Winter Springs vacation rentals

We found 18,163 vacation rentals — enter your dates for availability

Discover a selection of 9 homes and other vacation rentals in Winter Springs that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the amenities you need and want for your stay, which might include WiFi and a washer and dryer, No matter what you're looking for, you'll find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Winter Springs

Showing deals for:Jul 24 - Jul 31

Image gallery for THE CHLOE by EVRH

Living area
9.0 out of 10, Wonderful, (70 reviews)
Wonderful
(70 reviews)

THE CHLOE by EVRH

Altamonte Springs

8% off
Price is $231
$1,614 for 7 nights
All fees included
THE CHLOE by EVRH

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Find out more about Winter Springs

Why visit Winter Springs

  • Family-friendly activities: Enjoy a variety of attractions that cater to visitors of all ages, ensuring fun for the whole family.
  • Outdoor adventures: Explore scenic parks and natural landscapes perfect for hiking, biking, and picnicking.
  • Cultural experiences: Visit local art museums and engage with the vibrant artistic community.
  • Charming neighborhoods: Stroll through nearby Winter Park for delightful dining and shopping experiences.
  • Comfortable accommodations: Choose from a range of vacation rentals, from cozy homes to luxurious villas, for a memorable stay.

Popular types of accommodation in Winter Springs

Discover the perfect getaway in Winter Springs, FL, with a variety of vacation rentals to suit your needs. Whether you prefer a cozy private vacation home, a spacious condo, or a luxurious villa, we have options for every traveler. Enjoy essential amenities like air conditioning and additional rooms for a comfortable stay. Whatever your choice, you're guaranteed a wonderful stay in this charming destination.

  • Houses: The top choice for visitors to Winter Springs, offering spacious accommodations perfect for families or groups.
  • Condos: A popular option for those seeking comfort and convenience, providing amenities and often located near attractions.
  • Villas: These luxurious residences offer a blend of privacy and upscale living, ideal for a relaxing getaway.
  • Apartments: A practical choice for solo travelers or couples, providing a homely feel with essential conveniences.
  • Cottages: Quaint and charming, these cozy spaces are perfect for a romantic escape or a peaceful retreat.**

Top attractions near Winter Springs

Winter Springs, Florida, offers a delightful mix of family-friendly activities and outdoor adventures perfect for a city-themed vacation. Explore urban parks, visit local art museums, and check out nearby medical centers. The attractions cater to travelers seeking a blend of leisure and cultural experiences, ensuring memorable moments for everyone in the family.

  • Boombah-Soldiers Creek Park: This urban park, located 1 mile from Winter Springs, offers a vibrant family-friendly atmosphere with plenty of outdoor activities, including walking trails and sports fields, perfect for a day of fun and relaxation.
  • Wekiwa Springs State Park: Situated 9 miles away, this national park features stunning natural scenery, crystal-clear springs, and diverse wildlife, providing a thrilling adventure for hiking, canoeing, and exploring nature.
  • Deer Run Country Club: Just 3 miles from Winter Springs, this private country club exudes luxury with its beautifully landscaped golf course, upscale dining, and exclusive amenities for a refined experience.

Things to do recommended for couples

For a romantic getaway in Winter Springs, indulge in luxury at Deer Run Country Club, only 3 miles away. Alternatively, enjoy the upscale ambiance at Alaqua or Mayfair Country Club, both located 6 miles from town. Perfect spots for couples seeking an intimate experience.

Things to do recommended for families

Families visiting Winter Springs can enjoy the beautiful trails at the Central Winds Park, perfect for picnics and play. They can also explore the interactive exhibits at the nearby Orlando Science Center, making for an exciting and educational day out for everyone.

Things to do recommended for groups

Explore the scenic trails of the Cross Seminole Trail with your group, or enjoy a fun-filled day at the local parks like Central Winds Park, which offers sports fields and picnic areas perfect for gatherings. Don't miss the vibrant local dining scene for a true taste of Florida.

*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 Springs

When traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winter Springs with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Winter Springs with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, as well as look for suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a smart move.
  • Taking your pets with you to Winter Springs: For many families, a vacation wouldn't be the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that your entire family, including your pets, feels comfortable and at home.
  • Planning for a long term stay visiting Winter Springs: If you're in search of vacation rentals with special offers 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 preferences like a parking spot, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Winter Springs

Winter Springs offers a delightful blend of family-friendly activities and scenic outdoor experiences, making it an ideal vacation spot. Nearby Winter Park boasts charming neighborhoods with vibrant atmospheres, perfect for leisurely strolls and local dining. Explore the area's housing trends and friendly communities while enjoying budget-friendly options. Don't miss the beautiful landscapes and the welcoming vibes of the South Shore region, enhancing your travel experience in this captivating part of Florida.

