Winter Park vacation rentals

We found 1,497 vacation rentals — enter your dates for availability

Discover a selection of 69 homes, 27 apartments, and other vacation rentals in Winter Park that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you expect for your stay, which might include a garden and WiFi. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Winter Park

Showing deals for:Nov 14 - Nov 21

Image gallery for 4/2.5 Resort-like lake front saltwater pool home

Miscellaneous
10 out of 10 rating
Exceptional
(27 reviews)

4/2.5 Resort-like lake front saltwater pool home

Orlando, FL

5% off
Price is CA $402
CA $3,687 total
includes taxes & fees
4/2.5 Resort-like lake front saltwater pool home

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Winter Park

Find out more about Winter Park

Why visit Winter Park

  1. Charming neighbourhoods: Winter Park features picturesque streets and inviting communities perfect for leisurely exploration.
  2. Cultural experiences: The city boasts vibrant art museums and galleries that showcase local and international talents.
  3. Scenic parks and lakes: Enjoy outdoor activities in beautifully maintained parks and tranquil lakes that offer stunning views.
  4. Family-friendly attractions: There are numerous activities suitable for families, ensuring fun for visitors of all ages.
  5. Diverse accommodation options: From cozy villas to vacation rentals, there’s a perfect place to stay for every traveller.

Popular types of accommodation in Winter Park

Discover a variety of vacation rentals in Winter Park, perfect for your getaway! Whether you're seeking a private vacation home, a cozy villa, or a convenient condo, we have options to suit every traveller's needs. With a focus on transparency and savings, our platform connects you to the best vacation rentals in Winter Park, including those near Winter Park Resort. Explore your ideal home away from home today!

  • Houses: The top choice for visitors seeking a spacious and comfortable stay, ideal for families or groups looking to enjoy a home-like atmosphere in Winter Park.
  • Villas: A luxurious option for those wanting upscale amenities and beautiful surroundings, perfect for a relaxing getaway.
  • Condos: A convenient choice that combines comfort with accessibility, often located near popular attractions.
  • Apartments: An excellent option for solo travellers or couples seeking a cozy and functional space to unwind.
  • Cottages: Charming and quaint, these offer a picturesque retreat for those wanting a serene escape.**

Top attractions in Winter Park

Winter Park, Florida, is an ideal destination for families and those seeking entertainment or cultural experiences. Visitors can enjoy urban parks, picturesque lakes, and vibrant art museums that provide a mix of outdoor activities and family-friendly fun. Whether you’re travelling solo or with loved ones, Winter Park offers a delightful blend of attractions that will make your vacation unforgettable.

  1. Orlando Science Center: This interactive science museum, located 4.8km from Winter Park, offers family-friendly exhibits that inspire curiosity and exploration, making it a fun and educational experience for all ages.
  2. Dr. Phillips Center for the Performing Arts: Situated 8.0km from Winter Park, this vibrant arts centre hosts a variety of performances, showcasing the best in culture and entertainment, perfect for arts enthusiasts.
  3. Full Sail University: Nestled within Winter Park, this historic university is renowned for its innovative programs in entertainment and media, providing a unique glimpse into creative education.

Things to do recommended for couples

For a romantic getaway in Winter Park, indulge in tennis at the luxurious Winter Park Tennis Center. Enjoy an entertaining evening at The Social, just 8.0km away, or savour a delightful dinner at Pirate's Dinner Adventure, 14.8km from Winter Park, perfect for a charming night out.

Things to do recommended for families

Families visiting Winter Park can enjoy a day of excitement at the Kia Center for some sports action, splash around at Universal’s Volcano Bay waterpark for thrilling adventures, or relax at the Alfond Swimming Pool for family-friendly outdoor fun.

Things to do recommended for groups

Explore the vibrant Winter Park Village for shopping and entertainment, or immerse yourselves in culture at the nearby Orlando Shakespeare Theater and Enzian Theater, both offering delightful performances just 3.2km away. It's a perfect mix of family-friendly activities and romantic outings for your group!

