Leesburg holiday homes

We found 1,670 holiday rentals — enter your dates for availability
Discover a selection of 37 homes 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:18 Dec - 25 Dec

Living area
Living area
Private kitchen
Exterior
Exceptional
(114 reviews)

Perfect Location Between Brownwood & Lake Sumter

The Villages

11% off
NZ$2,079
for 7 nights, 1 villa
NZ$297 per night
includes taxes & fees
Perfect Location Between Brownwood & Lake Sumter
Pool
Interior
Interior
Property grounds
Exceptional
(30 reviews)

Boat Friendly & Private Pool Near The Villages

Leesburg

5% off
NZ$11,907
for 7 nights, 1 home
NZ$1,701 per night
includes taxes & fees
Boat Friendly & Private Pool Near The Villages
Outdoor dining
Pool
Interior
Living area
Exceptional
(17 reviews)

Private Pool Oasis + Hot Tub ,Quiet Luxury in The Villages, Pet Friendly

The Villages

12% off
NZ$4,662
for 7 nights, 1 home
NZ$666 per night
includes taxes & fees
Private Pool Oasis + Hot Tub ,Quiet Luxury in The Villages, Pet Friendly
Living area
A thousand square feet of dock area including 16x20 covered pavilion with BBQ.
Summer Kitchen
Property grounds
Exceptional
(102 reviews)

Sunrise to Sunset on private 900 sq ft dock with BBQ!

Tavares

16% off
NZ$1,731
for 7 nights, 1 room
NZ$247 per night
includes taxes & fees
Sunrise to Sunset on private 900 sq ft dock with BBQ!
Terrace/patio
Private kitchen
Living area
Interior
Exceptional
(11 reviews)

Modern Brick Rural Home

Clermont

8% off
NZ$4,266
for 7 nights, 1 home
NZ$609 per night
includes taxes & fees
Modern Brick Rural Home
Room
Interior
Dining
Property grounds
Exceptional
(19 reviews)

Mount Dora Home near the historic center

Mount Dora

11% off
NZ$1,908
for 7 nights, 1 home
NZ$273 per night
includes taxes & fees
Mount Dora Home near the historic center
Living area
Private kitchen
Interior
Room
Wonderful
(5 reviews)

Charming 2-bedroom house in serene Lady Lake Villages home with AC

Lady Lake

8% off
NZ$2,083
for 7 nights, 1 home
NZ$298 per night
includes taxes & fees
Charming 2-bedroom house in serene Lady Lake Villages home with AC
Interior
Room
Dining
Terrace/patio
Very good
(11 reviews)

Lakefront Views-Private Porch and Deck- Close to the Villages in Leesburg

Fruitland Park

11% off
NZ$1,468
for 7 nights, 1 home
NZ$210 per night
includes taxes & fees
Lakefront Views-Private Porch and Deck- Close to the Villages in Leesburg
Interior
Private kitchen
Living area
Dining
Exceptional
(33 reviews)

Lakefront Home on Lake Griffin / Harris chain of lakes and close to the Villages

Fruitland Park

8% off
NZ$4,086
for 7 nights, 1 home
NZ$584 per night
includes taxes & fees
Lakefront Home on Lake Griffin / Harris chain of lakes and close to the Villages
Private kitchen
Interior
Living area
Room
Exceptional
(8 reviews)

Barndominium at Dirty Dog Organic Farm

Leesburg

7% off
NZ$1,896
for 7 nights, 1 home
NZ$271 per night
includes taxes & fees
Barndominium at Dirty Dog Organic Farm
Outside of Home
Outdoor dining
Living Room looking out to the Tremain Street. A one-way road with bicycle lane.
Private kitchen
Exceptional
(40 reviews)

Closest Stay to Downtown Mt Dora - Renovated - Walk Everywhere

Mount Dora

12% off
NZ$5,250
for 7 nights, 1 home
NZ$750 per night
includes taxes & fees
Closest Stay to Downtown Mt Dora - Renovated - Walk Everywhere
Private kitchen
Exterior
Private kitchen
Interior
Exceptional
(13 reviews)

Spacious lake view home near Historic Downtown Mount Dora!

