Best Holiday rentals and Airbnb offers in Leesburg, FL
Leesburg, FL
12/07 – 15/07
SG$243/nighttotal: SG$729 (3 )
Lakefront Retreat Patio + Grill Pet Friendly
2 4
apartment , Leesburg
This two-bedroom, two-bathroom flat in Leesburg offers a peaceful lakefront setting with direct patio access, located a short drive from attractions such as the Paul P. Williams Auditorium and Brownwood Paddock Square. Spanning 126 square meters, this pet-friendly apartment accommodates up to four guests and features a fully equipped kitchen, air conditioning, on-site laundry, and access to community amenities including a swimming pool and fitness centre.
9.6 21 reviews
Leesburg, FL
01/08 – 30/09
SG$163/nighttotal: SG$9780 (60 )
Great 3/2 Villages Home With Amenities Access
3 1
house , Leesburg
This brand-new three-bedroom patio villa is located in the Village of Lake Denham, The Villages, Florida, a short golf cart ride from Sawgrass Grove's shopping and entertainment, and a short drive from recreation centres and a golf course. The 130 square metre (1,400 square foot) property features an open-plan layout, sleeps six guests comfortably, includes a fully equipped kitchen with stainless-steel appliances and a wine chiller, and offers a 4-passenger golf cart for exploring local amenities.
10 22 reviews
Leesburg, FL
25/06 – 29/06
SG$310/nighttotal: SG$1240 (4 )
Paradise On Lake Harris Apt #202
1 2
apartment , Leesburg
This one-bedroom apartment is located in a peaceful neighbourhood in Leesburg, just 1 kilometre from Venetian Gardens and the boat ramp, 5 minutes from Lake Square Mall, and 20 minutes from The Villages Retirement Community. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience. The apartment offers 700 square feet of living space and can accommodate up to 4 guests. Guests can enjoy a private patio, a fire pit, a playground, a fully equipped kitchen, and a boat dock with direct access to Lake Harris.
10 25 reviews
Leesburg, FL
01/01 – 31/03
SG$255/nighttotal: SG$22695 (89 )
Lakefront Magic Wilderness Cabin
1 2
cabin , Leesburg
This Leesburg lakeside lodge, formerly situated in Walt Disney World's Fort Wilderness Campground, boasts a unique history and enjoys a tranquil one-acre setting amongst oak and cypress trees, close to Evans Park and approximately 10km from Mount Dora Lawn Bowling Club. Sleeping up to five guests in one bedroom and one bathroom, this self-catering property offers a fully equipped kitchen, air conditioning, internet access, a private dock, and a garden; wildlife viewing is a possibility due to its Certified Wildlife Habitat designation.
10 2 reviews
Leesburg, FL
12/07 – 19/07
SG$429/nighttotal: SG$3003 (7 )
Holiday Rv Park
3 8
apartment , Leesburg
This waterfront property is located near Leesburg, Florida, within 9.6 kilometres of Plantation Golf Club and Venetian Gardens, and within 14.4 kilometres of Lake Griffin and Lake Griffin State Park. This six-bedroom house, with a sofa bed, comfortably accommodates large families or groups of friends and features a private swimming pool, a fitness centre, a tennis court, a garden and a terrace, as well as a fully equipped kitchen.
9.8 6 reviews
Leesburg, FL
12/07 – 15/07
SG$301/nighttotal: SG$903 (3 )
Best Of The Villages! 2br/2ba Home & Amenity Access
2 4
apartment , Leesburg
This Okahumpka villa is situated within 14.5 kilometres of Plantation Golf Club, Venetian Gardens, and UF Health Leesburg Hospital, offering convenient access to local amenities and attractions. This two-bedroom, two-bathroom property boasts a 92 square metre floor area, a private patio, swimming pool, and gas grills, comfortably accommodating up to four guests and including free Wi-Fi.
9.5 16 reviews
Leesburg, FL
01/01 – 31/03
SG$268/nighttotal: SG$23852 (89 )
Charming Leesburg Cottage/ample Parking For Boats
3 2
apartment , Leesburg
This Leesburg flat offers convenient access to Venetian Gardens and Lake Harris, ideal for boating and fishing, and is just 8 minutes by car from the historic shops and eateries of downtown Leesburg, with Mt. Dora a short drive away. This property accommodates up to nine guests in three bedrooms and on a sofa bed, featuring a fully equipped kitchen, in-unit laundry, Smart TVs, and a spacious garden, with free parking for six vehicles available directly outside.