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

If you're planning a trip with a group, family, or pets, or if you're interested in extended stays, it's important to prioritize your preferences when filtering your options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winter Park with a group: Take into account how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Park with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Winter Park: For many families, a trip isn’t truly fulfilling without their furry companions by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations 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 searching for vacation rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like parking, 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 activities and vibrant city life, making it an ideal vacation destination. Explore its charming neighbourhoods, enjoy scenic views, and indulge in local art. With a range of accommodations, this city provides the perfect getaway for everyone. Don't miss the chance to experience winter sports and the warm hospitality of friendly locals, ensuring a memorable trip for all visitors.

  • Orlando: Located a mere 8.0km from Winter Park, Orlando is a vibrant city famed for its attractions and entertainment options. Visitors flock to this bustling metropolis for family fun, business events, and world-class entertainment. A highlight of Orlando is its array of theme parks, including the iconic Walt Disney World and Universal Studios, which offer unforgettable experiences for all ages. Beyond the parks, explore the thriving arts scene and shopping districts, or unwind in one of the luxurious resorts. Orlando's convenient access to film studios and event conference venues makes it an ideal destination for both leisure and business travellers.
  • Baldwin Park: Nestled around Winter Park, Baldwin Park is a charming neighbourhood that combines family-friendly activities with a lively urban experience. This picturesque area features lovely parks, scenic lakes, and a variety of shops and restaurants. Visitors can enjoy leisure activities such as cycling or strolling along the waterfront. With its proximity to modern colleges and film studios, Baldwin Park offers a unique blend of education and entertainment. The community atmosphere and vibrant local events make it a great spot for exploring with family and friends.
  • Goldenrod: Located near Winter Park, Goldenrod is a bustling neighbourhood that caters to families, business travellers, and city explorers alike. This area boasts a rich array of shopping centres, from malls to local boutiques, making it a shopping haven. Goldenrod is also home to notable educational institutions, including modern and historic colleges. The nearby theme parks provide thrilling adventures, while the local dining scene offers diverse options for every palate. Goldenrod’s welcoming community vibe and convenient access to attractions make it a must-visit during your stay.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 SunnyAverageAverage
May77.0°F (25.0°C)Light RainMostly SunnySlightly LowAverage
June81.0°F (27.2°C)Light RainMostly SunnyAverageSlightly High
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 simple

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can be beneficial, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make informed choices for a fantastic getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a convenient platform to plan new getaways, refine your existing travel arrangements, or keep track of your reservations. The properties you’ve saved or booked are thoughtfully categorized into Potential, Upcoming, or Current Trips for your ease of access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The lively area of Winter Park awaits your stay

Enjoy the live music and other features of Winter Park. Renowned for its university setting, shopping and gardens, this city welcomes all visitors. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Winter Park

Are you searching for attractions to visit in the area? Venture out of your vacation home and experience everything that makes Winter Park a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Universal Studios Florida (11.6 mi / 18.7 km)
  • Universal Orlando Resort (11.7 mi / 18.9 km)
  • Walt Disney World® Resort (19.4 mi / 31.3 km)
  • The Wizarding World of Harry Potter™ (11.5 mi / 18.5 km)
  • Universal’s Islands of Adventure (12 mi / 19.3 km)
  • Universal’s Volcano Bay (12.5 mi / 20.2 km)

Exploring the natural landscape of Winter Park

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Winter Park is a great spot to appreciate mother nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Harry P. Leu Gardens (2.3 mi / 3.8 km)
  • Lake Eola (4.4 mi / 7 km)
  • Lake Eola Park (4.4 mi / 7.1 km)
  • Red Bug Lake Park (4.6 mi / 7.4 km)
  • Cranes Roost Park (5.3 mi / 8.5 km)
  • Tinker Field (5.8 mi / 9.3 km)

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?
When considering a vacation rental in Winter Park, Florida, a popular area to stay is the charming neighbourhood of Park Avenue. This vibrant area is renowned for its picturesque tree-lined streets, boutique shops, and a delightful selection of cafes and restaurants, making it a great spot for those who enjoy a lively atmosphere. Park Avenue is also home to the beautiful Central Park, which offers lovely walking paths and scenic views, ideal for leisurely strolls or picnics.

