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Leesburg vacation rentals

We found 1,696 vacation rentals — enter your dates for availability

Discover a selection of 37 homes, 10 apartments, 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 24 - Jul 31

Image gallery for 🧡Gorgeous Waterfront Oasis In Heart of The Villages 2 BR, 2 BA

Large living room
9.8 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)

🧡Gorgeous Waterfront Oasis In Heart of The Villages 2 BR, 2 BA

Lady Lake

7% off
Price is $142
$997 for 7 nights
All fees included
🧡Gorgeous Waterfront Oasis In Heart of The Villages 2 BR, 2 BA

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Find out more about Leesburg

Why visit Leesburg

  • Scenic Lakefront: Enjoy the picturesque waterfront, perfect for outdoor activities and relaxation.
  • Charming Neighborhoods: Explore friendly, romantic areas ideal for leisurely strolls and local experiences.
  • Family-Friendly Adventures: Discover a variety of parks and activities suited for all ages.
  • Diverse Accommodations: Choose from cozy cottages to spacious villas, catering to every traveler's needs.
  • Outdoor Enthusiast's Paradise: Embrace the natural beauty with numerous outdoor adventures and scenic spots.

Popular types of accommodation in Leesburg

If you're planning a getaway to Leesburg, you're in for a treat. Our vacation rental options include charming houses, spacious villas, and cozy cottages, all designed to meet your needs. Whether you're seeking a vacation home in Leesburg for a family retreat or a romantic escape, our selection of vacation homes in Leesburg offers something for everyone. Experience comfort and convenience while exploring this beautiful destination.

  • Houses: These are the top choice for visitors in Leesburg, offering spacious and comfortable stays ideal for families or groups.
  • Villas: A luxurious option, villas provide elegant spaces with amenities that cater to a relaxing getaway.
  • Cottages: Quaint and cozy, cottages offer a charming atmosphere perfect for a peaceful retreat.
  • Apartments: Convenient and practical, apartments are great for those seeking a home-like environment during their stay.
  • Cabins: Rustic and inviting, cabins are perfect for nature lovers looking for a unique experience.**

Top attractions in and around Leesburg

Leesburg, Florida, is a fantastic destination for outdoor enthusiasts and families seeking scenic experiences. With attractions like beautiful parks and nearby islands, visitors can enjoy a variety of activities tailored for all ages. Explore local points of interest and indulge in family-friendly adventures while soaking up the natural beauty of the area. There’s something for everyone in this charming city, making it a perfect spot for a memorable vacation.

  • Venetian Gardens: This beautiful park offers a serene escape with its picturesque landscapes, walking trails, and family-friendly amenities. Enjoy eco-friendly outdoor activities like picnicking, fishing, and boating in a tranquil setting surrounded by lush greenery.
  • UF Health Leesburg Hospital: A community-focused medical center offering comprehensive healthcare services. Its welcoming atmosphere is perfect for families seeking quality medical care, while also hosting various health and wellness programs.
  • The Villages Market Square: A vibrant modern square that features shopping, dining, and entertainment options. Experience lively events, live music, and a bustling atmosphere, making it a great spot for socializing and enjoying city life.

Things to do recommended for couples

For a romantic getaway in Leesburg, explore the luxurious vibes at Continental Country Club, only 7 miles away, or unwind at Water Oak Country Club Estates, 8 miles out. Don't miss the serene atmosphere at Glenview Champions Country Club, located 12 miles from the heart of Leesburg.

Things to do recommended for families

Families visiting Leesburg can have a fantastic time at the Leesburg Splash Park, where kids can enjoy water slides and play areas. Additionally, they can explore the scenic Lake Harris, perfect for picnicking and fishing, providing a fun outdoor experience for everyone.

Things to do recommended for groups

Explore the scenic Lake Harris by renting pontoon boats for a fun day on the water, or visit the Leesburg Historical Museum to dive into the local history. Don’t miss the vibrant local markets for unique shopping and delicious food options.

*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 Leesburg

If you're planning a trip with a group, family, pets, or are interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Leesburg with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Leesburg with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding 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 isn't truly fulfilling without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Leesburg: If you're seeking 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Leesburg

Leesburg, Florida, offers an unforgettable vacation experience with its picturesque waterfront and vibrant city atmosphere. Explore the scenic Lakefront City, perfect for outdoor adventures and family-friendly activities. Discover charming neighborhoods that are rich in friendly vibes and romantic spots, ideal for excursions. Whether you’re strolling through Leesburg Center or enjoying lakeside views, this destination promises a delightful blend of relaxation and exploration for every traveler.