9.8 7 reviews
Leesburg, FL
01/08 – 30/09
SG$158/nighttotal: SG$9480 (60 )
Blissful Village Bungalow 2br-2ba & Membership Amentities
2 1
apartment , Leesburg
This brand-new, two-bedroom villa is located in the Village of Lake Denham, The Villages, Florida, a short golf cart ride (approximately 1.6km) from Sawgrass Grove shopping and dining and several recreation centres. The 109 square metre property boasts a spacious open-plan layout, sleeping four guests comfortably, and includes a fully equipped kitchen, smart TVs, a golf cart, and outdoor living space with a lanai and gas grill; highchair and Pack-n-Play available.
8.6 7 reviews
Leesburg, FL
01/01 – 31/03
SG$144/nighttotal: SG$12816 (89 )
Cottage 33, Pineapple Place - Dora Canal Court - A Downtown, Waterfront Community
1 2
house , Tavares
Cottage 33, a waterfront property in the Dora Canal Court community of Tavares, Florida, offers direct access to the Tavares canals and is situated 53 kilometres from Orlando Sanford International Airport. This recently renovated one-bedroom house boasts a 22-square-metre floor area, sleeps two guests, includes a fully equipped kitchenette, private patio with fireplace, barbecue facilities, and free Wi-Fi and parking.
9.2 25 reviews
Leesburg, FL
01/01 – 31/03
SG$295/nighttotal: SG$26255 (89 )
Lake Dora Escape: Canal Access & Seaplane Sights!
2 2
apartment , Tavares
This Tavares waterfront flat is located 0.8 km from a community boat ramp and 1.6 km from Main Street's shops and restaurants, offering direct access to Lake Dora. The 74 square metre property sleeps five, featuring two queen beds, two twin futons, a kitchen with fridge and microwave, a garden, parking, and shared amenities including a gas grill, fire pit, and screened porch; plus a Smart TV, board games, and poker table.
9.6 131 reviews
Leesburg, FL
12/07 – 15/07
SG$196/nighttotal: SG$588 (3 )
Welcome Small Dogs.. Elegant Villa, Golf Cart, Walk To Sumter Square, Sleep 6
2 4
house , The Villages
This two-bedroom villa in Virginia Trace is ideally located just a mile from The Villages Market Square and 2.4 miles from Cane Garden Country Club, offering easy access to shopping, dining, and entertainment. It has received excellent user ratings, making it a popular choice for travellers visiting The Villages. The villa comfortably accommodates up to eight guests and features a well-equipped kitchen, a private garden, and a swimming pool. Enjoy a relaxing stay with amenities like air conditioning, free Wi-Fi, a terrace, and ample parking.
9.8 14 reviews
Leesburg, FL
01/08 – 30/09
SG$185/nighttotal: SG$11100 (60 )
Tranquil Central Fl Retreat
3 1
apartment , Leesburg
This Leesburg holiday home is situated near Fern Prairie Preserve and within 5km of Lake Sumter Landing, offering easy access to Lake Square Mall, ViaPort Florida, and the Paul P. Williams Auditorium. The 121 square metre property boasts three bedrooms, two bathrooms, sleeps nine guests, and includes a sauna, spa, private garden, barbecue facilities, and free Wi-Fi.
Best family friendly Leesburg, FL holiday rentals
Among the 252 accommodations in Leesburg, FL, here are the 4 best family friendly rentals
10 15 reviews
Leesburg, FL
01/08 – 30/09
SG$170/nighttotal: SG$10200 (60 )
Venetian Gardens Home In Peaceful Neighborhood
3 1
apartment , Leesburg
This three-bedroom apartment is situated in Leesburg, Florida, just a 50-minute drive from both Disney World and the beaches, and is close to Venetian Gardens Park. It has received excellent user ratings. The apartment spans 165 square metres and can comfortably accommodate up to six guests. It offers a range of features, including a fully equipped kitchen, air conditioning, a garden, parking, and internet access. Guests can also enjoy access to a lakefront location, a quiet neighbourhood, and proximity to golf courses and nature reserves.
9.2 23 reviews
Leesburg, FL
05/07 – 31/08
SG$147/nighttotal: SG$8379 (57 )
Blissful Village Bungalow 2br-2ba & Membership Ame
1 1
apartment , Leesburg
This brand-new two-bedroom patio villa is located in the Village of Lake Denham within The Villages, Florida, a short golf cart ride from Sawgrass Grove's shopping and entertainment and several recreation centres. The 2-bedroom, 2-bathroom property offers an open-plan layout, sleeps four guests, and includes a fully equipped kitchen, 75" smart Roku TV, in-unit laundry, outdoor lanai with gas grill, highchair and Pack 'n' Play, plus a golf cart for easy access to local amenities.
9.6 21 reviews
Leesburg, FL
25/06 – 29/06
SG$294/nighttotal: SG$1176 (4 )
Centrally Located Family Friendly - One Gas Golf Cart, Seats 4 - Coastal Themed
3 2
apartment , The Villages
This three-bedroom apartment is ideally situated in Duval, The Villages, within easy reach of both Lake Sumter Landing Market Square and Brownwood Paddock Square, making it a perfect base for exploring all that The Villages has to offer. It has received excellent guest reviews, making it a popular choice for travellers. The spacious apartment, spanning 129 square metres, comfortably accommodates up to six guests. It comes equipped with a range of amenities including a swimming pool, a spa, a garden, and two golf carts for exploring the area, ensuring a relaxing and enjoyable stay.
