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Winter Springs vacation rentals

We found 17,847 vacation rentals — enter your dates for availability

Discover a selection of 8 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:Nov 14 - Nov 21
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Find out more about Winter Springs

Find out more about Winter Springs

Why visit Winter Springs

  1. Outdoor Adventures: Winter Springs boasts scenic parks and lakes ideal for hiking, biking, and family picnics.
  2. Family-Friendly Attractions: The area offers various activities and attractions perfect for all ages, ensuring fun for the whole family.
  3. Cultural Vibrancy: Experience a lively atmosphere filled with art, culture, and friendly locals.
  4. Diverse Accommodation Options: Choose from private vacation homes, condos, and villas that cater to different budgets and preferences.
  5. Charming Community Spirit: Enjoy the welcoming vibe of Winter Springs, making it an inviting destination to create lasting memories.

Popular types of accommodation in Winter Springs

If you're exploring Winter Springs for your next getaway, you'll find a variety of accommodation options to suit your needs. The most popular choices include houses, condos, and villas. Whether you're searching for winter springs house rentals, top winter springs house rentals, or apartments for rent, our platform ensures you have access to transparent information, great savings, and peace of mind for your vacation.

  • Houses: The top choice for visitors, these spacious homes offer a perfect retreat for families, friends, or couples seeking a relaxing getaway in Winter Springs.
  • Condos: Popular among travellers, condos provide modern amenities and a convenient location for exploring the area.
  • Villas: A luxurious option, villas offer comfort and privacy, ideal for those looking to indulge during their stay.
  • Apartments: A practical choice, apartments cater to those who prefer a home-like atmosphere while enjoying their vacation.
  • Cottages: Quaint and charming, cottages are perfect for a cozy, intimate escape in Winter Springs.**

Top attractions in Winter Springs

Winter Springs, Florida, is perfect for outdoor enthusiasts and families seeking a city-themed getaway. Visitors can explore a variety of attractions, including urban parks, scenic lakes, and modern college campuses. The area's points of interest cater to those looking for enjoyable outdoor activities and family-friendly experiences, ensuring a memorable vacation in this charming locale.

  1. University of Central Florida: Experience a vibrant campus atmosphere with modern architecture and diverse student life. This institution offers a glimpse into contemporary education and innovation, located 14.5km from Winter Springs.
  2. Boombah-Soldiers Creek Park: A lively urban park perfect for families, featuring outdoor recreational activities, playgrounds, and walking trails, just 1.6km away from Winter Springs. Enjoy the lush greenery and community vibe.
  3. Full Sail University: Immerse yourself in the rich cultural environment of this historic institution, known for its focus on arts and entertainment. Located 11.3km from Winter Springs, it's a hub of creativity and inspiration.

Things to do recommended for couples

For a romantic getaway in Winter Springs, consider a luxurious day at Deer Run Country Club, enjoy live music at The Social, or have some fun at Congo River Golf in Altamonte Springs. Each experience offers a unique blend of relaxation and adventure for couples.

Things to do recommended for families

Your family will love the Seminole County Sports Complex for relaxation, the thrill of racing at Lil 500 Go-Karts, and the fun at Bounce House. Each location offers a unique experience, making your visit to Winter Springs both memorable and enjoyable for everyone.

Things to do recommended for groups

Explore the vibrant Altamonte Mall for shopping and entertainment, hit the Tuscawilla Golf Course for an outdoor sports day, and enjoy the local flavours at the Lake Mary Farmer's Market nearby. These activities ensure a memorable group experience in Winter Springs!

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

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

  • Traveling to Winter Springs with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Winter Springs with young kids: Traveling with young children can present its own set of challenges. It’s essential to prioritize their comfort and safety, and to look for age-appropriate amenities, like a private swimming pool. Additionally, it's wise to take into account your distance from family-friendly attractions.
  • Taking your pets with you to Winter Springs: For many families, a vacation isn’t truly fulfilling without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. The majority of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winter Springs: If you're seeking vacation rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search as well.

Where to stay in Winter Springs

Winter Springs, Florida, offers a delightful blend of outdoor activities and family-friendly attractions. Explore the scenic parks and nearby neighbourhoods, where you'll find charming homes and friendly locals. Enjoy the vibrant atmosphere filled with art and culture, perfect for budget-conscious travellers. With its hot summers and inviting community spirit, Winter Springs is an ideal destination for those looking to experience the best of Florida's charm while creating lasting memories with loved ones.

