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Best Short term and Weekly rentals in Winter Park, FL
9.9 354 reviews
Winter Park, FL
06/28 – 07/18
$94/nighttotal: $1880 (20 )
St. Hemingway Suite
1 1
B&B , Altamonte Springs
This peaceful vacation rental is located near Altamonte Springs, offering easy access to theme parks, beaches, and local attractions. The property has received excellent ratings for its cleanliness, location, and overall experience. This one-bedroom apartment comfortably accommodates two guests and features a private entrance, a bathroom, and access to a large lake. Guests can enjoy a private dock, swimming pool, manicured lawns, and a kitchenette for preparing light meals.
10 17 reviews
Winter Park, FL
09/03 – 09/08
$177/nighttotal: $885 (5 )
Modern Luxury King Suite | Central Orlando + Pool
1 2
apartment , Orlando
This studio apartment in Downtown Orlando is located within a 5-10 minute walk of Lake Eola, performing arts venues, and nightlife, with Universal Studios 15 miles away, Epic Universe 17 miles away, and Walt Disney World 27 miles away. This pet-friendly accommodation accommodates up to 4 guests and features a full kitchen, air conditioning, a swimming pool, a fitness center, and complimentary covered garage parking.
10 5 reviews
Winter Park, FL
06/20 – 06/27
$222/nighttotal: $1554 (7 )
Close To The Action, Peaceful When You Return - 2br In Downtown, Sleeps 6
2 6
apartment , Orlando
This Downtown Orlando condo is located in the Lawsona - Fern Creek neighborhood, less than a 5-minute walk to Lake Eola Park, 5 miles to Amway Center, and 10 miles to Camping World Stadium. This 2-bedroom, 1-bathroom rental sleeps up to 5 guests and includes a full kitchen with a microwave oven and dishwasher, air conditioning, parking, and an on-site washer and dryer.
9.6 190 reviews
Winter Park, FL
08/02 – 08/04
$190/nighttotal: $380 (2 )
Stylish Duplex Walkto Lake Eola Orlando. Sleeps 8
1 6
apartment , Orlando
This two-bedroom, two-bathroom Orlando duplex is located in the Thornton Park neighborhood, a short walk from Lake Eola Park and its Sunday farmers market, and a 20-minute drive from Orlando's theme parks. The 8-guest unit features a fully equipped kitchen, two 55" Roku TVs, two dedicated workspaces, free on-site parking for two vehicles, and an open-concept living area with a fireplace and bar.
9.9 77 reviews
Winter Park, FL
07/21 – 08/04
$112/nighttotal: $1568 (14 )
Nook Haven | Glamping Retreat •Pool • Hot Tub
1 1
glamping , Goldenrod
This campervan, under the offer "Glamping Rv*free Parking *Private Patio*sleeps 5", is situated in a quiet Winter Park cul-de-sac, 7 miles from Downtown Orlando's performing arts venues and 3 miles from Winter Park's Park Avenue. This family-friendly glamping oasis accommodates up to 5 guests with 1 bedroom and 1 bathroom, featuring air conditioning, internet, a kitchenette with a fridge, freezer, and microwave, a private 200 sq ft patio, and access to a shared swimming pool and hot tub.
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.
9.6 8 reviews
Winter Park, FL
06/20 – 06/27
$203/nighttotal: $1421 (7 )
Home In Orlando
3 6
apartment , Azalea Park
This three-bedroom apartment rental in Orlando's Azalea Park neighborhood offers convenient access to Florida Mall, Orlando International Premium Outlets, Universal Orlando Resort, and The Wizarding World of Harry Potter. The 3-bedroom, 2-bathroom unit sleeps six guests and includes a king bed, two queen beds, a fridge, microwave, air conditioning, Wi-Fi, a washer, and parking.
9.6 4 reviews
Winter Park, FL
08/11 – 08/13
$126/nighttotal: $252 (2 )
Orlando Tiny Home Near Kia Center W Free Parking
1 2
apartment , Orlando
This one-bedroom apartment is situated in the Lawsona - Fern Creek neighborhood of Orlando, just minutes from Lake Eola and 20 minutes from Orlando's theme parks. The apartment features a sleek modern design, a fully equipped kitchen with a glass cooktop, microwave, and a large refrigerator with an ice maker, a private porch, and a modern bathroom with an oversized rain shower.
Winter Park, FL
06/17 – 06/23
$67/nighttotal: $402 (6 )
Chic Studio Near Downtown & Theme Parks
1 1
studio , Orlando
This studio apartment in Orlando is located 5.3 miles from Church Street Station and 5.4 miles from the Kia Center, offering convenient access to downtown attractions. This 400 sq ft pet-friendly accommodation sleeps up to 3 guests and features a kitchenette with a microwave, air conditioning, free WiFi, and an on-site garden.
