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Leesburg holiday lettings

We found 1,644 holiday rentals — enter your dates for availability

Discover a selection of 34 homes, 12 apartments and other holiday rentals in Leesburg that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a garden and pool. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Leesburg

Showing deals for:20 Mar - 27 Mar

Image gallery for Pet Friendly, Modern Tiny Home in Vibrant Clermont!

Private kitchen
10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Pet Friendly, Modern Tiny Home in Vibrant Clermont!

Clermont

8% off
Price is £1,203
for 7 nights, 1 villa
£172 per night
includes taxes & fees
Pet Friendly, Modern Tiny Home in Vibrant Clermont!

Find spaces that suit your style

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Why visit Leesburg

  • Idyllic outdoor activities: Enjoy a range of outdoor pursuits in Leesburg, perfect for families and nature lovers.
  • Charming town atmosphere: Stroll through the Heart of Leesburg, filled with local eateries and a friendly vibe.
  • Scenic lakeside views: Relax by Lake Harris, where you can enjoy tranquil moments and evening gatherings.
  • Proximity to beautiful beaches: Take a short trip to nearby Folly Beach for a delightful day by the sea.
  • Varied accommodation options: Choose from cosy cottages to spacious villas for a comfortable stay.

Popular types of accommodation in Leesburg

Discover the charm of Leesburg with a selection of delightful vacation rentals. Whether you prefer a private vacation home, a cosy cottage, or a spacious villa, there’s something to suit every traveler's needs. Our friendly rentals in Leesburg offer transparency and reassurance, ensuring a memorable stay. Explore house rentals in Leesburg and find your perfect getaway today!

  • Houses: The top choice for holiday rentals in Leesburg, offering spacious and comfortable living for families or groups.
  • Villas: A popular option for those seeking luxurious surroundings and amenities during their stay in Leesburg.
  • Cottages: Quaint and charming, these are ideal for a homely retreat in a picturesque setting.
  • Apartments: Convenient and versatile, perfect for couples or solo travellers looking for a self-catering experience.
  • Cabins: A rustic option that provides a unique experience amidst nature, popular among outdoor enthusiasts.**

Top attractions in and around Leesburg

Leesburg, Florida, is an idyllic destination for outdoor enthusiasts and families alike, offering a delightful blend of scenery and activities. Visitors can explore a variety of points of interest, including picturesque islands, serene parks, and vibrant modern squares. Whether you seek a beach escape or a charming city experience, Leesburg promises a memorable holiday filled with natural beauty and engaging attractions.

  • Venetian Gardens: A picturesque park nestled in Leesburg, Venetian Gardens boasts beautiful landscapes and eco-friendly features, perfect for family outings. Enjoy leisurely strolls along the water's edge and explore the vibrant flora.
  • Lake Griffin State Park: Located 1.9km from Leesburg, this national park offers thrilling outdoor adventures amidst stunning scenery. Engage in hiking, fishing, and birdwatching while soaking in the natural beauty of Florida.
  • The Villages Market Square: Situated 5.6km away, this modern square is a hub of activity, featuring shops, dining, and entertainment. Experience the lively atmosphere and vibrant city vibes, perfect for an evening out.

Things to do recommended for couples

For a romantic getaway in Leesburg, indulge in luxury at the Continental Country Club, savour a meal at the family-friendly Cane Garden Country Club, or enjoy an entertaining evening at The Orange Blossom Opry. These experiences promise to create lasting memories for you both.

Things to do recommended for families

Families visiting Leesburg, Florida, can enjoy the Lake Sumter Sports Complex for wellness activities and relaxation, or take a short trip to Marsh Memorial Park, just 7.5km away, offering a tranquil outdoor experience perfect for family bonding.

Things to do recommended for groups

In Leesburg, groups can enjoy a lively atmosphere at Spanish Springs Town Square for shopping, challenge themselves at the Plantation Golf Club, or explore the diverse offerings at ViaPort Florida, a vibrant shopping mall perfect for family entertainment.

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

When travelling with a group, family, pets, or planning for a longer stay, it's important to set the right priorities when filtering your options. Here are some helpful booking tips for Vrbo.

  • Traveling to Leesburg with a group: Think about how many bedrooms you require, along with additional features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily refine your search for all of these options, and more, on Vrbo.
  • Traveling to Leesburg with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, as well as ensuring access to suitable amenities, like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Leesburg: For many, a family holiday isn't truly fulfilled without their four-legged companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Leesburg: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. 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 a delightful blend of outdoor family fun and scenic beauty. Explore the charming Heart of Leesburg, perfect for leisurely strolls and local eateries. Enjoy the serene views at Lake Harris, and gather around a firepit for a cosy evening. For a relaxing beach day, venture to nearby Folly Beach. With its friendly atmosphere and romantic excursions, Leesburg is an ideal destination for your next holiday.

  • Lady Lake: Located 5.0km from Leesburg, Lady Lake is a charming city that caters to those seeking an outdoor and family-friendly experience. Here, you can enjoy a variety of activities such as golfing at well-maintained courses, shopping in local boutiques, and relaxing by the picturesque lakes. With its inviting parks and proximity to attractions like a beach and a theme park, Lady Lake is perfect for a day of adventure or a leisurely stroll amidst nature.
  • Fruitland Park: Just 2.5km from Leesburg, Fruitland Park is an idyllic city known for its stunning scenery and romantic atmosphere. The area is perfect for outdoor pursuits, offering recreational areas and beautiful golf courses. Visitors can explore nearby lakes and the national state park, providing ample opportunities for hiking and picnicking. With its charming landscape and tranquil settings, Fruitland Park is a delightful spot for couples and nature lovers alike.
  • Silver Lake: Situated within the vicinity of Leesburg, the village of Silver Lake offers a welcoming atmosphere for families and nature enthusiasts. With its recreational areas and resorts, it’s a fantastic place to unwind and enjoy the outdoors. The nearby lake and national state park provide ample opportunities for exploration, while a local theme park adds an element of excitement for families. Silver Lake is a lovely destination for those looking to combine relaxation with outdoor fun.