9.6 72 reviews
Leesburg, FL
25/06 – 29/06
SG$236/nighttotal: SG$944 (4 )
Cute Little Boathouse Escape Bring Your Boat
1 2
apartment , Tavares
This waterfront apartment is situated on the Harris Chain of Lakes, just a short drive from the historic town of Mount Dora and the charming city of Eustis. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. The apartment is a one-bedroom, one-bathroom property that comfortably accommodates up to five guests. Enjoy your stay with direct waterfront access, a private dock, complimentary kayaks, a fenced yard, and a fully equipped kitchen, all within a short distance of local attractions.
Best Leesburg, FL holiday rentals with parking
10 1 review
Leesburg, FL
12/07 – 19/07
SG$215/nighttotal: SG$1505 (7 )
The Palm Tree Pad - 3/2 Home
3 4
apartment , Leesburg
This three-bedroom villa in Okahumpka, The Villages, is situated a short golf cart ride from over 50 golf courses and the entertainment hub of Brownwood Paddock Square. The fully equipped property accommodates up to six guests and includes a complimentary electric golf cart, high-speed Wi-Fi, a fenced backyard, and access to The Villages' recreation centres and pools.
10 20 reviews
Leesburg, FL
12/07 – 19/07
SG$189/nighttotal: SG$1323 (7 )
Casa Bella: 3 Bedroom 2 Bath House Sleeps 6
3 4
apartment , Leesburg
Casa Bella, a newly built home in The Villages, Florida, is situated a short 0.8-kilometre walk from a recreation centre with a swimming pool and various activities, offering easy access to Leesburg's attractions. This 139-square-metre property features three bedrooms, two bathrooms, a spacious open-plan living area, a private lanai with a propane BBQ, and access to over 60 community pools and 20 recreation centres offering activities such as pickleball, tennis, and golf.
Leesburg, FL
12/07 – 19/07
SG$209/nighttotal: SG$1463 (7 )
Near Sawgrass Grove In The Village Of Newell
1 4
house , Leesburg
This detached house in The Village of Newell, near Sawgrass Grove, is located within 37 kilometres of the Lake County Historical Museum, Palisades Golf Club, and Presidents Hall of Fame, and 82 kilometres from Orlando International Airport. This 135 square metre residence offers accommodation for up to seven guests across three bedrooms, featuring a private balcony, a garden, and a fully equipped kitchen with a dishwasher and oven, with free private parking available.
Leesburg, FL
12/07 – 15/07
SG$307/nighttotal: SG$921 (3 )
Paradise On Lake Harris Apt #102
1 4
apartment , Leesburg
Paradise on Lake Harris Apt #102 is located in Leesburg, just 16km from Mount Dora and 24km from Eustis, offering easy access to historical museums, parks, and shopping centres. This apartment has received excellent ratings for location, cleanliness, and user experience. The apartment has one bedroom, one bathroom, and a floor area of 57 square metres, comfortably accommodating up to four guests. It features a fully equipped kitchen, air conditioning, private parking, a garden, and a washing machine, as well as stunning lake views and access to water activities.
Frequently asked questions about holiday rentals in Leesburg, FL
When is the best time to book a vacation rental in Leesburg, FL?
The best time to book a vacation rental in Leesburg is during the spring and autumn, when the weather is mild and the crowds are smaller. If you can, try to book a few months in advance, especially if you're travelling during peak season.
What are the best Airbnb and vacation rentals in Leesburg, FL?
What events or festivals should visitors check out in and around Leesburg, FL?
The Leesburg Bike Fest is a big event in the spring, and the Leesburg Arts Festival is a popular event in the autumn. There are also a number of smaller events and festivals throughout the year, so check the local calendar for details.
What are the most popular Airbnbs in Leesburg, FL?
What are the best budget-friendly activities in Leesburg, FL?
There are plenty of free things to do in Leesburg, like walking around the Venetian Gardens, exploring the historic downtown area, or visiting the Leesburg Heritage Museum. You can also have a picnic in one of the many parks or go for a swim in Lake Griffin.
What are the best vacation rentals with a pool in Leesburg, FL?
What are the best restaurants with local dishes in Leesburg, FL?
For a taste of local flavour, try the Leesburg Farmers Market for fresh produce and local crafts. For a sit-down meal, The Brownwood Hotel has a great restaurant with a menu featuring local ingredients. And if you're looking for something casual, The Gator Dock Restaurant is a popular spot for seafood.