  • Fruitland Park: Located a mere 4 miles from Leesburg, Fruitland Park is a charming city that invites visitors to experience its beautiful outdoor scenery and family-friendly atmosphere. Travelers can enjoy recreational areas perfect for picnics and outdoor activities, along with local shopping centers. For those seeking adventure, nearby attractions include serene lakes, the stunning national state park, and thrilling theme parks that promise fun for all ages. The blend of nature and recreation makes Fruitland Park an ideal spot for a relaxing getaway.
  • Silver Lake: Nestled within the Leesburg area, Silver Lake is a quaint village that offers a picturesque setting for visitors looking to enjoy outdoor activities and romantic scenery. The village features recreational areas where you can unwind and enjoy nature, along with several shopping areas and a mall center for leisurely strolls. The nearby lake and beach provide perfect spots for relaxation, while the vibrant town neighborhood creates a welcoming atmosphere. Whether you're looking for a peaceful day by the water or shopping, Silver Lake has something for everyone.
  • Lisbon: This charming village, also located in the Leesburg area, is a hidden gem perfect for travelers seeking a romantic and scenic escape. Lisbon offers lovely recreational areas where visitors can bask in the beauty of nature. With its proximity to a serene lake, inviting town neighborhood, and a delightful botanical garden, it’s an excellent destination for those who appreciate outdoor beauty and tranquility. Lisbon's serene ambiance makes it a perfect spot for a leisurely day trip or a romantic outing.

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 from January to March, while off-peak times, like May and August to September tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January58.5°F (14.7°C)Light RainMostly SunnyModerately HighAverage
February62.6°F (17.0°C)Light RainMostly SunnyModerately HighSlightly High
March66.2°F (19.0°C)Light RainMostly SunnyModerately HighSlightly High
April71.8°F (22.1°C)Light RainMostly SunnyAverageAverage
May76.6°F (24.8°C)Light RainMostly SunnyModerately LowAverage
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 SunnyModerately LowSlightly Low
September79.0°F (26.1°C)Light RainMostly SunnyModerately LowSlightly Low
October73.6°F (23.1°C)Light RainMostly SunnyAverageSlightly Low
November66.4°F (19.1°C)Light RainMostly SunnyAverageAverage
December62.4°F (16.9°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you interested in saving money on your next getaway? One effective strategy is to remain flexible with your travel dates, as prices can vary. Additionally, booking 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.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new trips, manage ongoing arrangements, and review your bookings. Your saved or reserved properties are organized into categories: Potential, Upcoming, or Current Trips. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • Mission Inn Golf Resort - El Campeon (8.3 mi / 13.3 km)
  • Harbor Hills Country Club (8.3 mi / 13.3 km)
  • Cane Garden Country Club (8.9 mi / 14.4 km)
  • Glenview Champions Country Club (12.4 mi / 19.9 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)
  • 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)
  • Lake Weir (14.8 mi / 23.9 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, Florida, United States of America when booking a vacation rental?
When looking for the best area to stay in Leesburg, Florida, consider the charming downtown district, known for its historic character and vibrant setting. This area is not only picturesque but also close to a variety of attractions, including the scenic Venetian Gardens, where you can enjoy beautiful landscapes and recreational activities. Additionally, downtown Leesburg features a selection of local shops, cafes, and restaurants that provide a taste of the community's flavor.

Another great option is the area surrounding Lake Harris, which offers a tranquil setting with stunning views and opportunities for water activities. This region is ideal for those who appreciate nature and want to unwind by the lake. The proximity to attractions like the nearby Lake County Historical Museum makes it an excellent choice for visitors interested in the local history and culture.
How much does it cost to rent a vacation home in Leesburg?
Prices for vacation rentals in Leesburg 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 Leesburg 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 Leesburg vacation house rentals?
You can find great discounts on house rentals in Leesburg 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 Leesburg?
In Leesburg, vacation houses are the most popular type of rental, with around 27 available throughout the area. These homes typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many houses also feature outdoor spaces such as patios or gardens, superb for enjoying the pleasant Florida weather. Additionally, there are several apartments, cottages, and mobile homes, which provide diverse options for travelers looking for unique accommodations.
Are there any family house rentals in Leesburg?
In Leesburg, Florida, there are some family-friendly house rentals available, with around 20 options to choose from. This charming city offers a variety of spacious homes that cater to families, featuring amenities such as full kitchens for preparing meals, comfortable living areas, and outdoor spaces superb for kids to play. Many properties also come equipped with conveniences like air conditioning and Wi-Fi to enhance the stay.

