Winter Park vacation rentals

We found 1,624 vacation rentals — enter your dates for availability

Welcome to Winter Park, where charming streets lined with unique boutiques and vibrant cafes invite exploration amidst lush parks and serene lakes. This picturesque destination offers families and groups a wealth of cultural experiences, from art galleries to historical museums, ensuring memorable adventures for all ages. With a diverse selection of vacation rentals, including cozy homes and spacious villas, you can enjoy the comforts and amenities of a home away from home while creating lasting memories together.

Holiday rentals with weekly discounts - Winter Park

Showing deals for:Dec 11 - Dec 18

Exterior
Dining
Living area
Private kitchen
Wonderful
(21 reviews)

Orlando 4 BR Home Centrally Located on Dead End St

Orlando

9% off
$267
$1,871 for 7 nights
All fees included
Orlando 4 BR Home Centrally Located on Dead End St
Full Kitchen
Living room with sky windows for natural sunlight
Front yard
Back Yard
Exceptional
(6 reviews)

Orlando 1 Acre 4 BD Home Central Near Universal

Orlando

13% off
$254
$1,776 for 7 nights
All fees included
Orlando 1 Acre 4 BD Home Central Near Universal
Living area
Dining
Room
Private kitchen
Exceptional
(7 reviews)

Lake Getaway to Orlando Magic!

Apopka

18% off
$526
$3,683 for 7 nights
All fees included
Lake Getaway to Orlando Magic!
Exterior
Private kitchen
Living area
Living area
Exceptional
(11 reviews)

2 miles from UCF and 1 mile from Oviedo On the Park 2-bedroom house

Oviedo

9% off
$200
$1,401 for 7 nights
All fees included
2 miles from UCF and 1 mile from Oviedo On the Park 2-bedroom house
Room
Exterior
Private kitchen
Private kitchen
Exceptional
(30 reviews)

SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging

Orlando

5% off
$144
$1,006 for 7 nights
All fees included
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
Dining
Living area
Living/dining room
Guest room
Exceptional
(6 reviews)

Royal Blue 2 Bedroom Condo in Orlando Central.

Orlando

8% off
$163
$1,139 for 7 nights
All fees included
Royal Blue 2 Bedroom Condo in Orlando Central.
Exterior
Interior
Interior
Interior
Exceptional
(11 reviews)

“Downtown Orlando Comfy House”

Orlando

9% off
$199
$1,392 for 7 nights
All fees included
“Downtown Orlando Comfy House”
family room directly off the pool patio
full size kitchen to utilize everything included
Covered spa/hot tub, patio grill available, view to fenced bach yard
master bedroom ensuite, split plan
Exceptional
(12 reviews)

Tropical Pool & Spa Home, 3/2, Near Disney, Universal, Sea World, Beaches

Altamonte Springs

8% off
$233
$1,634 for 7 nights
All fees included
Tropical Pool & Spa Home, 3/2, Near Disney, Universal, Sea World, Beaches
Room
Living area
Interior
Living area
Exceptional
(6 reviews)

A comfortable home close to the city, yet tucked away from the noise.

Orlando

7% off
$159
$1,116 for 7 nights
All fees included
A comfortable home close to the city, yet tucked away from the noise.
Pool
Private kitchen
Terrace/patio
Dining
Exceptional
(6 reviews)

The Orlando Oasis with Private Pool

Orlando

9% off
$362
$2,532 for 7 nights
All fees included
The Orlando Oasis with Private Pool
Private kitchen
Exterior detail
Living area
Room
Exceptional
(27 reviews)

Winter Park Oasis

Winter Park

9% off
$183
$1,280 for 7 nights
All fees included
Winter Park Oasis
Dining
Living area
Room
Private kitchen
Exceptional
(8 reviews)

Cozy Private Apartment 10 minutes from Downtown Orlando

Orlando

7% off
$80
$563 for 7 nights
All fees included
Cozy Private Apartment 10 minutes from Downtown Orlando
Terrace/patio
Interior
Living area
Room
Exceptional
(6 reviews)

Downtown Orlando “Birdhouse”

Orlando

8% off
$199
$1,392 for 7 nights
All fees included
Downtown Orlando “Birdhouse”
Private kitchen
Living area
Room
Interior
Exceptional
(16 reviews)

Treehouse Lake Davis - 1BR Private Modern Home with Balcony Downtown

Orlando

9% off
$167
$1,170 for 7 nights
All fees included
Treehouse Lake Davis - 1BR Private Modern Home with Balcony Downtown
Room
Private kitchen
Dining
Living area
Exceptional
(9 reviews)

