Photo by David Cate

Leesburg holiday lettings

We found 1,687 holiday rentals — enter your dates for availability

Discover a selection of 34 homes, 11 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:29 May - 5 Jun

Image gallery for Perfect for FAMILY REUNIONS. Close by The Villages & shopping yet very private.

Pool, patio table w/ 6 chairs, hot tub, lounge chairs, BBQ
10 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)

Perfect for FAMILY REUNIONS. Close by The Villages & shopping yet very private.

Lady Lake

9% off
Price is £3,186
for 7 nights, 1 home
£455 per night
includes taxes & fees
Perfect for FAMILY REUNIONS. Close by The Villages & shopping yet very private.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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 Griffin (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)

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, the downtown area stands out as an excellent choice. This vibrant neighbourhood offers a charming mix of historic architecture and modern conveniences, making it an appealing place for visitors. Here, you can enjoy a leisurely stroll along the picturesque streets, lined with quaint shops and delightful cafés.

One of the highlights of staying in this area is the proximity to the beautiful Venetian Gardens, a lovely park featuring scenic walking paths, stunning flower displays, and a serene lake superb for picnicking or simply relaxing. Additionally, the historic Leesburg Museum provides an interesting glimpse into the local heritage and culture.

There are numerous properties available in downtown Leesburg, suiting various tastes and budgets, which makes it easy to find a suitable holiday rental.
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 holiday rental, with approximately 54 available throughout the area. These spacious properties often feature multiple bedrooms, fully equipped kitchens, and outdoor patios or decks, making them ideal for families or groups seeking comfort and convenience. Additionally, there are around 16 apartments, which provide a more compact option, typically including kitchen facilities, living areas, and communal amenities. Several cottages and mobile homes are also scattered around, offering unique stays that cater to those looking for a more rustic experience. Campsites are available as well for outdoor enthusiasts wanting to enjoy the natural surroundings.
Are there any family house rentals in Leesburg?
In Leesburg, Florida, there are numerous family-friendly house rentals available—around 20 options throughout the area. This charming locale offers a variety of spacious homes superb for families, many featuring ample living spaces, fully equipped kitchens for preparing meals together, and outdoor areas where children can play safely. Common amenities include Wi-Fi and air conditioning, ensuring a comfortable stay for all.

Families will appreciate the proximity to several parks and recreational spots, such as the picturesque Venetian Gardens, which boasts walking trails, picnic areas, and a playground. Additionally, the nearby Lake Harris offers opportunities for fishing and boating, making it an ideal spot for outdoor adventures.
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 or hot tubs, with around 10 options to choose from. This charming town, situated near the beautiful Harris Chain of Lakes, offers a variety of properties in residential neighbourhoods that cater to families and groups seeking relaxation and fun.

Travellers can expect a range of amenities in these rentals, typically including private pools and hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens ideal for preparing meals. Some properties may also feature game rooms, barbecue grills, and lush gardens, providing an inclusive setting for entertaining or unwinding after a day of exploring the local attractions.
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, providing a range of options for travellers with pets. Many of these properties come equipped with amenities such as spacious backyards, allowing pets to roam freely, as well as fully equipped kitchens and comfortable living areas for relaxation.

The area is also conveniently located near parks where pets can enjoy some outdoor time. For instance, the nearby Venetian Gardens Park features walking trails and picnic areas, making it a lovely spot for owners and their pets to enjoy the outdoors. Additionally, the local community often has pet-friendly cafes and shops, ideal for those travelling with furry companions.
Are there any remote work holiday rentals in Leesburg?
In Leesburg, Florida, there are numerous options for remote work holiday rentals, with around 78 available. This charming town offers a variety of properties that cater to those looking to combine work and leisure. Many rentals provide essential amenities such as free Wi-Fi, which is often available both in the rooms and in public areas. This ensures that guests can stay connected and productive during their stay.

The town is well-situated near picturesque lakes and parks, offering opportunities for outdoor activities during breaks from work. Additionally, you'll find local cafes and restaurants that provide comfortable environments for remote working. 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 holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature onsite parking, making it convenient for those travelling with vehicles. Additionally, rentals often come with decks or patios, providing outdoor spaces to relax and enjoy the pleasant Florida weather. Guests can also expect amenities like coffee and tea makers for a quick morning brew, as well as blenders for preparing smoothies or other refreshments.
When is the best time to visit Leesburg for a holiday rental?
September is the most popular time to visit Leesburg, Florida, as the summer heat begins to diminish and outdoor activities flourish. This period falls within the peak season, which spans from July to September, attracting families and adventure seekers looking to indulge in local festivals, fishing, and boating on the beautiful lakes surrounding the area.

With temperatures ranging from a comfortable 20 to 30 degrees Celsius, September offers ideal weather for exploring the scenic landscapes and historic downtown Leesburg. Visitors can enjoy leisurely strolls along the waterfront, partake in community events, or even venture out to the nearby parks for hiking and picnicking amidst nature.

For those looking for a more budget-friendly option, consider visiting in November. This month often features pleasant weather, with fewer crowds, allowing for a more relaxed atmosphere to explore the local attractions and enjoy the vibrant fall foliage.
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 showcase the area's natural beauty and local culture. The picturesque Lake Harris is a popular spot for fishing, boating, and picnicking, offering scenic views and outdoor activities. Nearby, the historic downtown area features charming shops and cafes, superb for leisurely strolls.

The Leesburg Heritage Museum provides insights into the local history and culture, making it an informative stop for those interested in the area's past. For nature enthusiasts, the nearby Lakeridge Winery and Vineyards offers wine tastings and beautiful views of the surrounding countryside, while the Florida Waterman's Park features walking trails and serene picnic areas by the water.
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.

More holiday ideas