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319 Lodgings in Winter Park, FL
10 258 reviews
Winter Park, FL
06/17 – 06/23
$133/nighttotal: $798 (6 )
The Sacred Space Downtown Orlando Milk District
1 1
house , Orlando
This Orlando studio apartment is located in the Milk District, approximately one mile from Lake Eola and a short drive from Downtown Orlando, Universal Studios (25 minutes), and Walt Disney World (30-40 minutes). The unit offers self check-in, a queen-size bed, a kitchenette with complimentary snacks and alkaline water, a private patio, and access to a fitness center and parking; it sleeps two guests and features hypoallergenic bedding and a whole-house water filtration system.
9.9 73 reviews
Winter Park, FL
07/03 – 07/10
$114/nighttotal: $798 (7 )
Tinyhouse On The Edge Of Orlando + Winter Park
1 2
house , Orlando
The Tiny House Orlando, a private guest house, is situated in a peaceful residential area of Orlando, a short walk from the main house, with proximity to local restaurants (distance unspecified). This studio-style rental offers a queen-sized bed, an air mattress for extra guests (total capacity 3), a full kitchen with fridge, microwave, stove, and coffee maker, a private bathroom, and a private backyard entrance.
9.8 37 reviews
Winter Park, FL
09/03 – 09/08
$261/nighttotal: $1305 (5 )
3bd In Winter Park, 10 Min Park Ave/rollins, Pets
1 2
apartment , Winter Park
This three-bedroom Winter Park home offers convenient proximity to AdventHealth Winter Park (2 minutes), Rollins College and Park Avenue (8 minutes), and Winter Park Village (12 minutes). This pet-friendly house sleeps six guests and features a fully equipped kitchen with stainless steel appliances, a garden, fitness center, and parking; nearby attractions include UCF (20 minutes) and Universal Studios (30 minutes).
9.6 101 reviews
Winter Park, FL
07/03 – 07/31
$61/nighttotal: $1708 (28 )
Camper Near Theme Parks, Airport, Major Highways
1 2
cabin , Azalea Park
The Antonio D'camper is located in Celebration, Florida, just a short drive from Walt Disney World, Universal Studios, and SeaWorld, making it an ideal base for exploring the area's attractions. The campervan has received excellent ratings for cleanliness, location, and user experience. The spacious motorhome features two bedrooms, a full bathroom, and a fully equipped kitchen, comfortably accommodating up to five guests. The Antonio D'camper offers amenities like air conditioning, a private garden, and convenient delivery to campgrounds within 60 miles of Celebration, including Disney Fort Wilderness Resort.
9.6 41 reviews
Winter Park, FL
06/28 – 07/18
$162/nighttotal: $3240 (20 )
Charming Winter Park 3 Bedroom Villa With Pool
1 1
house , Casselberry
This East Winter Park villa, near Semoran Boulevard (SR 436), provides easy access to Casselberry, Maitland, Altamonte Springs, and Oviedo, with proximity to Winter Park Hospital and major roadways. The three-bedroom, two-bathroom house sleeps six, features a remodeled kitchen with modern appliances, a community pool, and on-site parking for two cars, and is fully furnished.
9.4 16 reviews
Winter Park, FL
10/10 – 10/21
$142/nighttotal: $1562 (11 )
Alluring 2bd/2ba In East Orlando.
2 4
apartment , Orlando
This two-bedroom, two-bathroom Orlando vacation home is conveniently located near Ventura Country Club, with Rio Pinar Country Club and The Plaza Theatre within 6 miles and Camping World Stadium under 9 miles away. The smoke-free property features a fully equipped kitchen, private patio, swimming pool, fitness center, and accommodates up to four guests, offering easy access to WiFi and housekeeping upon request.
8.7 6 reviews
Winter Park, FL
06/28 – 07/18
$82/nighttotal: $1640 (20 )
Botanical Tranquility
1 1
apartment , Casselberry
This Casselberry apartment rental is conveniently located approximately 11-15 miles from Orlando Sanford International Airport and within a 12-20 mile radius of attractions like the Addition Financial Arena and Camping World Stadium. The one-bedroom, one-bathroom unit sleeps three guests and features a private pool, free Wi-Fi, private parking, a fully equipped kitchen, and an outdoor dining area.