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 August to October 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 HighAverage
March66.2°F (19.0°C)Light RainMostly SunnyModerately HighSlightly High
April71.8°F (22.1°C)Light RainMostly SunnyAverageSlightly High
May76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
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 SunnyModerately LowSlightly 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

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new adventures, pick up right where you left off, or review and arrange your travel plans. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Lively Leesburg will entice you

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

Activities and attractions in Leesburg

Are you hoping to find attractions to see while you're in the area? Travellers enjoy fun activities like golfing and cycling. Venture out of your cosy holiday rental and experience everything that makes Leesburg a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • 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 take in the scenery, Leesburg is a great place to spend some time outside. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Venetian Gardens (0.4 mi / 0.7 km)
  • Lake Griffin State Park (3.3 mi / 5.3 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)
  • Little Lake Weir (15.6 mi / 25.2 km)

Transport to and around Leesburg

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

Frequently asked questions

What is the best area to stay in Leesburg when booking a holiday rental?
When considering a holiday rental in Leesburg, Florida, a popular area to stay in is the historic downtown district. This charming neighbourhood offers a delightful atmosphere with its picturesque streets and a range of local shops, cafes, and restaurants, making it a vibrant spot for visitors. The downtown area is also close to several attractions, including the beautiful Venetian Gardens, which features stunning botanical displays and serene walking paths by the water.

Another appealing area is the Lake Harris region, known for its stunning lake views and recreational opportunities. This area is particularly great for those who enjoy outdoor activities, as it provides easy access to boating, fishing, and hiking. Plus, it's just a short drive to the popular Lake Louisa State Park, where you can explore nature trails and enjoy picnicking amidst the beautiful scenery.
How much does it cost to rent a holiday home in Leesburg?
Prices for holiday 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 holiday 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 holiday rental accomodation in Leesburg?
In Leesburg, holiday houses are the most popular type of rental, with around 27 available throughout the area. These houses typically offer spacious living areas, fully equipped kitchens, and often include outdoor spaces such as patios or gardens, great for enjoying the warm Florida weather. Additionally, there are several apartments, cottages, mobile homes, and cabins available, providing a variety of options for travellers. The holiday rentals in Leesburg cater well to families and groups, offering comfortable and homely accommodations close to local attractions such as Lake Harris and the scenic downtown area.
Are there any family house rentals in Leesburg?
In Leesburg, Florida, there are numerous family-friendly house rentals available, with around 21 options scattered throughout the area. This charming town boasts a variety of properties well-suited for families, offering spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play safely. Many of these homes also include amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.
Can I rent a holiday home with a pool or hot tub in Leesburg?
In Leesburg, Florida, there are several holiday homes available for rent that come with pools and hot tubs. This charming city, located near the beautiful Harris Chain of Lakes, offers a variety of neighbourhoods where travellers can find suitable rentals. Many properties feature private pools, spacious outdoor areas for relaxation, and hot tubs, providing ideal amenities for families or groups looking to unwind after a day of exploring.
Can I find long-stay holiday rentals in Leesburg?
A long-stay holiday rental in Leesburg 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 Leesburg?
In Leesburg, there are several pet-friendly house rentals available for travellers looking to enjoy a getaway with their furry companions. Many of these properties come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families and groups.
Are there any remote work holiday rentals in Leesburg?
In Leesburg, Florida, there are numerous remote work holiday rentals available, with around 34 options to choose from. Many of these properties are well-equipped to facilitate a productive work environment, featuring dedicated office spaces complete with desks, chairs, and computer monitors. Wi-Fi is typically high-speed, ensuring that you can stay connected while working from the comfort of your rental. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Leesburg holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Leesburg 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 Leesburg?
In Leesburg, popular rental amenities include complimentary Wi-Fi, well-equipped kitchens with microwaves, cookware, dishware, and utensils, as well as refrigerators. These amenities are commonly found in the area's holiday rentals, suiting travellers who appreciate the convenience of preparing their own meals while enjoying a comfortable stay.
When is the best time to visit Leesburg for a holiday rental?
September is the most popular time to visit Leesburg, Florida, as summer transitions into autumn. This month is particularly appealing for holidaymakers seeking a blend of pleasant weather and vibrant local events. The peak season runs from July through September, where visitors can enjoy the warm temperatures, typically in the high 20s to low 30s Celsius, superb for outdoor activities and sightseeing.

During this time, you can explore the picturesque Lake Harris, enjoy leisurely walks in the scenic parks, or delve into the local culture by attending various festivals that often take place in September. The comfortable climate allows for plenty of opportunities to relish the natural beauty of the area, making it an ideal choice for those looking to relax and unwind.

If you are considering a more budget-friendly option, November presents a wonderful opportunity to visit Leesburg. This month typically sees fewer tourists, giving you a chance to explore at a more leisurely pace. You can take advantage of the quieter surroundings to enjoy the local attractions without the hustle and bustle, all while still appreciating the area's charm.
How early should I book a Leesburg holiday rental?
Book your Leesburg holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Leesburg?
In Leesburg, Florida, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The picturesque Lake Harris provides opportunities for fishing, boating, and scenic picnics along its shores. Nearby, the Venetian Gardens offers lovely walking paths, gardens, and a playground, making it a great spot for families and nature lovers alike.
Can I change or cancel my Leesburg home rental booking on Vrbo?
To find Leesburg holiday 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 cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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