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

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

Drayton Place Staycation - Private Lk/pk Front Ste - Winter Park, FL
9.3 40 reviews
Winter Park, FL
10/07 – 18/07
A$338/nighttotal: A$2704 (8 )

Drayton Place Staycation - Private Lk/pk Front Ste

2 4
apartment , Orlando
This waterfront holiday home is located just 1.6 kilometres from the Kia Center, within a 10-minute walk of Camping World Stadium and Tinker Field. It has excellent user, location and cleanliness ratings.
The property offers two bedrooms and a bathroom, covering 42 square metres and accommodating up to four guests. It has a range of amenities including a swimming pool, spa, garden, terrace, and a fully equipped kitchen.
Florida Vacation With Pool Fun For Families - Winter Park, FL
9.4 42 reviews
Winter Park, FL
28/07 – 01/08
A$289/nighttotal: A$1156 (4 )

Florida Vacation With Pool Fun For Families

4 2
apartment , Casselberry
This charming three-bedroom house is located in Casselberry, just 5km from Altamonte Mall and within 10km of Cranes Roost Park and Red Bug Lake Park, offering easy access to shopping and outdoor activities. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The house comfortably accommodates up to 7 guests and provides a fully equipped kitchen, a private pool, a garden with barbecue facilities, and free Wi-Fi. Enjoy the Florida sunshine with al fresco dining and relax by the pool, while exploring the nearby golf courses and parks.
The Gojjo Retreat - Private Home Walkable Retreat - Winter Park, FL
9.9 14 reviews
Winter Park, FL
28/07 – 01/08
A$225/nighttotal: A$900 (4 )

The Gojjo Retreat - Private Home Walkable Retreat

1 2
apartment , Orlando
This brand new 2025 luxury tiny home in Orlando offers a tranquil urban oasis, located within 500 meters of top dining establishments and close to the city's attractions.
This one-bedroom, one-bathroom flat accommodates up to four guests, featuring air conditioning, Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, plus off-street parking and a communal fire pit area.
Winter Park Citrus Escape; Sleeps 8, Relaxing Pool, Family & Pet Friendly - Winter Park, FL
8.8 30 reviews
Winter Park, FL
10/07 – 18/07
A$469/nighttotal: A$3752 (8 )

Winter Park Citrus Escape; Sleeps 8, Relaxing Pool, Family & Pet Friendly

3 4
apartment , Goldenrod
This apartment is situated in Goldenrod, a neighbourhood in Winter Park, just 15-20 minutes from Orlando International Airport and 30-45 minutes from theme parks like Disney World, Universal Studios and SeaWorld. The property has received excellent user ratings, making it a popular choice for visitors to the area.
This home can accommodate up to eight guests, offering three bedrooms and two bathrooms. The property features a fully equipped kitchen, air conditioning, a swimming pool, and parking, as well as amenities like a ping pong table, foosball table, board games, and a screened-in covered back patio.

Best Winter Park, FL holiday apartments with a kitchen

Yale House In College Park 2 Mi From Downtown - Winter Park, FL
9.9 115 reviews
Winter Park, FL
28/06 – 18/07
A$353/nighttotal: A$7060 (20 )

Yale House In College Park 2 Mi From Downtown

1 1
apartment , Orlando
This charming apartment is located in a peaceful neighbourhood just 2 kilometres from downtown Orlando, close to shops, restaurants, and a grocery store. It has received excellent ratings for location, cleanliness, and user experience.
The two-bedroom flat can accommodate up to four guests and features a spacious living room, a fully equipped kitchen, and a dedicated workspace. It also offers a range of amenities including a Jacuzzi, a garden, a fitness centre, and a private gym in a detached garage.
Mid Term Rental 2 Bedroom Retreat Steps To Lake Eola Thornton Park - Winter Park, FL
10 1 review
Winter Park, FL
28/06 – 18/07
A$201/nighttotal: A$4020 (20 )

Mid Term Rental 2 Bedroom Retreat Steps To Lake Eola Thornton Park

2 1
apartment , Orlando
This two-bedroom flat is located in Orlando's Thornton Park district, a short walk from Lake Eola and 1.77 kilometres from the Kia Centre.
This 79 square metre apartment offers air conditioning, complimentary WiFi, private parking, and a fully equipped kitchen, accommodating up to seven guests for mid-term stays.
The Emerald, Milk District Gem! Unit 2 - Winter Park, FL
9.7 28 reviews
Winter Park, FL
28/06 – 18/07
A$166/nighttotal: A$3320 (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).
Chic Studio Near Downtown & Theme Parks - Winter Park, FL
Winter Park, FL
28/06 – 18/07
A$93/nighttotal: A$1860 (20 )

Chic Studio Near Downtown & Theme Parks

1 1
studio , Orlando
This Orlando apartment is situated approximately 8.5 kilometres from Church Street Station and 8.7 kilometres from the Kia Centre, offering convenient access to downtown landmarks.
This 37 square metre studio apartment accommodates up to three guests and features a kitchenette with a microwave, complimentary WiFi, air conditioning, and a garden area, with Orlando International Airport located just 10.9 kilometres away.