  • Orlando: Located approximately 19.3km from Winter Springs, Orlando is a vibrant metropolis known for its family-friendly atmosphere and entertainment options. Visitors flock to this city for its renowned theme parks, including Walt Disney World and Universal Studios, which promise unforgettable experiences for all ages. Beyond the thrills of the parks, Orlando boasts extensive shopping areas, diverse dining options, and cultural attractions such as the Orlando Museum of Art. The city blends urban excitement with beautiful outdoor spaces, making it a must-visit destination for any traveller.
  • Longwood: Just 3.2km from Winter Springs, Longwood is a charming city that offers a delightful mix of outdoor activities and family-oriented experiences. This area is home to several recreational parks and golf courses, ideal for those looking to enjoy nature and sports. Longwood’s proximity to local attractions, including a national state park and urban parks, makes it perfect for leisurely strolls or family picnics. The welcoming community and serene environment provide a pleasant escape from the hustle and bustle of larger cities.
  • Casselberry: Also located 3.2km from Winter Springs, Casselberry is a vibrant city that caters to families and anyone seeking a lively urban experience. The city features various educational venues and shopping mall centres, perfect for a day of retail therapy or learning. Casselberry is conveniently close to popular attractions like theme parks and a modern college university, making it an ideal spot for both relaxation and exploration. Enjoy the local parks and recreational areas, which provide ample opportunities for outdoor fun.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your adventures, allowing you to create new trips, resume your previous ones, or easily manage your travel arrangements. You can conveniently view your saved or booked properties, which are organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/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. Kia Center and Orlando International Premium Outlets 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:

  • Timacuan Golf Club (5.4 mi / 8.7 km)
  • Central Florida Zoo & Botanical Gardens (8.9 mi / 14.3 km)
  • Dubsdread Golf Course (9.4 mi / 15.1 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)

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)
  • Greenwood Lakes Park (3.1 mi / 5 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)

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 most popular type of vacation rental accommodation in Winter Springs?
The most desirable types of vacation rentals in Winter Springs are houses. Ready for more choices? Vrbo offers a variety of options to match the diverse needs of our guests, so you'll see vacation properties in all shapes and sizes. The ideal home away from home is waiting for you — snap up yours today.
How much does it cost to rent a vacation rental in Winter Springs?
The average price for a vacation home in Winter Springs is determined by a number of factors, including length of stay, season and property type. Whether you're dreaming about a sprawling villa with room to move around or a cozy cottage for you and your other half, just enter your dates of travel to view stays with unbeatable value.
How much does it cost to rent a beach house in Winter Springs?
When you travel and the style and size of the property will determine the cost of your beachside stay. Enter your Winter Springs travel dates to view your options on Vrbo. Can't live without a hot tub? Use the filters to select the amenities and features you need.
Are there pet-friendly vacation rentals in Winter Springs?
With nine vacation rentals that allow pets, your furry companion can join in the fun on your Winter Springs break. Use our filter tool to browse our pet-friendly vacation rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Winter Springs?
Mark the "pool" box in our handy filter tool and pick from eight houses with private pools in Winter Springs on Vrbo. Ball games, gentle soak or noodle joust? Free time is up to you when your Vrbo vacation home comes with its own pool.
What are popular rental amenities in Winter Springs?
When it comes to rental amenities that people are on the lookout for in Winter Springs, a barbecue grill, a fireplace and a swimming pool rank the highest. With Vrbo vacation rentals, you'll have options to match your style and taste, whether you're going away with relatives, friends or even pets.
Are there large group vacation rentals in Winter Springs?
Take your pick of three Vrbo vacation rentals in Winter Springs that can host a group of five or more guests. You'll get all the privacy and room you need to chill out with your loved ones — and no one else.
Are there vacation rentals in Winter Springs that welcome kids?
With nine family-friendly vacation rentals available in Winter Springs, now is the perfect time to introduce the kids to the thrills of travel. Simply check our "Properties good for families" filter to find stays packed with amenities perfect for families on the move, like kitchens, patios, entertainment units and bunk beds.
What are the top attractions for families in Winter Springs?
Keep your kids busy at these popular family-friendly attractions in Winter Springs:

  • Central Florida Zoo & Botanical Gardens
  • Sanford Museum
  • Hannibal Square Heritage Center

Are there one-bedroom vacation rentals in Winter Springs?
Yes, there are four one-bedroom properties in Winter Springs to pick from. A one-bedroom vacation rental is a wonderful choice if it's just you and your partner or if you're traveling on your own. Toss in more privacy, space and convenience than a standard hotel, and you're sure to have an unforgettable break.
Can I find two-bedroom vacation rentals in Winter Springs?
Winter Springs has two two-bedroom properties for you to select from. Go for a vacation home with all the comfort and privacy you need at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Winter Springs?
Winter Springs has seven vacation rentals with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to updating your social media, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Winter Springs?
Choose from nine vacation homes with air conditioning in Winter Springs offering that gentle, cool breeze and extra touch of comfort. Just enter your chosen travel dates and then make use of our filters to locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Winter Springs?
The minimum age permitted can differ between properties on Vrbo, so double-check the rules of the vacation rental in Winter Springs you're considering. But typically, it's 16, 18 or 21.
How long can I rent a vacation rental in Winter Springs for?
It's really down to the Winter Springs property. To view a list of options offering extended stays, just enter your dates and number of guests into the Vrbo search page. Enjoy having the entire property to yourself, as well as amenities such as a full kitchen, air conditioning and outdoor spaces where your little ones can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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