available for £18 per day.
"The Sweet Suite" - Private & Quiet, Near 408/417 - Winter Park, FL
10 16 reviews
Winter Park, FL
28/07 – 01/08
NZ$167/nighttotal: NZ$668 (4 )

"The Sweet Suite" - Private & Quiet, Near 408/417

1 2
apartment , Azalea Park
This one-bedroom flat in East Orlando is conveniently located just 20-30 minutes from Orlando's theme parks and attractions, offering easy access to the city's excitement. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The 30 square metre apartment comfortably accommodates two guests and features a modern kitchen with a full-size fridge, cooktop, and all the necessary equipment for self-catering. You'll also enjoy a private garden, a spa, and a large flat-screen TV for entertainment.

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

New Renovated House Near Everything - Winter Park, FL
9.1 43 reviews
Winter Park, FL
28/06 – 18/07
NZ$172/nighttotal: NZ$3440 (20 )

New Renovated House Near Everything

1 1
apartment , Eatonville
This centrally located apartment in Eatonville is within easy reach of the town's attractions, making it a great base for exploring. It has consistently received excellent ratings for cleanliness, location, and overall experience, ensuring a comfortable stay.
The apartment features three bedrooms and two bathrooms, comfortably accommodating up to five guests. It comes equipped with a modern kitchen, a garden, and parking, offering everything you need for a relaxing and enjoyable trip.
The Bird House Spa Winter Park - Winter Park, FL
9.9 91 reviews
Winter Park, FL
03/07 – 10/07
NZ$450/nighttotal: NZ$3150 (7 )

The Bird House Spa Winter Park

1 2
apartment , Casselberry
This luxurious four-bedroom, two-bathroom property in Winter Park, a short drive from Casselberry, offers easy access to Park Avenue's shops and restaurants.
Sleeping up to ten guests, this holiday home boasts a gourmet kitchen, a Clearlight sauna with cold plunge, an eight-person hot tub, a game room with pool table, foosball, and air hockey, plus uniquely themed bedrooms and smart home technology.
Tranquil Hideaway: 2-bedroom Retreat Near Mills/50 - Winter Park, FL
9.4 3 reviews
Winter Park, FL
03/07 – 10/07
NZ$236/nighttotal: NZ$1652 (7 )

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.
Luxury 3bd In Downtown Orlando - Winter Park, FL
10 1 review
Winter Park, FL
08/01 – 29/01
NZ$304/nighttotal: NZ$6384 (21 )

Luxury 3bd In Downtown Orlando

3 2
apartment , Orlando
This apartment is situated in College Park, Orlando, just across the street from Dubsdread Golf Course and within easy reach of Universal Orlando Resort, Disney World, and SeaWorld, all within a 10-15 kilometre radius. The surrounding area is pleasant and peaceful, offering a welcome break from the hustle and bustle of the theme parks.
The flat has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes equipped with a microwave oven, dishwasher, air conditioning, a jacuzzi, parking, and internet access, as well as a private patio and fenced yard, ideal for relaxing in the Florida sunshine.
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