Leesburg vacation rentals

We found 1,468 vacation rentals — enter your dates for availability

Discover a selection of 35 homes and other vacation rentals in Leesburg that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the best amenities for spending time at your home away from home, including parking and a TV. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Leesburg

Showing deals for:Jul 25 - Aug 1
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Find out more about Leesburg

Find out more about Leesburg

Why visit Leesburg

  1. Outdoor Activities: Leesburg is perfect for nature lovers, with numerous parks, lakes, and state parks for hiking, fishing, and picnicking.
  2. Charming Community: Experience a friendly atmosphere filled with local culture, palm trees, and vibrant community events.
  3. Family-Friendly Attractions: Enjoy various family-oriented activities that cater to all ages, making it ideal for memorable vacations.
  4. Proximity to Orlando: Just a short drive away, Orlando offers exciting excursions and attractions for additional fun.
  5. Diverse Accommodations: Choose from cozy vacation homes, inviting cottages, or luxurious villas to suit your preferences.

Popular types of accommodation in Leesburg

Discover the perfect getaway in Leesburg with our diverse selection of vacation rentals. Whether you're looking for cozy houses, charming cottages, or convenient apartments, we have something to suit every traveler's needs. Explore options like guest houses, resorts in Williamsburg, and beautiful villas in Leesburg. With our focus on transparency and savings, you can find the ideal accommodation for your next adventure.

  • Houses: The top choice among travelers, these spacious homes offer a comfortable and personalized stay for families and groups.
  • Cottages: A delightful option, cottages provide a quaint and cozy atmosphere, perfect for a romantic getaway or a peaceful retreat.
  • Apartments: Ideal for solo travelers or couples, apartments offer convenience and easy access to local attractions.
  • Villas: These luxurious accommodations provide ample space and upscale amenities for an indulgent experience.
  • Cabins: A rustic option for nature enthusiasts, cabins allow you to immerse yourself in the great outdoors.**

Top attractions in Leesburg

Leesburg, Florida, is a fantastic destination for outdoor enthusiasts and families alike, offering stunning scenery and a variety of attractions. Visitors can explore local parks, lakes, and state parks, perfect for outdoor activities and cultural experiences. Don't miss the chance to immerse yourself in the natural beauty and vibrant community that Leesburg has to offer during your vacation.

  1. Venetian Gardens: A beautiful park located within Leesburg, Venetian Gardens offers a family-friendly atmosphere with lush landscapes, walking trails, and serene lakes. It's perfect for a peaceful outdoor retreat and eco-friendly activities.
  2. The Villages Market Square: Situated 9 miles from Leesburg, this vibrant modern square boasts city vibes with a variety of shops, restaurants, and entertainment options. Enjoy live music and events in a lively social atmosphere.
  3. Lake Griffin State Park: Located 3 miles from Leesburg, this national state park is a haven for adventure seekers. Explore scenic trails, fishing spots, and beautiful lake views, ideal for outdoor enthusiasts.

Things to do recommended for couples

For a romantic getaway in Leesburg, indulge in the luxury of Continental Country Club, savor a meal at Cane Garden Country Club, or enjoy live music at the Orange Blossom Opry. Each experience offers a unique blend of charm and ambiance perfect for couples.

Things to do recommended for families

Families can unwind at Gilbert Park, a serene recreational area 14 miles from Leesburg, or enjoy the amenities at the Lake Sumter Sports Complex right in town. Don't miss Marsh Memorial Park, located 12 miles away, perfect for relaxation and fun activities together.

Things to do recommended for groups

Groups visiting Leesburg can experience the vibrant atmosphere at Spanish Springs Town Square for shopping, enjoy family-friendly entertainment at ViaPort Florida, and tee off at the Plantation Golf Club for a fun outdoor sports experience.

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

When traveling with a group, family, or pets, or if you're considering longer stays, it’s essential to prioritize your search effectively. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Leesburg with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search on Vrbo to include all of these options and more.
  • Traveling to Leesburg with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Leesburg: For many families, a vacation wouldn’t be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Leesburg: If you're in search of vacation rentals offering discounts for month-long stays, 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 amenities like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Leesburg

Discover the charm of Leesburg, Florida, where family-friendly outings meet stunning scenery. Explore the heart of Leesburg, adorned with palm trees and vibrant local culture. Just a short drive away, the Orlando area offers exciting excursions and attractions. With its relaxing atmosphere and welcoming community, Leesburg is the perfect destination for outdoor adventures and memorable family vacations. Experience the beauty of Florida in this delightful town!