What are the best rentals for families and kids in Leesburg, FL?
What are the best walking or cycling routes in Leesburg, FL?
The Venetian Gardens are a great place for a leisurely walk or bike ride, and there's also a paved trail that runs along the shore of Lake Griffin. For a longer ride, you can head out to the Leesburg Bike Trail, which is a 10 km loop that winds through the countryside.
What are the best rentals or Airbnbs with a jacuzzi in Leesburg, FL?
Are there pet-friendly attractions in Leesburg, FL?
Yes, there are a few pet-friendly attractions in Leesburg. The Venetian Gardens are a great place to walk your dog, and there are also a number of restaurants that have outdoor seating where you can bring your furry friend.
This Creekside Cabanas holiday home in The Villages is located a short walk from Lake Sumter Landing Market Square, offering easy access to shops, restaurants, and evening entertainment. The 149 square metre property boasts a three-bedroom, two-bathroom layout sleeping six, featuring a fully equipped kitchen, private pool, tennis court, screened lanai with BBQ, and a provided golf cart and bicycles for exploring the area.
This Wildwood holiday home in The Villages is situated approximately 1.6km from Lake Deaton, and within 9.6km of both Lake Okahumpka Park and Cane Garden Country Club. This three-bedroom, two-bathroom property offers 171 square metres of living space, accommodating up to six guests and boasting a swimming pool, tennis court, barbecue grills, and free Wi-Fi, plus in-unit laundry facilities.
8.8 905 reviews
Leesburg, FL
12/07 – 19/07
SG$211/nighttotal: SG$1477 (7 )
Mission Resort And Club
1 4
resort , Howey-in-the-Hills
Mission Inn Resort & Club is located in Howey-in-the-Hills, just 10km from Lake Dora and 19km from Eustis Village Shopping Centre and Lakeridge Winery. It has a very good user rating, an excellent location rating and a very good cleanliness rating. The resort is set on a lake and offers a range of amenities and activities, including a golf course, a full-service spa, multiple restaurants, a swimming pool, a jacuzzi, tennis courts, and a fitness centre.
Leesburg, FL
01/08 – 30/09
SG$136/nighttotal: SG$8160 (60 )
Patio Villa W Golf Cart Close To Lake Sumter Landing
1 1
house , The Villages
This patio villa is located in The Villages, offering convenient access to Lake Sumter Landing and attractions such as the Lake County Historical Museum, 37 kilometres away, and Silver Springs, 39 kilometres away. This one-bedroom holiday home accommodates up to seven guests and features air conditioning, a kitchen, complimentary WiFi, free private parking, and a terrace for outdoor enjoyment.
Best pet friendly Leesburg, FL holiday rentals
Among the 252 accommodations in Leesburg, FL, here are the 4 best pet friendly rentals
Leesburg, FL
12/07 – 19/07
SG$170/nighttotal: SG$1190 (7 )
3-2 Patio Villa Best Value
3 4
house , Leesburg
This Leesburg patio villa is conveniently located approximately 30-37 kilometres from various museums and golf clubs. The 56-square-metre property offers two bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, free Wi-Fi, a washing machine, and a golf cart.
8.0 1 review
Leesburg, FL
01/01 – 31/03
SG$213/nighttotal: SG$18957 (89 )
Lakefront Retreat • Patio + Grill • Pet Friendly
2 2
house , Leesburg
This lakefront holiday home in Leesburg is situated 19 kilometres from the Lake County Historical Museum and within 24-29 kilometres of other local historical sites. This spacious 2-bedroom, 2-bathroom holiday let, accommodating up to 7 guests, features a patio with a grill, complimentary private parking, free WiFi, and is pet-friendly.
9.8 47 reviews
Leesburg, FL
25/06 – 29/06
SG$294/nighttotal: SG$1176 (4 )
Walk To Lake Sumter Landing! Golf Cart Included!
2 2
apartment , The Villages
This holiday home is located in Virginia Trace, a short distance from The Villages Market Square and Cane Garden Country Club. It has received excellent ratings from previous guests. The property offers two bedrooms and two bathrooms, spread over 107 square metres, comfortably accommodating up to four guests. Enjoy a range of amenities, including a private pool, spa, tennis court, and a fully equipped kitchen, perfect for relaxing and entertaining.
9.9 57 reviews
Leesburg, FL
25/06 – 29/06
SG$236/nighttotal: SG$944 (4 )
Cabin By The Water Escape Bring Your Boat
1 2
cabin , Tavares
This charming lakeside cottage is situated just outside Tavares, a short 5km drive from the historic town of Mount Dora and 10km from Eustis. The property has received excellent ratings for its location, cleanliness, and overall guest experience. The cottage has one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy a fully equipped kitchen, a private bonfire area, and complimentary kayaks and fishing poles for exploring the nearby chain of lakes.