  • Orlando: Orlando is a bustling metropolis located 12 miles from Winter Springs, renowned for its family-friendly attractions and entertainment options. Visitors flock to this vibrant city for world-famous theme parks like Walt Disney World and Universal Studios, making it a prime destination for thrill-seekers and families alike. Beyond the parks, Orlando boasts a plethora of shopping areas and cultural venues, including art galleries and theaters. With stunning beaches and film studios nearby, Orlando offers a diverse travel experience that caters to all ages and interests.
  • Longwood: Just 2 miles from Winter Springs, Longwood is a charming city perfect for those seeking an outdoor, family-oriented atmosphere. This city features beautiful parks, recreational areas, and golf courses, making it an ideal spot for leisure activities. Longwood is also home to stunning urban parks and is close to national state parks, providing ample opportunities for hiking, picnicking, and enjoying nature. With its friendly community and inviting ambiance, Longwood offers a relaxing getaway with plenty of outdoor adventures.
  • Casselberry: Located 2 miles from Winter Springs, Casselberry is a delightful city that combines family-friendly activities with outdoor experiences. Visitors can explore educational venues, relaxing resorts, and golf courses, catering to a variety of interests. The city is conveniently located near theme parks and features urban parks perfect for outdoor enjoyment. With access to a modern college university, Casselberry also embraces a youthful vibe, making it a great destination for families and those looking to immerse themselves in a lively community.

Best time to go to Winter Springs

If you're planning a trip to Winter Springs, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
February64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighAverage
April72.5°F (22.5°C)Light RainMostly SunnySlightly HighAverage
May77.0°F (25.0°C)Light RainMostly SunnyAverageAverage
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 SunnyAverageSlightly Low
September80.2°F (26.8°C)Light RainMostly SunnySlightly HighSlightly Low
October75.0°F (23.9°C)Light RainMostly SunnySlightly LowSlightly Low
November68.0°F (20.0°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December64.0°F (17.8°C)No Rain (Dry)Mostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming trip? Being flexible with your travel dates can be a smart strategy, as prices often vary. Additionally, booking a longer stay typically 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've got you covered.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you an organized area to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you've saved and booked, categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The beautiful city of Winter Springs awaits you

Enjoy the temples and other features of Winter Springs. This scenic city is known for its baseball games, lake and parks. Universal Orlando Resort and Kia Center are just a couple of the must-sees in the area. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Winter Springs

Are you hoping to find attractions to see while you're in town? Venture out of your vacation home and experience everything that makes Winter Springs a fun spot to vacation. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Universal Orlando Resort (18.4 mi / 29.6 km)
  • Central Florida Zoo & Botanical Gardens (8.9 mi / 14.3 km)
  • Rio Pinar Country Club (12.2 mi / 19.6 km)
  • King's Landing (12.8 mi / 20.6 km)
  • Ventura Country Club (13 mi / 20.9 km)
  • MetroWest Golf Club (16 mi / 25.8 km)

Exploring the natural landscape of Winter Springs

Whether you're an adventurous traveler or just want to take in the scenery, Winter Springs is a great place to get outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Boombah-Soldiers Creek Park (1.5 mi / 2.4 km)
  • Red Bug Lake Park (3.4 mi / 5.5 km)
  • Cranes Roost Park (5.2 mi / 8.4 km)
  • Sanlando Park (5.5 mi / 8.9 km)
  • Lake Jesup (5.7 mi / 9.2 km)
  • Harry P. Leu Gardens (9.4 mi / 15.1 km)

How to get to and around Winter Springs

The nearest airport is in Orlando Sanford Intl. Airport (SFB), located 6.6 mi (10.6 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Orlando Intl. Airport (MCO), which is 18.5 mi (29.8 km) away.

Frequently asked questions

What is the best area to stay in Winter Springs, Florida, United States of America when booking a vacation rental?
When considering a vacation rental in Winter Springs, Florida, the best area to stay in is near the scenic Lake Jesup. This neighborhood offers a serene environment with beautiful views and access to outdoor activities. Nearby, you can explore the lovely Central Winds Park, which features walking trails, sports facilities, and picnic areas, making it a superb spot for families and outdoor enthusiasts alike.

Another appealing area is the charming downtown Winter Springs, where you can enjoy a quaint atmosphere with local shops and eateries. The Winter Springs Town Center often hosts events and has a vibrant community feel, making it an excellent choice for those wanting to immerse themselves in local culture.
How much does it cost to rent a vacation home in Winter Springs?
Prices for vacation rentals in Winter Springs 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winter Springs to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winter Springs vacation house rentals?
You can find great discounts on house rentals in Winter Springs 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.
What is the most popular type of vacation rental accomodation in Winter Springs?
In Winter Springs, vacation houses are the most popular type of accommodation, with several available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor spaces, making them ideal for families or groups looking to relax. Many properties are situated in quiet residential neighborhoods, offering a peaceful environment while still being conveniently located near local parks and recreational areas.
Are there any family house rentals in Winter Springs?
In Winter Springs, Florida, there are several family-friendly house rentals available, making it a great choice for those traveling with children. The neighborhoods in this area offer spacious homes with amenities tailored for families, such as fully equipped kitchens, large living areas, and outdoor spaces where kids can play or enjoy a barbecue.