Another excellent option is the Rollins College area, where the stunning campus is set against the backdrop of Lake Virginia. This neighbourhood features a mix of historic homes and modern amenities, providing a tranquil setting just a short distance from the bustling Park Avenue. Visitors can explore the nearby Morse Museum of American Art, which houses an impressive collection of Tiffany glass, making it a must-visit for art enthusiasts.
How much does it cost to rent a vacation home in Winter Park?
Prices for vacation rentals in Winter Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Park to more spacious homes.
Are there any discounts for Winter Park vacation house rentals?
You can find great discounts on house rentals in Winter Park on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Winter Park ski resort rentals?
For the best ski resort rentals near Winter Park, Florida, travellers should focus on the area surrounding the Winter Park Resort itself. The town of Winter Park offers a variety of vacation rentals, including condo-style accommodations and charming cabins that are great for groups or families. Many of these properties come equipped with essential amenities such as kitchens or kitchenettes, allowing for easy meal preparation after a day on the slopes.

In addition to proximity to the ski lifts, some rentals feature cosy fireplaces and outdoor spaces, which provide a great setting to unwind and enjoy the stunning mountain views. The nearby Fraser area also has options for those seeking a quieter stay, with traditional mountain lodges and modern townhomes available.
What is the most popular type of vacation rental accomodation in Winter Park?
In Winter Park, vacation houses are the most prevalent type of accommodation, with around 60 available throughout the area. These spacious properties are typically located in serene neighbourhoods, providing ample room for families or groups, and often include amenities such as fully equipped kitchens, multiple bedrooms, and private outdoor spaces for relaxation. Additionally, there are approximately 23 apartments scattered around the town, offering a more compact option with similar comforts like kitchen facilities and cosy living areas, making them ideal for couples or small families. For those seeking a more luxurious experience, several villas and condos are also accessible, featuring upscale amenities and sometimes private pools or hot tubs.
Are there any family house rentals in Winter Park?
In Winter Park, Florida, there are numerous family-friendly house rentals available, with around 46 options to choose from. This charming area is known for its outdoor recreational activities and vibrant community atmosphere, making it an excellent choice for groups looking to enjoy a fun-filled getaway.

Properties in this locale often feature spacious living areas, full kitchens where families can prepare meals together, and cozy outdoor spaces for relaxation. Many homes come equipped with amenities like Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay for all guests.
Can I rent a vacation home with a pool or hot tub in Winter Park?
In Winter Park, Florida, there are plenty of vacation homes available for rent that come with pools or hot tubs, with around 34 options to choose from. This charming area is renowned for its outdoor activities and proximity to beautiful natural landscapes. Many of these properties are situated in family-friendly neighbourhoods and often feature amenities like private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, making them great for relaxation after a day of exploring or enjoying the local attractions. Find your rental in Winter Park with a pool or a hot tub.
Can I find long-stay vacation rentals in Winter Park?
A long-stay vacation rental in Winter Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winter Park?
In Winter Park, there are numerous pet-friendly house rentals available, with a variety of options to suit different preferences and group sizes. Many of these vacation homes offer amenities such as fully equipped kitchens, spacious living areas, and outdoor patios, superb for enjoying the pleasant Florida weather.

The area is known for its beautiful natural surroundings, including parks and lakes, where pets can enjoy the outdoors. For instance, the nearby Winter Park Chain of Lakes provides ample opportunities for walking and recreational activities with pets. Additionally, the local parks often have walking trails and open spaces, making it convenient for pet owners to explore the area with their furry companions.
Are there any remote work vacation rentals in Winter Park?
In Winter Park, Florida, there are numerous remote work vacation rentals available, with around 78 options to choose from. This charming area is known for its beautiful scenery and outdoor activities, making it an appealing destination for those looking to balance work and leisure. Many of the properties come equipped with essential amenities such as Wi-Fi, dedicated workspaces including desks and chairs, and some even offer additional features like safe storage for valuables and computer monitors. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winter Park with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winter Park?
In Winter Park, popular vacation rental amenities include complimentary Wi-Fi, fully equipped kitchens, and essential appliances such as refrigerators and microwaves. Travellers can expect to find cookware, dishware, and utensils provided, making it convenient for those who prefer to prepare their own meals during their stay.
When is the best time to visit Winter Park for a vacation rental?
February is the most popular time to visit Winter Park, Florida, making it a prime choice for those seeking a vacation rental. This period falls within the peak season, which spans from January to March, attracting visitors eager to enjoy the temperate climate while engaging in outdoor activities. With average temperatures hovering around 20°C, February offers a delightful escape for those looking to bask in the sunshine and explore the scenic beauty of the area.

During this time, the vibrant atmosphere of Winter Park is palpable, with a variety of events and activities that cater to different interests. From leisurely strolls along the picturesque Park Avenue, lined with unique shops and cafes, to enjoying the scenic lakes and gardens, there is no shortage of options for sightseeing and relaxation.

For those considering a more budget-friendly option, May presents a lovely opportunity to visit. Although this month falls in the low season, it offers warm weather and fewer crowds, making it ideal for enjoying the local parks and outdoor spaces without the hustle and bustle of peak tourism. The natural beauty remains, and you can appreciate the tranquillity of Winter Park at a more leisurely pace.
How early should I book a Winter Park vacation rental?
Book your Winter Park vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Winter Park home rental booking on Vrbo?
To find Winter Park vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winter Park vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

Explore destinations around Winter Park

People also search for

Vacation rentals with pool in Kissimmee
Standard Link for Kissimmee
Orlando Townhomes
Standard Link for Orlando
Kissimmee Vacation Homes
Standard Link for Kissimmee
Celebration Cottages
Standard Link for Celebration
Kissimmee Resorts
Standard Link for Kissimmee
Pet-friendly vacation rentals in Kissimmee
Standard Link for Kissimmee
Kissimmee Villas
Standard Link for Kissimmee
Orlando Villas
Standard Link for Orlando
Orlando Cottages
Standard Link for Orlando
Beach vacation rentals in Orlando
Standard Link for Orlando
Family-friendly vacation rentals in Orlando
Standard Link for Orlando
Lake Buena Vista Resorts
Standard Link for Lake Buena Vista
Orlando Apartments
Standard Link for Orlando
Vacation rentals with pool in Orlando
Standard Link for Orlando
Lake Buena Vista Apartments
Standard Link for Lake Buena Vista
Lake Buena Vista Villas
Standard Link for Lake Buena Vista
Orlando Cabin Rentals
Standard Link for Orlando
Orlando Guest Houses
Standard Link for Orlando
Kissimmee Townhomes
Standard Link for Kissimmee
Orlando Resorts
Standard Link for Orlando
Kissimmee B&B
Standard Link for Kissimmee
Pet-friendly vacation rentals in Orlando
Standard Link for Orlando
Kissimmee Cottages
Standard Link for Kissimmee
Orlando Vacation Homes
Standard Link for Orlando

More Vacation Rentals ideas

Lake Buena Vista Vacation Rentals
Standard Link for Lake Buena Vista
Maitland Vacation Rentals
Standard Link for Maitland
Windermere Vacation Rentals
Standard Link for Windermere
Orlando Vacation Rentals
Standard Link for Orlando
Celebration Vacation Rentals
Standard Link for Celebration
Kissimmee Vacation Rentals
Standard Link for Kissimmee