Charming Walkable Attic Bungalow near Lake Eola with Full Kitchen

Orlando

9% off
$165
$1,157 for 7 nights
All fees included
Charming Walkable Attic Bungalow near Lake Eola with Full Kitchen
Room
Outdoor dining
Interior
Interior
Exceptional
(17 reviews)

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

Orlando

8% off
$264
$1,847 for 7 nights
All fees included
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
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Find out more about Winter Park

Why visit Winter Park

  • Scenic Urban Parks: Winter Park boasts beautiful parks perfect for family outings and outdoor activities.
  • Picturesque Lakes: The area features stunning lakes ideal for leisurely walks, picnics, and water activities.
  • Vibrant Art Museums: Explore the local art scene through diverse museums and galleries showcasing unique collections.
  • Charming Neighborhoods: Wander through delightful neighborhoods filled with historic homes and local shops.
  • Diverse Accommodation Options: Choose from spacious vacation homes, villas, or cozy condos to suit your stay.

Popular types of accommodation in Winter Park

Winter Park offers an array of vacation rentals to suit every traveler's needs, including houses, villas, and condos. Whether you're seeking spacious house rentals for family gatherings or cozy condos for a romantic getaway, there's something for everyone. With convenient parking spaces and numerous options for a memorable stay, our Winter Park vacation rentals provide the perfect base to explore this stunning destination.

  • Houses: The top choice for travelers in Winter Park, these homes offer a spacious and comfortable stay for families and groups.
  • Villas: A close second, villas provide luxurious accommodations with stunning views and amenities for a relaxing getaway.
  • Condos: Ideal for shorter stays, condos offer modern conveniences and often come with access to shared facilities.
  • Apartments: A practical option, apartments give you the flexibility of home-cooked meals in a cozy setting.
  • Cottages: These charming retreats are perfect for a quaint and peaceful escape, surrounded by nature.**

Top attractions in and around Winter Park

Winter Park, Florida, offers a delightful vacation for families and entertainment seekers alike. Explore its urban parks, picturesque lakes, and vibrant art museums, perfect for outdoor adventures and cultural experiences. Whether you're traveling with family or friends, Winter Park promises a memorable getaway filled with local attractions and enriching activities to enjoy.

  • Orlando Science Center: Located 3 miles from Winter Park, this interactive science museum offers engaging exhibits and hands-on activities, perfect for families and curious minds alike.
  • Rollins College: Nestled in Winter Park, this modern college campus boasts beautiful architecture and vibrant city vibes, making it a great spot to explore the local culture.
  • Full Sail University: Also in Winter Park, this historic university is known for its creative programs and artistic community, offering a unique glimpse into the world of entertainment and media.

Things to do recommended for couples

For a romantic getaway in Winter Park, enjoy live music at The Social, or indulge in luxury at Rio Pinar Country Club. Don't miss the enchanting experience at Pirate's Dinner Adventure, where you can savor a delightful meal in a lively atmosphere perfect for couples.

Things to do recommended for families

Your family will love the excitement of Lil 500 Go-Karts, just 3 miles from Winter Park, and the refreshing Alfond Swimming Pool right in town. For sports enthusiasts, the Kia Center, located 5 miles away, offers a lively atmosphere perfect for a fun family outing.

Things to do recommended for groups

Group travelers in Winter Park can enjoy shopping and entertainment at Winter Park Village, experience a cultural night at The Plaza Theatre just 4 miles away, and play a round of golf at Dubsdread Golf Course located 3 miles from the city, perfect for outdoor enthusiasts.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winter Park

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, it's important to prioritize your needs when filtering your options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winter Park with a group: Think about how many bedrooms you'll require, as well as additional features like a full kitchen or outdoor area for group activities. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Park with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Winter Park: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, consider exploring Vrbo listings that are pet-friendly. Many of these properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter Park: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the perfect spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Winter Park

Winter Park, Florida, offers a delightful blend of family-friendly attractions and vibrant urban experiences. Explore charming neighborhoods filled with picturesque homes, enjoy the scenic parks perfect for family outings, and indulge in local dining. Nearby cities also provide additional entertainment options, making it an ideal destination for a memorable vacation. Whether you're seeking a mountain getaway or a relaxing park visit, Winter Park is a fantastic choice for travelers of all ages.

