3 Br Near Downtown| Hotub, Pool, Gazebo | Sleeps 7
1 4
apartment , Orlando
This three-bedroom, two-bathroom holiday home is situated near Orlando's Ivanhoe Village and Mills District, offering easy access (within 1.6km) to I-4, Dubsdread Golf Course, and AdventHealth, and approximately 17.7km from Downtown Orlando and the Dr. Phillips Center for the Performing Arts. Sleeping up to eight guests, the property boasts a full kitchen, washer/dryer, high-speed Wi-Fi, a swimming pool, jacuzzi, and parking, plus a unique 'cowboy pool', all within a stylish interior featuring a neutral palette and turquoise accents.
Winter Park, FL
28/06 – 18/07
A$136/nighttotal: A$2720 (20 )
Cozy 2-bedroom Apartment With Ac In Fantastic Orlando
1 1
apartment , Orlando
This Orlando flat is located in the Princeton - Silver Star district, offering convenient access to Tinker Field (3.5 km), Wekiwa Springs State Park (22.8 km), Universal Orlando Resort (7.1 km), Universal Studios Florida (6.9 km), Camping World Stadium (5.2 km), and Kia Center (5.5 km). This one-bedroom, one-bathroom flat accommodates two guests and features air conditioning, heating, and parking, providing a comfortable base for exploring the area's attractions.
10 13 reviews
Winter Park, FL
28/06 – 18/07
A$141/nighttotal: A$2820 (20 )
Elvis Studio Near Ucf | Private | Ev | Parking
1 1
apartment , Goldenrod
Villa Elvis is a luxury studio in Orlando, Goldenrod, situated 16 kilometres from UCF, 24 kilometres from Camping World Stadium, 24 kilometres from Downtown Orlando, and 40 kilometres from Universal Studios. This pet-friendly apartment offers a private entrance, terrace, dedicated workspace, fully equipped kitchen, in-unit laundry, and an on-site EV charger for up to two guests.
9.8 110 reviews
Winter Park, FL
28/06 – 18/07
A$187/nighttotal: A$3740 (20 )
City Charmer
1 1
apartment , Orlando
This half-duplex is situated in Baldwin Park, a peaceful neighbourhood in Orlando, just a short walk from local shops, restaurants, and a grocery store, and only 16 kilometres from Orlando International Airport. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The property offers two bedrooms and two bathrooms, comfortably accommodating up to four guests. It features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, a garden, parking, and air conditioning, as well as internet access for your convenience.
10 15 reviews
Winter Park, FL
10/07 – 18/07
A$288/nighttotal: A$2304 (8 )
The Guest House Orlando
1 4
apartment , Orlando
This Orlando guesthouse is situated in a peaceful, wooded neighbourhood, offering convenient access to the city's attractions, though precise distances aren't specified. Sleeping up to five guests, the self-catering property features two bedrooms, one bathroom with a walk-in shower, a full kitchen with modern appliances, a spacious dining area, and a large garden with a deck – perfect for families.
9.9 226 reviews
Winter Park, FL
28/07 – 01/08
A$274/nighttotal: A$1096 (4 )
Luxury Living Just 3 Blocks From Park Ave!!!
1 2
apartment , Winter Park
This two-bedroom apartment is situated in Winter Park, just 1.6km from the Morse Museum of American Art and 1.5km from Rollins College, offering easy access to the city's cultural attractions and a lively atmosphere. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience. The apartment comfortably accommodates up to four guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher. Enjoy the Florida sunshine with the outdoor pool, spa tub, garden, and terrace, and take advantage of the on-site bar and parking facilities.
Winter Park, FL
28/06 – 18/07
A$171/nighttotal: A$3420 (20 )
Beautiful Flat In Winter Park
1 1
apartment , Winter Park
This Winter Park flat provides excellent access to Orlando's main tourist spots, with major medical facilities and theme parks like Walt Disney World and Universal Orlando Resort a short drive away. This property accommodates up to three guests and features a kitchen, air conditioning, and a swimming pool, making it ideal for exploring Central Florida's dining, shopping, and cultural attractions.