  • The Villages: Located 11 miles from Leesburg, The Villages is a vibrant community known for its family-friendly atmosphere and extensive outdoor activities. This city offers a unique blend of golf courses and shopping areas, making it an ideal destination for both leisure and recreation. Visitors can enjoy various local attractions, including beautiful beaches and engaging theme parks, providing plenty of options for family outings. With its well-planned neighborhoods and active lifestyle, The Villages promises an enjoyable experience for all ages.
  • Winter Garden: Situated 24 miles from Leesburg, Winter Garden is a charming city that caters to families and entertainment seekers alike. The historic downtown area features delightful shops and a bustling shopping mall, perfect for a leisurely day out. Outdoor enthusiasts can explore nearby theme parks and even a film studio, offering a glimpse into the magic of movie-making. The combination of its quaint atmosphere and modern amenities makes Winter Garden a delightful stop on your vacation.
  • Ocala: About 30 miles from Leesburg, Ocala is the gateway to outdoor adventures and family fun. Known for its beautiful parks and recreational areas, this city offers numerous activities for nature lovers, including hiking, golfing, and exploring the scenic countryside. With a range of attractions like sports facilities and convention centers, Ocala is also a hub for events and gatherings. Its welcoming environment and diverse offerings make it a must-visit destination for travelers seeking an adventurous experience.

Best time to go to Leesburg

If you're planning a trip to Leesburg, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs in February to March and July, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January58.5°F (14.7°C)Light RainMostly SunnyAverageSlightly High
February62.6°F (17.0°C)Light RainMostly SunnyAverageAverage
March66.2°F (19.0°C)Light RainMostly SunnySlightly HighSlightly High
April71.8°F (22.1°C)Light RainMostly SunnySlightly HighAverage
May76.6°F (24.8°C)Light RainMostly SunnySlightly HighSlightly Low
June80.2°F (26.8°C)Light RainMostly SunnyAverageAverage
July81.5°F (27.5°C)Moderate RainMostly SunnyAverageAverage
August81.5°F (27.5°C)Moderate RainMostly SunnySlightly LowSlightly Low
September79.0°F (26.1°C)Light RainMostly SunnySlightly LowSlightly Low
October73.6°F (23.1°C)Light RainMostly SunnySlightly LowAverage
November66.4°F (19.1°C)Light RainMostly SunnyAverageAverage
December62.4°F (16.9°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save money on your upcoming travels? Being flexible with your travel dates can make a big difference, as prices can fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect fit for your needs!

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner truly pays off! When you join our travel rewards program, One Key, you'll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash™ on qualifying reservations. Sign up today and begin your journey to savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new trips, keep your travel arrangements on track, or organize your existing bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Lively Leesburg will entice you

The area's live music and festivals are just a few of the reasons to vacation in Leesburg. Renowned for its horseback riding, lake and golfing, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Leesburg

Are you hoping to find things to do during your stay? Travelers enjoy fun activities like golfing and biking. Venture out of your vacation home and experience everything that makes Leesburg a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Continental Country Club (6.7 mi / 10.7 km)
  • Mission Inn Golf Resort - El Campeon (8.3 mi / 13.3 km)
  • Harbor Hills Country Club (8.3 mi / 13.3 km)
  • TableTop Team Trivia (9.2 mi / 14.8 km)
  • Nancy Lopez Legacy Golf & Country Club (13.9 mi / 22.4 km)
  • Lakeridge Winery (14.2 mi / 22.9 km)

Exploring the natural features in Leesburg

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Leesburg is a great place to get outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Venetian Gardens (0.4 mi / 0.7 km)
  • Lake Griffin State Park (3.3 mi / 5.3 km)
  • Treasure Island (4.3 mi / 6.9 km)
  • Lake Okahumpka Park (7.7 mi / 12.5 km)
  • Lake Dora (10.9 mi / 17.6 km)
  • Donnelly Park (14.2 mi / 22.8 km)

Transportation to and around Leesburg

The nearest airport is in Leesburg, FL (LEE-Leesburg Intl.), located 4.4 mi (7.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Orlando Sanford Intl. Airport (SFB), which is 38.5 mi (62 km) away.

Frequently asked questions

What is the best area to stay in Leesburg when booking a vacation rental?
Haines Creek is one of the more desired locations for a vacation home in Leesburg. Stay here and enjoy all the convenience and privacy that comes with having a place to yourself.
How much does it cost to rent a vacation rental in Leesburg?
The average price for a vacation rental in Leesburg is based on several factors, like season, length of stay and property type. Whether you’re dreaming about a villa with space for extended family or a cozy cabin ideal for just you and the kids, just enter your dates of travel to find stays with great value.
How much does it cost to rent a beach house in Leesburg?
The average price for a vacation home near the beach in Leesburg will depend on when you’ll be there and the type and size of property you want. Find prices easily and quickly on Vrbo by entering your preferred travel dates and destination. Then use the filters to select the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.
What are the top attractions for families in Leesburg?
There’s no time for boredom during your Leesburg trip with these family-friendly attractions to explore:

  • ViaPort Florida
  • Plantation Golf Club

How old do you have to be to rent a vacation rental in Leesburg?
The minimum required age is normally 16, 18 or 21. It can vary from property to property on Vrbo, so check the rules of your chosen Leesburg vacation home before you book.
How long can I rent a vacation rental in Leesburg for?
The amount of time you can stay in a Leesburg vacation home for varies depending on the property. Just put in your travel dates to find options offering extended stays. They include all the things you need to make your extended trip more comfortable and enjoyable, like laundries and air conditioning. Some vacation rentals may also offer weekly or monthly discounted prices, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Leesburg?
In Leesburg, you’ll find some great discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it’s a weekend escape or a longer stay, we have a host of options to match your style.

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