9.1 43 reviews
Winter Park, FL
06/20 – 06/27
$403/nighttotal: $2821 (7 )
New Renovated House Near Everything
1 6
apartment , Eatonville
This stylish apartment is centrally located in Eatonville, offering easy access to the heart of the city. With excellent user and location ratings, this 3-bedroom, 2-bathroom apartment can accommodate up to 5 guests. The apartment boasts a fresh and contemporary look, providing a comfortable and inviting stay. Guests enjoy access to a range of amenities, including free Wi-Fi, a fully equipped kitchen, and a private balcony.
10 2 reviews
Winter Park, FL
09/03 – 09/08
$164/nighttotal: $820 (5 )
The Palm | Stylish Stay Close To Downtown Orlando
1 2
apartment , Orlando
This restored 1959 apartment in Orlando offers a prime location, just 5 minutes from Downtown nightlife, 7 minutes from major concert venues, 18 minutes from Universal Studios, 25 minutes from Walt Disney World, and 20 minutes from the Convention Center, with walking distance to the Mills 50 district and Ivanhoe Village. This 2-bedroom, 1-bathroom condo accommodates up to 6 guests and features a designer kitchen with a fridge, freezer, microwave, and dishwasher, a screened patio with an outdoor TV, a private turf backyard with a fire pit and hammock, an EV charging station, an in-home washer and dryer, and a dedicated coffee bar.
9.9 236 reviews
Winter Park, FL
08/11 – 08/13
$83/nighttotal: $166 (2 )
Private Entrance/bathroom 10 Min From Dt Orlando
1 2
B&B , Eatonville
This cozy Eatonville room with a private bath is conveniently located near Orlando, approximately 10 minutes from downtown, 30 minutes from Orlando International Airport (MCO) and Walt Disney World, and 20 minutes from Universal Studios. This 1-bedroom, 1-bathroom unit sleeps 4, features air conditioning, free internet, parking, a full-size water purifier, and is powered by 100% renewable energy.
Find the Best Family-Friendly Lodgings in Winter Park, FL
Keep the kids entertained with a rental located just steps from Winter Park, FL's top attractions.
10 45 reviews
Winter Park, FL
06/17 – 06/23
$248/nighttotal: $1488 (6 )
Downtown Zen. Perfect Location To Explore Downtown Orl. Private 1 Bedroom House
1 1
apartment , Orlando
This Orlando vacation home is located in Colonialtown South, just a short distance from attractions like The Plaza Theatre and Kia Center. It has received excellent ratings from previous guests. This spacious house features a private pool, a fitness center, and a game room. You'll also find a fully equipped kitchen, a fireplace, and a fenced yard.
Winter Park, FL
09/03 – 09/08
$132/nighttotal: $660 (5 )
76 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests
2 2
apartment , Orlando
This four-bedroom, two-bathroom vacation rental in Ventura Golf Resort, Orlando, is conveniently located 15 minutes from Walt Disney World, 25 minutes from Universal Studios, and 10 minutes from Orlando International Airport. The 820-square-foot condo features a fully equipped kitchen, in-suite laundry, private balcony, and access to resort amenities including a pool, fitness center, and 18-hole golf course; it comfortably sleeps four guests.
9.2 17 reviews
Winter Park, FL
07/03 – 07/31
$128/nighttotal: $3584 (28 )
#1 Rated Neighborhood|.4 Mi. To Advent Hospital
1 2
apartment , Orlando
This College Park bungalow, a 2-bedroom, 1-bathroom house, is located 0.4 miles from AdventHealth Hospital and 0.7 miles from College Park's Main Street, offering easy access to local shops and restaurants. This Orlando vacation rental sleeps four, features a fenced backyard, a separate office, a full kitchen with dishwasher, and includes amenities such as a swimming pool, fitness center, and parking; a minimum 28-day stay is required.
10 2 reviews
Winter Park, FL
08/02 – 08/04
$298/nighttotal: $596 (2 )
Comfortable & Quiet 2br/2ba, Near Park Ave & Rollins, Extended Stays Welcome.
2 6
apartment , Goldenrod
This modern 2-bedroom, 2-bathroom condo is located in Orlando's Goldenrod neighborhood, offering a quiet retreat just minutes from Park Avenue's shops and restaurants, Rollins College, and major attractions like Disney and Universal theme parks. This family-friendly apartment features a fully equipped kitchen, in-unit laundry, air conditioning, a garden, and parking, with a private fenced patio and complimentary breakfast items, snacks, and bottled water for guest convenience.
Best Winter Park, FL lodging with a kitchen
9.4 306 reviews
Winter Park, FL
06/28 – 07/18
$95/nighttotal: $1900 (20 )
Lake Eola View 1 Bedroom Thornton Park
1 1
apartment , Orlando
This Thornton Park condo overlooks Lake Eola, offering proximity to the Dr. Philips Center for the Performing Arts and numerous restaurants and bars in the Thornton Park district. This one-bedroom, one-bathroom unit sleeps two guests and includes a kitchen with a refrigerator, freezer, and microwave, plus parking, air conditioning, and access to Hulu, Netflix, and the AT&T cable app.
9.6 80 reviews
Winter Park, FL
07/21 – 08/04
$92/nighttotal: $1288 (14 )
Luxury Apt + Pool + Bbq + Gym.
1 1
apartment , Orlando
This centrally located Orlando studio apartment is minutes from Downtown Orlando, a short drive from the Orange County Convention Center, Universal Studios Florida, and Walt Disney World. The 1-bedroom unit features a fully equipped kitchen, a living area with a sheepskin sofa and smart TV, sleeps up to 3 guests, and includes high-speed Wi-Fi, a swimming pool, fitness center, and parking.
9.7 27 reviews
Winter Park, FL
06/28 – 07/18
$117/nighttotal: $2340 (20 )
The Emerald, Milk District Gem! Unit 2
1 1
apartment , Orlando
This Milk District rental is conveniently located one mile from Lake Eola and minutes from Downtown Orlando, offering easy access to Universal Studios (25-minute drive) and Disney World (30-40 minute drive). This one-bedroom, one-bathroom house sleeps three guests and features a kitchen with a fridge, freezer, and microwave, plus air conditioning, a garden, on-site parking, and free Wi-Fi; it's pet-friendly with self check-in and a 4/20 friendly policy (outdoor smoking/vaping only).
9.9 73 reviews
Winter Park, FL
08/02 – 08/04
$381/nighttotal: $762 (2 )
Sweet Magnolia, Spacious Downtown 3bd/2.5ba
3 6
apartment , Orlando
This spacious 1650-square-foot historic home is located in Downtown Orlando, offering easy access to various attractions. This three-bedroom, two-and-a-half-bathroom house sleeps six, features a fully equipped kitchen, high-speed internet (350mbps), and a sunroom, perfect for families or groups visiting Orlando.
Frequently Asked Questions about short term rentals in Winter Park, FL
Which top landmarks you shouldn't miss in Winter Park, FL?
Winter Park is full of charming spots! You definitely want to see the iconic Morse Museum of American Art, known for its collection of Louis Comfort Tiffany glass. You should also stroll around the Park Avenue area, filled with boutiques and restaurants, and stop by the Alfond Inn, a beautiful hotel with a stunning art collection.
What are the best short term rentals in Winter Park, FL?
What kind of weather can travelers expect in Winter Park, FL?
Winter Park has a subtropical climate, which means you'll have warm, humid summers and mild winters. Expect temperatures in the 70s and 80s in the summer and 50s and 60s in the winter. Don't forget to pack for rain, as it can be a bit unpredictable throughout the year.
What are the best short term rentals with a pool in Winter Park, FL?
What are the most popular festivals and events in Winter Park, FL?
Winter Park is a hub for events! The Winter Park Sidewalk Art Festival is a huge draw, showcasing the work of local artists. The Winter Park Autumn Art Festival is another popular event, and you can also catch the Winter Park Concours d'Elegance, which features vintage and classic cars.
What are the best short term rentals with a jacuzzi in Winter Park, FL?
Are there any famous stadiums or sports arenas in Winter Park, FL?
While Winter Park doesn't have any major sports stadiums, you can find the Winter Park Racquet Club where you can watch some local tennis matches or even try your hand at the sport.
What are the best short term rentals for families and kids in Winter Park, FL?
What notable natural landmarks are near Winter Park, FL?
Winter Park is close to some beautiful natural spots. The Wekiwa Springs State Park is a great place to go for hiking, kayaking, and swimming. You can also visit the Blue Spring State Park to see manatees in their natural habitat.
What part of Winter Park, FL is ideal for finding lodging?
The Park Avenue area is a great place to stay in Winter Park. It's close to many restaurants, shops, and attractions. If you're looking for a more residential feel, the Baldwin Park neighborhood is also a popular choice.
Destinations nearby
Best Winter Park, FL lodging with laundry available
9.8 614 reviews
Winter Park, FL
07/21 – 08/04
$48/nighttotal: $672 (14 )
Winter Park, Cozy Small Room.
1 1
apartment , Goldenrod
This charming bed and breakfast is situated in a peaceful Winter Park neighborhood, just a short drive from Goldenrod. It boasts excellent ratings for user experience, location, and cleanliness, making it a great choice for travelers seeking a comfortable and convenient stay. The single-bedroom guesthouse offers a queen-size bed, a shared bathroom with amenities, and a private, fenced pool and jacuzzi. Guests can enjoy a cozy, comfortable space with access to a fully equipped kitchen, air conditioning, and free parking.
Winter Park, FL
08/11 – 08/13
$138/nighttotal: $276 (2 )
Trendy 1br Steps To Lake Eola - Thornton Park
1 2
apartment , Orlando
This 1-bedroom condo is situated in Orlando's Thornton Park district, a short walk from Lake Eola and within 1.1 miles of Church Street Station and Kia Center. This air-conditioned unit accommodates up to 3 guests with free WiFi and private parking, featuring a full kitchen and two living rooms for added space.
9.0 3 reviews
Winter Park, FL
08/11 – 08/13
$141/nighttotal: $282 (2 )
The Pineapple Express
1 2
apartment , Orlando
The Pineapple Express apartment offers convenient access to downtown Orlando attractions, located 3.1 miles from the Kia Center and Church Street Station, and 4.3 miles from Camping World Stadium. This 1190 square foot, 1-bedroom unit accommodates up to 9 guests and features a fully equipped kitchen, complimentary WiFi, and free on-site parking, with Orlando International Airport 10 miles away.
9.6 128 reviews
Winter Park, FL
07/03 – 07/10
$126/nighttotal: $882 (7 )
Sleeps 3, Winter Park & Downtown
1 2
apartment , Fairview Shores
This Winter Park apartment rental is centrally located, minutes from Park Avenue's restaurants and shops, Rollins College, and a 25-minute drive from Orlando's major theme parks. The newly renovated one-bedroom, one-bathroom unit sleeps four guests and features a fully stocked kitchen, high-speed Wi-Fi, free parking for two vehicles, and a fully remodeled bathroom.
Neighborhoods and points of interest in Winter Park, FL
Best Winter Park, FL lodging with air conditioning
9.6 20 reviews
Winter Park, FL
08/02 – 08/04
$208/nighttotal: $416 (2 )
Dog-friendly Apt W/ Fenced Yard In Winter Park
2 6
apartment , Goldenrod
This studio apartment is located in Goldenrod, Winter Park, offering proximity to Walt Disney World, Orlando International Airport, and downtown Winter Park, with beaches approximately 45 miles away. This 650 sq ft dwelling accommodates up to 6 guests, featuring a kitchenette with essential appliances, central air conditioning, free WiFi, and a small fenced yard perfect for pets, with nearby attractions including the Winter Park Tennis Center and Dubsdread Golf Course.
9.9 113 reviews
Winter Park, FL
07/03 – 07/10
$152/nighttotal: $1064 (7 )
Cottage Retreat In The City
1 2
cottage , Orlando
This charming cottage is located in College Park, a historic neighborhood in Orlando, just a short drive from Universal Studios, Walt Disney World, and Downtown Orlando. The cottage consistently receives excellent ratings for location, cleanliness, and overall guest experience. The cozy cottage has one bedroom and one bathroom, comfortably accommodating up to two guests. Enjoy a private outdoor space with a large front porch, a fully equipped kitchen, a modern HD TV, and free Wi-Fi.
Winter Park, FL
06/28 – 07/18
$106/nighttotal: $2120 (20 )
Lake Eola View 1 Bedroom Thornton Park
1 1
apartment , Orlando
This Orlando condo is located in Thornton Park, offering a Lake Eola view and situated 0.7 miles from the city center, a 17-minute walk to Church Street Station, and 1.1 miles from the Kia Center. This one-bedroom, one-bathroom apartment accommodates up to three guests and features complimentary WiFi, private parking, a fully equipped kitchen with an oven and microwave, and air conditioning for your convenience.
9.5 34 reviews
Winter Park, FL
06/20 – 06/27
$193/nighttotal: $1351 (7 )
Downtown Orlando Sports House & Free Parking
1 6
apartment , Orlando
This three-bedroom, one-bathroom house is located in downtown Orlando, within walking distance of the Amway Center and a short drive from Exploria Stadium. This 3-bedroom home sleeps up to 10 guests and features a fully equipped kitchen, high-speed Wi-Fi, on-site parking, and hand-painted murals throughout; pets are welcome.