  • Orlando: As a bustling metropolis, Orlando is a premier destination for family-friendly entertainment and outdoor experiences. Located just a short drive from Winter Park, visitors can explore world-renowned theme parks, such as Walt Disney World and Universal Studios, which offer thrilling rides and immersive attractions. The city is also home to vibrant shopping areas and arts centers, making it a great spot for leisure activities. Don't miss the beautiful Lake Eola Park, perfect for a leisurely stroll or a paddleboat ride, and be sure to check out the local dining scene for a taste of Orlando’s diverse culinary offerings.
  • Baldwin Park: Nestled around Winter Park, Baldwin Park is a charming neighborhood known for its family-oriented atmosphere and city vibes. This planned community features scenic lakes and parks, providing a peaceful escape for outdoor enthusiasts. Enjoy shopping at boutique stores or indulge in a meal at one of the many restaurants lining the streets. Baldwin Park is also close to educational institutions and film studios, making it an exciting area to explore for both leisure and learning. The community hosts various events throughout the year, adding to its lively charm.
  • Goldenrod: Located near Winter Park, Goldenrod is a vibrant neighborhood that offers a blend of family, city, and business experiences. The area is known for its convenient shopping centers and educational facilities, catering to both residents and visitors. Explore local shops or unwind at the parks in the area, which are perfect for family outings. Goldenrod’s proximity to modern and historic colleges adds a unique cultural aspect, while its closeness to theme parks ensures there's always something exciting to do. Whether you're here for business or leisure, Goldenrod has something for everyone.

Best time to go to Winter Park

If you're planning a trip to Winter Park, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like May, August and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
February64.0°F (17.8°C)Light RainMostly SunnySlightly HighSlightly Low
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
April72.5°F (22.5°C)Light RainMostly SunnyAverageSlightly High
May77.0°F (25.0°C)Light RainMostly SunnySlightly LowAverage
June81.0°F (27.2°C)Light RainMostly SunnyAverageAverage
July82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnySlightly LowAverage
September80.2°F (26.8°C)Light RainMostly SunnyAverageSlightly Low
October75.0°F (23.9°C)Light RainMostly SunnyAverageSlightly Low
November68.2°F (20.1°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.0°F (17.8°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can really help, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient space for you to plan new trips, keep your travel arrangements on track, or manage your existing bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Winter Park is warm enough to make your cares melt away

If the word "winter" conjures images of icy winds and smiling snowmen, think again. This city is where smart travelers flee the harshest winter climates for something a little more summery. Known for its chain of tree-lined lakes and colorful gardens, Winter Park has long been a retreat for families, older folks, and couples enjoying romantic honeymoons. These lucky visitors benefit from a surprisingly chic array of restaurants and classy boutiques, plus impressive art museums and historic homes. You can count on your Winter Park vacation rental being close to worldly attractions, but suffused with a get-away-from-it-all vibe.

A little city with big art, long history, and grand gardens

For a suburban city spread over a mere 10 square miles, Winter Park has an awfully swanky collection of cultural, historical, and natural attractions. Its Charles Hosmer Morse Museum of American Art is world-famous for its collection of Louis Comfort Tiffany pieces. The Hannibal Square Heritage Center is dedicated to the African Americans who lived and worked in the area in the 19th century. Plus, no matter where your Winter Park vacation rental lies, it'll be close to a botanical garden. The Mead Botanical Garden on Lake Sue and the Kraft Azalea Gardens on Lake Maitland are standouts.

Enjoy the sunny scene on foot, on wheels, or on the water

The easiest way to enjoy Winter Park is simply to step outside and start walking toward Park Avenue, a prime destination for excellent restaurants, upscale shopping, and cocktail bars with outdoor seating. Tired of walking? Keep the sightseeing going with a scenic boat tour through the lakes, or take a bike tour of historic homes and buildings. Of course, you can always head 30 minutes south to Walt Disney World if that's what the family is clamoring for, but Winter Park has a way of making anything other than its quaint southern charm seem unnecessary.

Enjoy the winter of your content in Winter Park

What's in a name? In this case, plenty. Maybe it's called Winter Park because you should park yourself here all winter. Temperatures range from the high 50s to the 70s on most days from November through February, and although prices are at a premium, the sunny skies might be worth it. Spring and fall are also special, especially if you're looking for a bargain on a Winter Park vacation rental. Just remember that rainy weather (and occasional hurricanes) can hit from June to November. Bring your rain gear and listen to local meteorologists.

Tropical trees and feathered friends abound in Winter Park

Winter Park's warm, watery climate is perfect for the oaks and moss-draped camphor trees that make you feel like you're on the edge of a wetland wilderness, even while strolling through the middle of town. Paddle a kayak, or take a boat tour through the city's many lakes and admire the banana trees as you keep an eye out for black anhingas and purple martins. This is an ideal destination for bird watchers. The Mead Botanical Garden has reported sightings of barred owls, Cooper's hawk, and the rare red-headed woodpecker.