10 1 review
Winter Park, FL
06/19 – 06/29
$150/nighttotal: $1500 (10 )
Mid Term Rental 2 Bedroom Retreat Steps To Lake Eola Thornton Park
2 1
apartment , Orlando
This 2-bedroom condo is located in Orlando's Thornton Park district, a short walk from Lake Eola and 17 minutes on foot to Church Street Station, placing it within 1.1 miles of the Kia Center and 2.4 miles from Camping World Stadium. This 850 square foot residence accommodates up to 7 guests with 2 bedrooms, 2 living rooms, air conditioning, a fully equipped kitchen with a dishwasher and oven, and free private parking and Wifi.
9.8 213 reviews
Winter Park, FL
08/11 – 08/13
$109/nighttotal: $218 (2 )
The Lake House
1 2
apartment , Winter Park
This Winter Park apartment rental is conveniently located in a quiet residential area, a short walk from Starbucks and Panera Bread, and a 4-minute drive from Publix, Walgreens, and Sprouts, with Downtown Winter Park and Park Avenue a 10-minute drive away. This 370-square-foot unit features one bedroom, one bathroom, sleeps four guests, and includes a well-equipped kitchen, Roku TV, Wi-Fi, and a private entrance backing onto a lake.
9.5 54 reviews
Winter Park, FL
08/02 – 08/04
$260/nighttotal: $520 (2 )
3 Br Near Downtown| Hotub, Pool, Gazebo | Sleeps 7
1 6
apartment , Orlando
This Orlando vacation home is near Ivanhoe Village and Mills districts, minutes from I-4, Dubsdread Golf Course, AdventHealth, and downtown Orlando. The three-bedroom, two-bathroom house sleeps eight, features a private backyard with a fire pit and gazebo, a "cowboy pool," and offers keyless entry, high-speed Wi-Fi, and streaming services.
9.2 30 reviews
Winter Park, FL
06/20 – 06/27
$201/nighttotal: $1407 (7 )
Relaxing 3 Bedroom Home With Free Parking & Wi-fi
1 6
apartment , Fairview Shores
This Fairview Shores apartment rental is conveniently located near I-4, providing easy access to the Orlando Science Center (5 miles away) and beaches (45 minutes away). The three-bedroom, two-bathroom unit sleeps six guests comfortably, boasting a family-friendly layout, a Jacuzzi, and a private garden, plus convenient amenities like a dishwasher, microwave, and parking.
Winter Park, FL
06/20 – 06/27
$163/nighttotal: $1141 (7 )
Tiny Home W Outdoor Kitchen & Free Wi Fi
3 6
house , Fairview Shores
This three-bedroom house, ideal for families or groups, is located in Orlando, near Fairview Shores, approximately 3 miles from Downtown Orlando, 3.4 miles from Church Street Station, and 4.5 miles from Camping World Stadium. This 1,000-square-foot home features a fully equipped kitchen, a mother-in-law suite, a private entrance, free Wi-Fi, and can comfortably accommodate up to 11 guests.
Top-Rated Family Lodgings in Winter Park, FL
These family-friendly lodgings in Winter Park, FL offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.
9.9 226 reviews
Winter Park, FL
07/03 – 07/31
$263/nighttotal: $7364 (28 )
Large, Beautiful, Very Comfortable One Bedroom On Small Lake
1 2
apartment , Orlando
This family-friendly vacation home is located near downtown Orlando, just a mile from Lake Eola Park and the Orlando Regional Medical Center. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This 1-bedroom, 1-bathroom rental offers 500 square feet of living space, accommodating up to 2 guests. Amenities include a swimming pool, jacuzzi, sauna, spa, fitness center, tennis court, and a fully equipped kitchen, providing a relaxing and convenient experience.
9.6 19 reviews
Winter Park, FL
06/28 – 07/18
$1498/nighttotal: $29960 (20 )
Renovated Luxury 6000 Sqft Mansion In Downtown Orlando Sleep 14 Near Theme Parks
6 1
apartment , Orlando
This Orlando vacation home boasts a central location, a 15-minute walk from Lake Eola and the Dr. Phillips Center for the Performing Arts, and under 3 miles from Camping World Stadium and the Amway Center. This 6,000-square-foot house features six bedrooms, five bathrooms, sleeps fourteen guests, and includes a private pool, spa, game room, and on-site water park.
10 17 reviews
Winter Park, FL
06/17 – 06/23
$297/nighttotal: $1782 (6 )
New! Spacious Designer 2-bed/2.5-bath Townhome Near Downtown Orlando
2 1
apartment , Orlando
This Lancaster Park vacation home is conveniently located near Orlando Regional Medical Center (1.3 miles) and the Kia of Orlando dealership (2.6 miles), offering easy access to healthcare and shopping. This 1,380-square-foot house features two bedrooms, three bathrooms, sleeps six guests, and includes a fully equipped kitchen, free WiFi, a patio, and an on-site playground.
9.9 72 reviews
Winter Park, FL
07/21 – 08/04
$267/nighttotal: $3738 (14 )
Orlando Tropical Oasis
1 1
apartment , Casselberry
This four-bedroom home in Maitland, Florida, is conveniently located about 30 minutes to an hour from both Orlando's theme parks and the beach. The property has earned excellent ratings for its location, cleanliness, and overall user experience. This spacious rental sleeps up to 8 guests and is perfect for families or groups of friends. The apartment offers a private backyard, a screened-in patio, a fully equipped kitchen, air conditioning, Wi-Fi, and a swimming pool.
Best Winter Park, FL lodging with a pool
Among the 319 accommodations in Winter Park, FL, here are the 4 best ones with a pool
9.8 197 reviews
Winter Park, FL
07/03 – 07/31
$306/nighttotal: $8568 (28 )
Lake House Pets Allowed
2 2
apartment , Orlando
This family-friendly vacation rental is located near downtown Orlando, within a mile of Lake Eola and its park, and within three miles of Camping World Stadium. This property has received excellent ratings for location, cleanliness, and overall experience. This two-bedroom, two-bathroom home comfortably accommodates four guests. The house features a full kitchen, a swimming pool, a jacuzzi, a sauna, a spa, a fitness center, a tennis court, and a garden, offering a variety of amenities and activities for relaxation and entertainment.
9.0 128 reviews
Winter Park, FL
10/05 – 10/14
$518/nighttotal: $4662 (9 )
Century Millenia
2 4
apartment , Orlando
This Florida Center apartment rental is conveniently located less than 1.2 miles from Mall at Millenia and Orlando International Premium Outlets, and within 3 miles of Universal Orlando Resort and Universal CityWalk. The unit offers free Wi-Fi, in-unit laundry, a swimming pool, and concierge service, providing easy access to major attractions and all the comforts of home.
9.9 97 reviews
Winter Park, FL
06/20 – 06/27
$585/nighttotal: $4095 (7 )
* Beautiful Lakehouse With Pool And Movie Theater*
1 6
apartment , Casselberry
This Casselberry vacation rental is conveniently located within walking distance of the Casselberry Golf Course and driving range, offering easy access to all of Orlando's attractions, including Downtown Orlando, theme parks, the springs, Cocoa/Daytona beaches, and Orlando & Sanford Airports. The apartment has earned excellent ratings for its user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay. The spacious home features five bedrooms and two bathrooms, comfortably accommodating up to 16 guests. Enjoy a private screened-in pool, lakefront beach area, water sports equipment, a movie theater room, a modern coffee bar, an outdoor shower, and HD TVs in every room.
9.4 3 reviews
Winter Park, FL
06/20 – 06/27
$184/nighttotal: $1288 (7 )
Quiet And Safe Neighborhood Come To This Great Place With Lots Of Room For Relax
2 6
apartment , Winter Park
This Winter Park rental is a 12-minute drive to the Kia Center and 22 minutes to the Florida Mall, offering convenient access to entertainment and shopping. This 850-square-foot apartment accommodates up to six guests with two bedrooms and two bathrooms, featuring a full kitchen, air conditioning, complimentary Wi-Fi, and access to a communal pool and garden.
Frequently Asked Questions about accommodations in Winter Park, FL
What are the top attractions and must-see sites in Winter Park, FL?
Winter Park is known for its beautiful parks and gardens, like the scenic Rollins College, the charming Mead Garden, and the stunning Kraft Azalea Garden. You can also visit the iconic Winter Park Scenic Boat Tour, which offers breathtaking views of the city's canals and waterways. And don't miss the charming shops and restaurants along Park Avenue, the heart of Winter Park.
What are the best accommodations in Winter Park, FL?
Which cultural festivals and seasonal events should visitors attend in Winter Park, FL?
The Winter Park Sidewalk Art Festival is a must-see, showcasing local artists and their work. The annual Winter Park Autumn Art Festival is another popular event, featuring art, music, and food. For a festive experience, visit the Winter Park Christmas in the Park, a magical event with lights, music, and Santa Claus.
What are the best accommodations with a pool in Winter Park, FL?
What are the most convenient modes of transportation within Winter Park, FL?
Winter Park is very walkable, especially in the downtown area. You can also rent a bike or use the SunRail, a commuter rail system that connects Winter Park to Orlando. If you prefer to drive, parking is available throughout the city, but be prepared for traffic during peak hours.
What are the best accommodations with a jacuzzi in Winter Park, FL?
What outdoor activities and adventures are popular in and around Winter Park, FL?
Winter Park is a great place for outdoor enthusiasts. You can enjoy kayaking or paddleboarding on Lake Maitland, go for a hike in the Wekiwa Springs State Park, or play a round of golf at one of the many golf courses in the area. For a unique experience, visit the Albin Polasek Museum & Sculpture Gardens, featuring beautiful sculptures and gardens.
What are the best accommodations for families and kids in Winter Park, FL?
What types of accommodations are available in Winter Park, FL?
You'll find a variety of accommodations in Winter Park, from cozy bed and breakfasts to luxurious hotels. There are also vacation rentals available, offering more space and privacy. Consider staying near Park Avenue for easy access to shops, restaurants, and attractions.
What are the best pet friendly accommodations in Winter Park, FL?
The best time to visit Winter Park is during the spring and fall, when the weather is pleasant and the crowds are smaller. The summer months can be hot and humid, but the city offers plenty of indoor activities. Winter is a great time to enjoy the holidays and the beautiful Christmas lights.
What are the best accommodations with parking in Winter Park, FL?
What local dishes and culinary experiences are a must-try in Winter Park, FL?
Winter Park has a vibrant culinary scene. Be sure to try the fresh seafood at The Wine Room, the delicious Italian cuisine at Prato, or the innovative dishes at The Ravenous Pig. Don't forget to sample the local craft beers at the Winter Park Brewing Company.
In which part of Winter Park, FL should you consider renting accommodation?
For easy access to shops, restaurants, and attractions, consider staying near Park Avenue. If you prefer a quieter setting, the areas around Lake Maitland or the Kraft Azalea Garden offer peaceful accommodations. For those who want to be close to the action, the downtown area provides a vibrant atmosphere.
Destinations nearby
Best Winter Park, FL accommodation with a garden
9.9 451 reviews
Winter Park, FL
08/02 – 08/04
$256/nighttotal: $512 (2 )
Winter Park Pearl 6 Min Drive To Historic Park Ave
1 6
apartment , Casselberry
Casselberry Cottage is a charming 3-bedroom, 1-bathroom cottage located in a quiet Winter Park neighborhood, just a 5-minute drive from the shops and restaurants of Park Avenue. The cottage has recently been remodeled and features a full kitchen with rustic butcher block counters and Zwilling J.A. Henckels knives, three 50-inch 4k smart TVs, and a private backyard with a charcoal grill. The cottage has received excellent ratings for its location, cleanliness, and user experience, and can accommodate up to 4 guests.
9.9 194 reviews
Winter Park, FL
08/02 – 08/04
$380/nighttotal: $760 (2 )
Stylish Newly Updated Home In Winter Park
1 6
apartment , Fairview Shores
This Fairview Shores apartment offers convenient access to I-4, placing Universal Studios, International Drive, and Disney World within a 20-40 minute drive. Sleeping up to 10 guests, this two-bathroom rental boasts a fully equipped kitchen with modern appliances, a 65" Samsung smart TV, and a large backyard with a fire pit; nearby restaurants are a short walk away.
Winter Park, FL
06/20 – 06/27
$184/nighttotal: $1288 (7 )
Close To The Action, Peaceful When You Return
2 6
house , Orlando
This Orlando house is centrally located, offering proximity to downtown attractions like Church Street Station (1.1 miles) and Kia Center (1.3 miles), with easy access to major theme parks. This 1000 square foot vacation home accommodates up to 11 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen, free WiFi, and a garden.
9.9 61 reviews
Winter Park, FL
07/21 – 08/04
$120/nighttotal: $1680 (14 )
Fern Park Retreat
1 1
apartment , Maitland
This renovated 1958 guest house is located in Fern Park, just a short distance from the SunRail train station, offering easy access to Winter Park and downtown Orlando. The two-bedroom, one-bathroom home features a fully equipped kitchen, a fenced backyard, and a laundry room, perfect for a comfortable and relaxing stay for up to two guests.
Neighborhoods and points of interest in Winter Park, FL
Best Winter Park, FL accommodation with a kitchen
9.7 185 reviews
Winter Park, FL
09/03 – 09/08
$111/nighttotal: $555 (5 )
Cozy Guest House Close To Downtown Orlando
1 2
house , Fairview Shores
This Winter Park guesthouse offers convenient access to Downtown Orlando and Downtown Winter Park (under 10 minutes), major theme parks (15-30 minutes), and beaches (within an hour). The one-bedroom rental features a queen bed, queen sleeper sofa, full kitchen with fridge and microwave, air conditioning, parking, and accommodates up to three guests, with nearby restaurants and supermarkets within walking distance.
9.8 34 reviews
Winter Park, FL
06/28 – 07/18
$112/nighttotal: $2240 (20 )
Sleeps 2 | Lake Eola |Downtown Orlando | Oasis
1 1
apartment , Orlando
This 1-bedroom guest suite is located in the historic Lake Eola Heights neighborhood of Orlando, a 2-minute walk to Lake Eola Park and within easy reach of downtown Orlando's dining, shopping, and the Dr. Phillips Center for the Arts. This second-floor apartment accommodates up to 2 guests and features a fully equipped kitchen, air conditioning, and a garden, with the surrounding area being highly walkable and bike-friendly for local exploration.
9.5 94 reviews
Winter Park, FL
06/20 – 06/27
$376/nighttotal: $2632 (7 )
Orlando Area 5/2 Pool Disney Universal Daytona
5 6
apartment , Altamonte Springs
This Altamonte Springs rental is located a 15-minute drive from Orlando and a short distance from popular attractions like Disney World, Universal Studios, and Epcot. The property boasts excellent user, location, and cleanliness ratings. This 5-bedroom, 2-bathroom home comfortably sleeps up to 16 guests and includes a private pool, a large fenced yard with a charcoal grill, a professional pool table, a regulation-size ping pong table, a fussball table, a domino table, a fully equipped kitchen, high-speed internet, a washer and dryer, and themed bedrooms.
9.8 128 reviews
Winter Park, FL
06/20 – 06/27
$264/nighttotal: $1848 (7 )
Cheerful 3 Bedroom With A Spacious Shaded Yard
1 6
apartment , Goldenrod
This mid-century home is located in Goldenrod, just a short drive from downtown Orlando, Park Ave, and UCF, making it a convenient base for exploring the area. The property consistently receives excellent ratings for its cleanliness, location, and overall experience. This spacious house has three bedrooms and two bathrooms, comfortably accommodating up to 16 guests. Enjoy modern amenities like a full kitchen, washer and dryer, air conditioning, and a private yard perfect for outdoor gatherings.