Eustis

7% off
NZ$3,102
for 7 nights, 1 home
NZ$443 per night
includes taxes & fees
Spacious lake view home near Historic Downtown Mount Dora!
Golf
Property grounds
Private kitchen
Interior
Exceptional
(84 reviews)

Walk to Spanish Springs, free 4 seater golf cart, covered patio! Pools nearby!!

Lady Lake

7% off
NZ$1,940
for 7 nights, 1 home
NZ$277 per night
includes taxes & fees
Walk to Spanish Springs, free 4 seater golf cart, covered patio! Pools nearby!!
Welcome to The Den Downtown!
Terrace/patio
Room
Private kitchen
Exceptional
(34 reviews)

Walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath

Mount Dora

7% off
NZ$2,843
for 7 nights, 1 cottage
NZ$406 per night
includes taxes & fees
Walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath
Dining
Terrace/patio
Room
Exterior
Wonderful
(10 reviews)

Cozy Cottage Under the Oaks, Pet-Friendly and Minutes from Mt. Dora

Mount Dora

7% off
NZ$2,135
for 7 nights, 1 home
NZ$305 per night
includes taxes & fees
Cozy Cottage Under the Oaks, Pet-Friendly and Minutes from Mt. Dora
Outdoor dining
Living area
Exterior
Property grounds
Exceptional
(20 reviews)

Gorgeous 3 bd-2 bth in Fenney w/4-seat Cart; Near Brownwood, Sawgrass, Eastport

Wildwood

7% off
NZ$2,968
for 7 nights, 1 home
NZ$424 per night
includes taxes & fees
Gorgeous 3 bd-2 bth in Fenney w/4-seat Cart; Near Brownwood, Sawgrass, Eastport
Private kitchen
Outdoor dining
Dining
Room
Exceptional
(17 reviews)

Sunny Getaway: Easy Access to Orlando & the Shore!

Leesburg

8% off
NZ$2,270
for 7 nights, 1 home
NZ$324 per night
includes taxes & fees
Sunny Getaway: Easy Access to Orlando & the Shore!
Private kitchen
Living area
Terrace/patio
Exterior detail
Exceptional
(68 reviews)

1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!

Mount Dora

8% off
NZ$4,921
for 7 nights, 1 home
NZ$703 per night
includes taxes & fees
1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!
Comfortable space in living room with 55 inch TV
Interior
Interior
Screen back porch with seating
Exceptional
(10 reviews)

Charming bungalow perfect for base camp for anglers and sports enthusiasts.

Tavares

8% off
NZ$2,273
for 7 nights, 1 home
NZ$325 per night
includes taxes & fees
Charming bungalow perfect for base camp for anglers and sports enthusiasts.
View of backyard and Lake Franklin canal from the back porch
Sitting area on back porch
Kitchen with view of bedrooms and bathrooms down the hallway.
Property grounds
Exceptional
(121 reviews)

Quiet and peaceful yet walk to Charming Downtown MT. Dora

Mount Dora

12% off
NZ$2,229
for 7 nights, 1 home
NZ$318 per night
includes taxes & fees
Quiet and peaceful yet walk to Charming Downtown MT. Dora
Interior
Interior
Dining
Interior
Exceptional
(15 reviews)

3 min drive to DT Mount Dora!

Mount Dora

8% off
NZ$5,030
for 7 nights, 1 home
NZ$719 per night
includes taxes & fees
3 min drive to DT Mount Dora!

  • 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, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • 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)
  • Cane Garden Country Club (8.9 mi / 14.4 km)
  • Orange Blossom Hills Golf & Country Club (10.6 mi / 17 km)
  • Glenview Champions Country Club (12.4 mi / 19.9 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 Sumter (9 mi / 14.6 km)
  • Lake Dora (10.9 mi / 17.6 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.
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.
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 Bookabach.
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.
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.
Are all fees included in the Leesburg holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Leesburg holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Leesburg holiday homes?
You can find great discounts on holiday homes in Leesburg on Bookabach, 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.
Can I change or cancel my Leesburg holiday home booking on Bookabach?
To find Leesburg holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Leesburg?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Leesburg holiday home?
Book your Leesburg holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Leesburg?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Leesburg to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas