This Fairview Shores house, located minutes from Lake Eola and Park Avenue in Winter Park, offers easy access to Mills 50 and major highways, with Orlando's theme parks approximately 40km away. Sleeping up to 11 guests, this three-bedroom property boasts a fully equipped kitchen, a Roku-enabled TV, a fenced backyard with BBQ, and free parking for 3-4 vehicles; a master suite includes an ensuite bathroom and washer-dryer.
10 15 reviews
Winter Park, FL
28/06 – 18/07
99 €/nighttotal: 1980 € (20 )
Lake Eola View 1 Bedroom Thornton Park
1 1
apartment , Orlando
This Orlando apartment, situated in the South Eola district, offers lakefront views and is conveniently located near Thornton Park's restaurants and the Dr. Philips Center for the Performing Arts, with major attractions such as Universal Orlando Resort and the Florida Mall within a reasonable driving distance (distances vary depending on traffic). The one-bedroom, one-bathroom flat sleeps two guests and includes a kitchen with a fridge and microwave, air conditioning, parking, internet access, and in-unit streaming services (Hulu, Netflix, and AT&T TV app).
9.9 35 reviews
Winter Park, FL
14/08 – 21/08
129 €/nighttotal: 903 € (7 )
Modern 3br | Walk To Restaurants, Bars & Publix
3 2
apartment , Orlando
This Orlando apartment rental is situated in the Mills 50 district, a short drive (approx. 32km) from Walt Disney World and 16km from Universal Studios Florida, offering easy access to Kadence, a Michelin-starred restaurant, and a Publix supermarket. The three-bedroom, two-and-a-half-bathroom property sleeps eight guests, features a fully equipped kitchen, private backyard with BBQ, and a dedicated workspace; enjoy nearby bars and restaurants, plus Lake Eola Park (approx. 10km).
9.7 162 reviews
Winter Park, FL
28/06 – 01/07
167 €/nighttotal: 501 € (3 )
𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ
2 4
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.
9.9 61 reviews
Winter Park, FL
28/07 – 01/08
123 €/nighttotal: 492 € (4 )
Fern Park Retreat
1 2
apartment , Maitland
This renovated 1958 guest house, situated in the Fern Park district of Maitland, Seminole County, is less than 1.6km from the SunRail station and offers easy access to major highways and Orlando attractions. The self-contained property sleeps two guests in two bedrooms and one bathroom, boasting a modern kitchen with dishwasher, air conditioning, a private fenced garden, and parking; kayaks and a BBQ are available on request.
9.8 109 reviews
Winter Park, FL
28/06 – 18/07
121 €/nighttotal: 2420 € (20 )
Winter Park Guest Suite |Near Ucf/fullsail/rollins
1 1
apartment , Goldenrod
This charming guesthouse is situated in a central Winter Park neighbourhood, just a short drive from UCF, Rollins College, Full Sail, and Park Avenue. The property consistently receives excellent ratings for its cleanliness, location, and overall experience. The self-contained suite is attached to the main house but has its own private entrance, accommodating up to two guests. The suite includes a fully equipped kitchen with a fridge, freezer, microwave, and cooktop, as well as air conditioning and parking.
9.9 75 reviews
Winter Park, FL
10/07 – 18/07
211 €/nighttotal: 1688 € (8 )
Charming Bungalow In Winter Park
3 4
apartment , Orlando
This Orwin Manor bungalow offers three bedrooms and two bathrooms, comfortably sleeping six guests, and is conveniently located near Orlando's hospitals and downtown, providing easy access to local restaurants. The 160 square metre single-family home boasts an open-plan layout, hardwood floors, a fully equipped kitchen including a dishwasher, air conditioning, ample parking, and a landscaped yard; emotional support animals are permitted for an additional fee.