Visitors will appreciate the proximity to local attractions, including the scenic Lake Harris and the vibrant downtown area, where they can explore shops, restaurants, and parks. Leesburg also hosts various events throughout the year, providing families with opportunities for entertainment and community engagement.
Can I rent a vacation home with a pool or hot tub in Leesburg?
In Leesburg, Florida, there are several vacation homes available for rent that feature pools or hot tubs, with around 10 options to choose from. This charming city, located near the stunning Harris Chain of Lakes, offers a variety of neighborhoods where these rentals can be found. Many properties come equipped with private swimming pools, hot tubs, outdoor patios, and fully equipped kitchens, making them ideal for families and groups looking to relax and enjoy the Florida sunshine. Some homes may also include amenities such as game rooms or spacious backyards, great for outdoor gatherings and leisure activities.
Can I find long-stay vacation rentals in Leesburg?
A long-stay vacation rental in Leesburg 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 Leesburg?
In Leesburg, travelers will find a variety of pet-friendly house rentals that cater to those looking to enjoy a getaway with their furry companions. With 16 options available, visitors can expect a range of amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, ideal for families or groups. Many properties also feature outdoor spaces like patios or decks, great for relaxing in the Florida sunshine.

The area is known for its friendly atmosphere and is close to several parks and recreational spaces where pets are welcome. The nearby Venetian Gardens offers scenic walking trails and open spaces, making it a great spot for leisurely strolls with pets. Additionally, the Lake Harris area provides opportunities for fishing and boating, with many vacation rentals conveniently located near the water.
Are there any remote work vacation rentals in Leesburg?
In Leesburg, Florida, there are numerous options for remote work vacation rentals, with around 39 properties available. These rentals cater to travelers seeking a comfortable environment to work while enjoying their stay. Most accommodations come equipped with essential amenities such as high-speed Wi-Fi, providing reliable internet access for video calls and online tasks. Many properties also offer free Wi-Fi in both the rooms and common areas, ensuring connectivity throughout the stay.

Travelers can expect a range of options, including spacious homes with dedicated workspaces, comfortable living areas, and well-equipped kitchens for convenient meal preparation. The scenic surroundings of Leesburg, with its charming downtown and beautiful lakes, create a pleasant backdrop for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Leesburg vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Leesburg 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 Leesburg?
In Leesburg, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals at their convenience. Many properties offer onsite parking, making it easy for guests to come and go without the hassle of street parking. Outdoor spaces such as decks or patios are common, providing a lovely area to relax and enjoy the Florida sunshine. Additionally, rentals often include coffee and tea makers for a comforting start to the day, along with blenders for those wanting to whip up smoothies or other beverages.
When is the best time to visit Leesburg for a vacation rental?
The best time to visit Leesburg for a vacation rental is during September, when the summer crowds begin to thin out, yet the weather remains delightful for outdoor activities. The peak season runs from July to September, attracting visitors eager to explore the natural beauty and recreational opportunities that Leesburg offers, especially around the picturesque Harris Chain of Lakes.

Throughout September, you can expect comfortably warm temperatures ranging from the mid-60s to the low 90s Fahrenheit, ideal for enjoying activities such as boating, fishing, and hiking. The pleasant climate also makes it an excellent time for sightseeing, as you can explore local attractions like the historic downtown area and the scenic parks without the hustle and bustle of the peak summer months.

If you're looking for a more budget-friendly option, November presents a wonderful opportunity to experience the tranquility of Leesburg, with fewer tourists and a chance to enjoy the area's natural beauty at a more relaxed pace. The fall weather is still inviting, allowing for scenic strolls and outdoor exploration.
How early should I book a Leesburg vacation rental?
Book your Leesburg 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 Leesburg, Florida, United States of America?
In Leesburg, Florida, visitors can enjoy a variety of attractions that showcase the area's charm and natural beauty. The historic downtown area features quaint shops, local eateries, and beautiful architecture, making it a lovely spot for a leisurely stroll. The Leesburg Heritage Museum offers insights into the local history and culture, while the nearby Venetian Gardens provides scenic walking paths, picnic spots, and a picturesque view of Lake Harris.

For outdoor enthusiasts, Lake Griffin State Park is a fantastic destination, offering opportunities for hiking, fishing, and wildlife viewing. The park's trails wind through lush landscapes and along the shores of the lake, providing a serene escape from urban life.
Can I change or cancel my Leesburg home rental booking on Vrbo?
To find Leesburg 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 Leesburg 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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