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Best Winter Park, FL holiday apartments with air conditioning

Premium King Suite With Den In Central Orlando | P - Winter Park, FL
9.8 16 reviews
Winter Park, FL
28/06 – 01/07
A$359/nighttotal: A$1077 (3 )

Premium King Suite With Den In Central Orlando | P

1 4
apartment , Orlando
This 1-bedroom plus den flat is located in Downtown Orlando, 5 minutes from Lake Eola, the Dr. Phillips Centre for the Performing Arts, and the Kia Centre, with Universal Studios 24 kilometres away and Walt Disney World Resort 43 kilometres away.
This pet-friendly apartment offers resort-style amenities including a swimming pool and fitness centre, a fully-equipped kitchen with stainless steel appliances, and accommodates up to four guests with a king-size bed in the master bedroom and a queen-size bed in the den.
Chris & Tish Cozy Apartments -1 Bedroom With Queen Size Bed. - Winter Park, FL
Winter Park, FL
28/06 – 18/07
A$138/nighttotal: A$2760 (20 )

Chris & Tish Cozy Apartments -1 Bedroom With Queen Size Bed.

1 1
apartment , Eatonville
This Maitland apartment, near Eatonville, is conveniently located 2 km from the Casa Feliz Historic Home Museum, 20 km from Wekiwa Springs State Park, and 19 km from Tinker Field.
The one-bedroom, one-bathroom flat sleeps two guests and includes Wi-Fi, air conditioning, and access to nearby attractions such as Universal Studios and the Wizarding World of Harry Potter.
Adorable 1-bedroom Home W/ Full Kitchen & Parking - Sleeps 4 - Winter Park, FL
9.6 162 reviews
Winter Park, FL
28/06 – 01/07
A$256/nighttotal: A$768 (3 )

Adorable 1-bedroom Home W/ Full Kitchen & Parking - Sleeps 4

1 4
apartment , Orlando
This one-bedroom apartment is located in Colonialtown South, just 800 metres from Lake Eola and within 5 kilometres of the Kia Center and Camping World Stadium. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 73 square metres and includes a fully equipped kitchen, a terrace, and a garden. It also offers amenities like free Wi-Fi, parking, air conditioning, and a designated smoking area, making it a comfortable and convenient base for exploring Orlando.
Sleeps 3, Winter Park & Downtown - Winter Park, FL
9.6 128 reviews
Winter Park, FL
28/07 – 01/08
A$193/nighttotal: A$772 (4 )

Sleeps 3, Winter Park & Downtown

1 2
apartment , Fairview Shores
This one-bedroom apartment is situated in Winter Park, a short distance from the College Park neighbourhood and a 40-kilometre drive from Orlando's major theme parks.
The self-catering property features a fully equipped kitchen, a modern bathroom, and can comfortably accommodate up to four guests, making it an ideal choice for families or groups of friends visiting Fairview Shores.

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

Walk To Bars, Coffee, Eateries-king Bed-workspace - Winter Park, FL
9.6 76 reviews
Winter Park, FL
10/07 – 18/07
A$195/nighttotal: A$1560 (8 )

Walk To Bars, Coffee, Eateries-king Bed-workspace

1 4
apartment , Orlando
This two-bedroom Orlando apartment is situated in the Colonial Town North neighbourhood, a 4.5km drive from Downtown Orlando, Amway Center and other attractions.
The self-catering property sleeps six, features two queen beds with Roku Smart TVs, a private entrance, and family-friendly amenities including a stroller, pack 'n play and high chair; nearby restaurants include Mamak Asian Street Food and Sushi Noodle & Grill.
3-bedroom Peaceful Longwood Home  Minutes To Attractions - Netflix - Location - Winter Park, FL
10 3 reviews
Winter Park, FL
10/07 – 18/07
A$238/nighttotal: A$1904 (8 )

3-bedroom Peaceful Longwood Home Minutes To Attractions - Netflix - Location

3 4
apartment , Longwood
This Longwood flat is situated in a quiet residential area, offering easy access to local dining, shopping, golf courses, and is a short drive to Orlando's theme parks and the downtown area, with nearby parks and nature preserves for outdoor pursuits.
This family-friendly accommodation sleeps up to 8 guests across three queen-sized bedrooms and features a fully equipped kitchen with a microwave oven and dishwasher, air conditioning, and parking, with a check-out time of 11:00 AM.
8th Green Cottage "A Relaxing Oasis In The City" Guesthouse - Winter Park, FL
9.2 44 reviews
Winter Park, FL
28/07 – 01/08
A$243/nighttotal: A$972 (4 )

8th Green Cottage "A Relaxing Oasis In The City" Guesthouse

2 2
apartment , Orlando
This two-bedroom house is located in College Park, just 2km from Dubsdread Golf Course, Lee Road Shopping Center, and AdventHealth Orlando, offering a peaceful escape from the bustling tourist attractions. It has consistently received excellent ratings from previous guests.
The 79 square metre property can comfortably accommodate up to four guests and features a fully equipped kitchen, a private garden, a swimming pool, a jacuzzi, and a terrace. Relax in the spa tub after a day exploring Orlando's attractions, or enjoy the Florida sunshine in the private garden.
Cozy 1-bedroom House In Lovely Orlando With Ac - Winter Park, FL
Winter Park, FL
28/06 – 18/07
A$225/nighttotal: A$4500 (20 )

Cozy 1-bedroom House In Lovely Orlando With Ac

1 1
apartment , Rio Pinar
This one-bedroom flat in Rio Pinar, Orlando, offers convenient access to Florida Mall and Mall at Millenia, both within a 2 kilometre drive, and is a short 5 kilometre journey to Universal Orlando Resort and Universal Epic Universe.
This rental property accommodates two guests with a king-sized bed, features air conditioning and heating, and provides internet access, with hosts available to assist with any enquiries.
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