Winter Park, FL
14/08 – 21/08
128 €/nighttotal: 896 € (7 )
Apartment ∙ 1 Bedroom ∙ 3 Guests
1 2
apartment , Orlando
This one-bedroom flat offers a European neo-classic decor and is conveniently located 8 kilometres from Orlando International Airport and close to Downtown Orlando, with Magic Kingdom, Epcot, Animal Kingdom approximately 40 kilometres away and Universal Studios around 32 kilometres away. This family-friendly apartment accommodates up to three guests and features a fully equipped kitchen, complimentary toiletries, bed linens, towels, laundry facilities, free parking for two cars, super-fast Wi-Fi, a 50-inch Smart TV with streaming services, and a communal swimming pool, all within a residential community with an attached Walmart for convenience.
9.7 28 reviews
Winter Park, FL
28/06 – 18/07
113 €/nighttotal: 2260 € (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).
9.9 122 reviews
Winter Park, FL
28/06 – 18/07
120 €/nighttotal: 2400 € (20 )
The Emerald | Walk To Downtown Orlando & Lake Eola
2 1
apartment , Orlando
This charming apartment is located in Downtown Orlando, just 15 kilometres from Universal Studios and the airport. It has received excellent ratings for cleanliness, location, and user experience. The apartment, which can comfortably accommodate four guests, features a spacious living area and a well-equipped kitchen. It also offers amenities such as a private entrance, on-site parking, and a rainforest shower, making it a perfect choice for those looking for a comfortable and convenient stay in Orlando.
9.3 165 reviews
Winter Park, FL
28/06 – 18/07
76 €/nighttotal: 1520 € (20 )
Cute And Cozy Studio W/ Jacuzzi!
1 1
apartment , Orlando
This newly remodelled studio flat in Orlando, Florida, is situated a few minutes from the airport and downtown area, placing Universal Studios and Walt Disney World within a 22.5 to 33.8 kilometre radius. This pet-friendly accommodation for two guests features a private, fenced patio with a jacuzzi and fire pit, a kitchenette equipped with a hot plate and air fryer, and free parking for two vehicles.
Winter Park, FL
28/06 – 18/07
92 €/nighttotal: 1840 € (20 )
Lake Eola View 1 Bedroom Thornton Park
1 1
apartment , Orlando
This one-bedroom flat in Orlando's Thornton Park district offers views of Lake Eola and is located 1.1 kilometres from the city centre, a 17-minute walk to Church Street Station, 1.8 kilometres from the Kia Centre, and 3.9 kilometres from Camping World Stadium. This apartment provides complimentary WiFi, private parking, and a fully equipped kitchen, accommodating up to three guests with a private entrance and being 14.9 kilometres from Orlando International Airport.
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
10 36 reviews
Winter Park, FL
28/06 – 01/07
257 €/nighttotal: 771 € (3 )
Charming Clean Home Near East End Market Large Fenced Yard
3 4
apartment , Winter Park
This family-friendly house is located in the heart of Orlando, just 1.6 kilometres from Harry P. Leu Gardens and Lake Virginia, offering easy access to the city's attractions. The property is highly rated by previous guests, receiving an excellent rating for its comfort and amenities. The house spans 111 square metres and comfortably accommodates up to six guests in its three bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a garden with barbecue facilities, and a terrace or balcony for relaxing and enjoying the sunshine.
10 56 reviews
Winter Park, FL
28/07 – 01/08
189 €/nighttotal: 756 € (4 )
Stylish & Cozy King Bed Retreat @ Baldwin Park
1 2
apartment , Orlando
This fully furnished two-bedroom house is situated near Baldwin Park, a short drive (minutes) from Downtown Orlando, Orlando International Airport (MCO), and several theme parks. The 2-bathroom property, sleeping up to 5 guests, boasts a private backyard with a fire pit, high-speed internet, a fully equipped kitchen including a dishwasher, and keyless entry; peaceful walking trails are also nearby, with Downtown Disney easily accessible.
9.8 138 reviews
Winter Park, FL
28/06 – 18/07
205 €/nighttotal: 4100 € (20 )
Updated Home* 2 King Bed Suites * Downtown Orlando
2 1
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.