Visitors can take advantage of nearby parks, like Central Winds Park, which features playgrounds, sports fields, and picnic areas, superb for a day of outdoor fun. Additionally, the proximity to local attractions, including the scenic shores of Lake Jesup, provides opportunities for family outings and nature exploration.
Can I rent a vacation home with a pool or hot tub in Winter Springs?
In Winter Springs, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for those seeking a relaxing getaway. This charming community is located in Central Florida and offers a variety of amenities in its rental properties. Travelers can expect homes with private pools, spacious outdoor areas for lounging, and sometimes even hot tubs for unwinding after a day of exploration. Many rentals also come equipped with full kitchens, allowing for convenient meal preparation, and cozy living spaces for gathering with family and friends.
Can I find long-stay vacation rentals in Winter Springs?
A long-stay vacation rental in Winter Springs is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winter Springs?
In Winter Springs, there are several pet-friendly house rentals available, providing a welcoming environment for travelers with furry companions. Many of these homes come equipped with spacious backyards, great for pets to play, as well as modern amenities such as fully equipped kitchens, comfortable living areas, and sometimes even private pools.

The neighborhood is known for its family-friendly atmosphere, with nearby parks like Central Winds Park and the expansive Tuscawilla Park, both of which offer walking paths and green spaces ideal for leisurely strolls with pets. Additionally, the area features pet-friendly cafes and shops, making it convenient for pet owners to enjoy their stay while accommodating their four-legged friends.
Are there any remote work vacation rentals in Winter Springs?
In Winter Springs, Florida, there are several vacation rentals that cater to remote work needs. Many properties offer essential amenities such as high-speed Wi-Fi, ensuring that you can stay connected while enjoying your stay. Travelers can expect a variety of accommodations, including spacious homes with dedicated workspaces and comfortable living areas, great for balancing work and relaxation.

Additionally, many rentals allow events, providing flexibility for those who may need to host small gatherings. The area is well-suited for remote workers, offering a peaceful environment along with access to local parks and recreational facilities, making it a great choice for a work-from-home getaway. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winter Springs vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winter Springs with parking available—perfect for families or travelers 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 Springs?
In Winter Springs, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals during their stay. Many properties also feature porches or lanais, providing a comfortable outdoor space to relax and enjoy the pleasant Florida weather. Onsite parking is commonly available, making it convenient for guests with vehicles. Additionally, rentals often come with amenities like blenders for preparing smoothies or drinks, and decks or patios that offer a great spot for outdoor dining or leisure activities.
When is the best time to visit Winter Springs for a vacation rental?
September is the most popular time to visit Winter Springs, as the weather remains warm while it's less busy. This month is superb for travelers seeking outdoor activities and opportunities to explore the beautiful parks, scenic trails, and local attractions that characterize this charming Florida town.

During the peak season from February to April, visitors can enjoy mild temperatures ranging from the low 50s to the high 70s Fahrenheit. This is an ideal period for those who appreciate outdoor sightseeing, including visits to the nearby scenic springs and nature parks, where you can enjoy activities like hiking, kayaking, and birdwatching amidst lush landscapes.

For travelers looking for a more budget-friendly option, October presents a wonderful opportunity to experience Winter Springs with fewer tourists. The weather remains pleasant, making it a great time for leisurely strolls or picnics in the parks, while still enjoying the vibrant fall foliage.

Ultimately, your ideal time to book a vacation rental in Winter Springs will depend on whether you prefer the lively option of the peak season or the tranquil charm of the shoulder months, where you can enjoy the natural beauty of the area at a more relaxed pace.
How early should I book a Winter Springs vacation rental?
Book your Winter Springs 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.
What are the top attractions in Winter Springs, Florida, United States of America?
In Winter Springs, visitors can enjoy a variety of attractions that highlight the area's natural beauty and community spirit. The Central Winds Park is a popular spot, offering sports fields, picnic areas, and a playground, making it ideal for families. Nearby, the Winter Springs Town Center features shops, restaurants, and outdoor spaces where locals gather for events and activities.

For those who enjoy nature, the Cross Seminole Trail runs through the area, providing a scenic route for walking, biking, or jogging. The beautiful Lake Jessup, located just a short drive away, offers opportunities for fishing and wildlife observation. The historic downtown area adds charm with its quaint shops and local eateries, reflecting the town's character and inviting atmosphere.
Can I change or cancel my Winter Springs home rental booking on Vrbo?
To find Winter Springs 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winter Springs 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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