8.8 19 reviews
Winter Park, FL
28/06 – 18/07
A$138/nighttotal: A$2760 (20 )
Sunshine Escape Guesthouse
1 1
apartment , Maitland
This Eatonville holiday home, near Maitland, is conveniently located 2.7km from the RDV Sportsplex and 3.2km from the Enzian Theater, with Lee Road Shopping Centre within a 9.7km radius. The one-bedroom, one-bathroom property sleeps two guests and offers a kitchenette with fridge and microwave, free Wi-Fi, on-site parking, a washer/dryer, and Smart TV; nearby attractions include the Casa Feliz Historic Home Museum.
8.9 44 reviews
Winter Park, FL
28/06 – 18/07
A$142/nighttotal: A$2840 (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.
9.8 104 reviews
Winter Park, FL
28/06 – 18/07
A$213/nighttotal: A$4260 (20 )
Lakefront Artist's Loft - Relax In Luxury!
1 1
apartment , Orlando
This charming house is located in College Park, a short distance from the Camping World Stadium, Kia Center, and Orlando Science Center, offering easy access to the city's attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The house is a comfortable and well-equipped property, with 28 square metres of space and a capacity of two guests. Enjoy a private pool, a spa tub, and a garden, perfect for relaxing after a day of exploring the city.
9.6 47 reviews
Winter Park, FL
23/06 – 28/06
A$122/nighttotal: A$610 (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.
10 2 reviews
Winter Park, FL
28/07 – 01/08
A$90/nighttotal: A$360 (4 )
Hogar Sobre Ruedas
1 2
apartment , Rio Pinar
This self-catering apartment in Orlando's Rio Pinar neighbourhood is conveniently located approximately 15-21 kilometres from attractions such as Church Street Station, the Kia Center, Camping World Stadium, and the Holy Land Experience. The one-bedroom, one-bathroom flat sleeps three guests and features a private terrace with garden views, free Wi-Fi, private parking, air conditioning, and a fully equipped kitchen.
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
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.
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.
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.
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
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.
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.
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).
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.
Frequently asked questions about apartment rentals in Winter Park, FL
What are the top cultural and historical sites in Winter Park, FL?
Winter Park is full of history and culture. The Albin Polasek Museum & Sculpture Gardens is a must-see for art lovers, showcasing the work of the renowned sculptor. And the Winter Park Historical Society Museum offers a fascinating glimpse into the city's past, with exhibits on its early settlers and development.
Winter Park is known for its charming, walkable downtown with beautiful architecture and lush landscaping. It's also home to several renowned museums, including the Morse Museum and the Albin Polasek Museum, and the beautiful Rollins College campus adds a vibrant atmosphere. And of course, Winter Park is famous for its beautiful chain of lakes and its many opportunities for outdoor recreation.
What are the best apartments with a pool 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, artisan crafts, and delicious food from local vendors. Park Avenue also has several restaurants and cafes offering a variety of cuisines.
What are the best apartments with a jacuzzi in Winter Park, FL?
How is the public transportation system in Winter Park, FL?
Winter Park has a decent public transportation system, with the Lynx bus service running through the city. However, for getting around within the city, walking or cycling is often the easiest and most enjoyable option, especially in the downtown area.
What are the best apartments for families and kids in Winter Park, FL?
What amenities are typically included in apartments in Winter Park, FL?
Apartments in Winter Park typically include basic amenities like central air conditioning, a refrigerator, and a stove. Many also offer laundry facilities, either in-unit or on-site. Some luxury apartments may include additional features like a swimming pool, fitness centre, or parking.
What are the best pet friendly apartments in Winter Park, FL?
Best Winter Park, FL holiday apartments with air conditioning
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.
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.
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.
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
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.
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.
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.
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.