Traveling to and around Winter Park

The nearest airport is in Orlando Intl. Airport (MCO), located 11.8 mi (19 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Orlando Sanford Intl. Airport (SFB), which is 13.4 mi (21.6 km) away.

If you prefer train travel, the main station is Winter Park Station.

Frequently asked questions

What is the best area to stay in Winter Park when booking a vacation rental?
Among the more popular locations to book a vacation home in Winter Park is Goldenrod. Discover your dream stay on Vrbo and experience this area like a local.
What is the most popular type of vacation rental accommodation in Winter Park?
Based on our research, apartments are the most sought-after vacation rental type in Winter Park. But as you'd expect, everyone's idea of an epic trip isn't going to be the same. Vrbo has vacation homes in a variety of shapes and sizes, and we'll help you to find the perfect fit.
How much does it cost to rent a vacation rental in Winter Park?
The average price for a vacation rental in Winter Park depends on a number of factors, such as season, length of stay and property type. Whether you're looking for a sprawling villa with a pool or a quaint cabin just enough for two, just enter your travel dates to see stays with exceptional value.
How much does it cost to rent a beach house in Winter Park?
When you travel and the size and style of the property will influence the cost of your beachside vacation rental. Put in your Winter Park travel dates to see all your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to pick the features and amenities you want in your vacation home.
Are there pet-friendly vacation rentals in Winter Park?
Pack a bone and a squeezy toy for the pup in your life because Winter Park has 91 properties that throw out the welcome mat to pets. Let your four-legged pal enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Winter Park?
Pack your swimsuit and inflatable lounger, because there are 46 houses with a private pool in Winter Park. Kick back at one of these sought-after vacation rentals and make every day a pool day. Simply enter your dates into Vrbo, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Winter Park?
An electric car charging station, a garden and a nearby waterfront head the list of most popular rental amenities in Winter Park. Whether you plan to go alone, with your other half or as a family, Vrbo can help you find a vacation rental that fits your style with all the features you'll enjoy.
Are there large group vacation rentals in Winter Park?
Winter Park has five vacation homes that can host 10 or more guests. These stays come with enough space to enjoy good times with your nearest and dearest.
Are there vacation rentals in Winter Park that welcome kids?
With 89 family-friendly vacation properties to pick from in Winter Park, now is a great time to introduce your kids to the thrills of travel. Check our "Properties good for families" filter to find stays loaded with amenities ideal for vacationing families, such as living rooms, patios, entertainment areas and bunk beds.
What are the top attractions for families in Winter Park?
There's a ton of awesome things to do and see with the family in Winter Park, including:
  • Winter Park Country Club
  • Crealde School of Art
  • Winter Park Village
Are there one-bedroom vacation rentals in Winter Park?
You can pick from 26 one-bedroom rentals in Winter Park. Whether you're searching for a cozy cottage or an upmarket condo, our one-bedroom rentals are great if you don't require a lot of space. One of the main perks of having your own digs? You'll never need to share your trip with strangers.
Can I find two-bedroom vacation rentals in Winter Park?
Take your pick of 33 two-bedroom rentals in Winter Park. Give the kids the second room or fill it with a couple of your best buddies. There's space for whoever's fortunate enough to be joining your journey.
Are there vacation rentals with WiFi in Winter Park?
Winter Park has 63 vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to catching up on social media, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Winter Park?
Winter Park has 89 vacation rentals where you'll be able to relax in air-conditioned comfort. To find a stay on Vrbo with this amenity, enter your preferred travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Winter Park?
The minimum age is normally 16, 18 or 21. It can vary from one property to another on Vrbo, so look at the rules of your preferred Winter Park vacation home before you book.
How long can I rent a vacation rental in Winter Park for?
The amount of time you can stay in a Winter Park vacation rental for is down to each property. Just tap in your preferred travel dates to find options offering longer term stays. They have all the things you need to make your extended break more comfortable and convenient, like kitchens and air conditioning. Some Vrbo vacation rentals may also offer weekly or monthly discounted prices, so you can hang around longer for less.
Does Vrbo offer discounts for vacation homes in Winter Park?
Weekend retreat or a well-deserved long vacation, Vrbo has some exclusive deals and discounted options in Winter Park to suit your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what's recently been added with one of our newly listed homes. Whatever it is you're after, you'll find the ideal place to stay — without breaking the bank.

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