Winter Park, FL
10/07 – 18/07
118 €/nighttotal: 944 € (8 )
76 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests
2 4
apartment , Orlando
This two-bedroom condo in Orlando offers a family-friendly base with convenient access to Universal Orlando Resort, SeaWorld Orlando, and Orlando International Airport, located within 19 kilometres of the latter. This 76 square metre apartment accommodates up to four guests and features a full kitchen, a private balcony, and access to resort amenities including a swimming pool, fitness centre, and pickleball courts.
Best Winter Park, FL holiday apartments with a kitchen
9.6 111 reviews
Winter Park, FL
28/06 – 01/07
151 €/nighttotal: 453 € (3 )
Centrally Located Orlando Home
1 4
apartment , Fern Park
This stylish three-bedroom house in Fern Park, a quiet Orlando suburb, is located approximately 15-25 km from Full Sail University, Rollins College, and downtown Orlando. The 3-bedroom, 2-bathroom property sleeps six guests and features a fully equipped kitchen with stainless steel appliances, a garden, parking, keyless entry, and is within walking distance of Kewanee Park; a washer/dryer is available at an extra cost.
9.7 83 reviews
Winter Park, FL
10/07 – 18/07
148 €/nighttotal: 1184 € (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.
8.7 6 reviews
Winter Park, FL
28/06 – 18/07
71 €/nighttotal: 1420 € (20 )
Botanical Tranquility
1 1
apartment , Casselberry
This Casselberry apartment is conveniently located approximately 17-24 km from various Orlando attractions including Orlando Sanford International Airport, Addition Financial Arena, and the Florida Mall. The self-catering flat offers one bedroom, one bathroom, sleeps three guests, and boasts a private pool, free Wi-Fi, and parking; nearby activities include visiting the Amway Center and Camping World Stadium.
8.8 20 reviews
Winter Park, FL
28/06 – 18/07
59 €/nighttotal: 1180 € (20 )
Chic Downtown Orlando Studio
1 1
apartment , Orlando
This Orlando studio flat offers a prime downtown location, just 200 meters from Lake Eola Park, putting you within walking distance of numerous cafes, restaurants, and entertainment venues. This newly remodelled studio accommodates up to two guests with a fully equipped kitchenette, Wi-Fi, air conditioning, and complimentary parking for one vehicle, making it ideal for a comfortable stay.
Frequently asked questions about apartment rentals in Winter Park, FL
What are the top cultural and historical sites in Winter Park, FL?
Winter Park has a rich history. The Albin Polasek Museum & Sculpture Gardens is a must-see for art lovers. For history buffs, the Winter Park History Museum is a great place to learn about the city's past. You'll also find a lot of historic architecture in the area, particularly along Park Avenue.
Winter Park is known for its beautiful lakes, lush greenery, and charming atmosphere. The city is home to a number of beautiful parks, including Central Park, which is a great place for a picnic or a stroll. Winter Park is also home to Rollins College, a prestigious liberal arts college that adds to the city's intellectual and cultural vibrancy.
What are the best apartments with a pool in Winter Park, FL?
How is the public transportation system in Winter Park, FL?
Winter Park has a good public transportation system, with Lynx buses running throughout the city and connecting to other parts of the Orlando area. You can also find a few SunRail stations in the area, which provide train service to other parts of Central Florida.
What are the best apartments with a jacuzzi in Winter Park, FL?
Which seasonal events or festivals should apartment renters look forward to in Winter Park, FL?
You should look forward to the Winter Park Sidewalk Festival, which is held every month on Park Avenue, and the Winter Park Art Festival, held annually in March. The Winter Park Boat Show is also a popular event, held in November.
What are the best apartments for families and kids in Winter Park, FL?
What leisure activities are available for relaxation in Winter Park, FL?
Winter Park offers a lot of opportunities for relaxation. You can rent a kayak or canoe and explore the many lakes and canals in the area. Or, you can simply relax and enjoy the scenery at one of the many parks in the city, like Central Park or Mead Garden.
What are the best pet friendly apartments in Winter Park, FL?
Best Winter Park, FL holiday apartments with air conditioning
9.8 86 reviews
Winter Park, FL
10/07 – 18/07
134 €/nighttotal: 1072 € (8 )
2 Min To Park Ave | Charming Winter Park Bungalow
1 4
apartment , Fairview Shores
This apartment is located in Winter Park, a charming neighbourhood just 2 kilometres from Park Avenue and its diverse dining scene, and 40 kilometres from Orlando International Airport. It has received excellent ratings for its location, cleanliness, and overall user experience. The apartment can comfortably accommodate up to four guests and features a spacious and open layout. Guests can enjoy a peaceful outdoor patio, a well-equipped kitchen, air conditioning, a garden, a fitness centre, and parking.
8.0 12 reviews
Winter Park, FL
10/07 – 18/07
140 €/nighttotal: 1120 € (8 )
2/1 With Private Backyard In The Heart Of Ivanhoe
2 4
apartment , Orlando
This two-bedroom flat is situated in Orlando's Village Ivanhoe district, a mere 300 metres from Lake Ivanhoe and 960 metres from the Orlando Science Center, with AdventHealth Station 1.1 kilometres away for public transport access. This accommodation for up to eight guests offers a fully equipped kitchen, on-site parking, free Wi-Fi, television, and laundry facilities, and is conveniently located for visiting Universal Orlando Resort.
9.0 42 reviews
Winter Park, FL
28/07 – 01/08
131 €/nighttotal: 524 € (4 )
️Walk To Lake Eola & Restaurants
2 2
apartment , Orlando
This Thornton Park flat is less than 1.6km from Lake Eola and the Dr. Phillips Center for the Performing Arts, and within 4.8km of Camping World Stadium. This two-bedroom, one-bathroom apartment sleeps four, includes in-unit laundry, and offers excellent access to Thornton Park's restaurants and shops.
10 2 reviews
Winter Park, FL
28/06 – 01/07
153 €/nighttotal: 459 € (3 )
Cozy Orlando Home Close To Parks, Dining, And Downtown Fun
2 4
apartment , Orlando
This Orlando apartment, situated in the Lawsona-Fern Creek neighbourhood, is a 13-minute walk (approximately 1km) from Lake Eola Park and offers easy access to attractions such as the Florida Mall and Universal Orlando Resort. The two-bedroom, one-bathroom property sleeps six guests and features a fully equipped kitchen with dishwasher, a terrace, air conditioning, Wi-Fi, and a workspace, perfect for families or groups visiting the city.
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
10 277 reviews
Winter Park, FL
28/06 – 01/07
315 €/nighttotal: 945 € (3 )
Family & Pet Friendly (*Additional Pet Fee Applies), Charming Orlando Home!
2 4
apartment , Orlando
This charming three-bedroom cottage is located in a safe and peaceful neighbourhood just a short distance from Orlando's main attractions. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience. The spacious 163 square metre dwelling can comfortably accommodate up to eight guests. It features a fully equipped kitchen, a zen garden, a private backyard with a pergola and a propane grill, as well as an Xbox for entertainment.
8.0 1 review
Winter Park, FL
28/06 – 18/07
332 €/nighttotal: 6640 € (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.
Winter Park, FL
28/07 – 01/08
102 €/nighttotal: 408 € (4 )
Chris & Tish Cozy Apartments -1 Bedroom With Queen Size Bed.
1 2
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.
9.9 59 reviews
Winter Park, FL
28/07 – 01/08
367 €/nighttotal: 1468 € (4 )
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
4 2
apartment , Casselberry
This four-bedroom, three-bathroom apartment in Winter Park, approximately 32 kilometres from Universal Studios and International Drive, and 32 kilometres from Disney World, offers a luxurious retreat close to Casselberry. The 300 square metre property, including 100 square metres of outdoor space, boasts a Japandi design, a chef's kitchen, outdoor kitchen with grill, dedicated workspace, Smart TVs, and accommodates up to twelve guests.