Best Holiday rentals and Airbnb offers in Leesburg, FL
9.5 13 reviews
Leesburg, FL
27/06 – 27/07
SG$181/nighttotal: SG$5430 (30 )
The Villages-*new* Cozy Vacation Villa
1 2
apartment , Leesburg
This modern, two-bedroom house in The Villages' Lake Denham district, Leesburg, Florida, is situated approximately 72km from Orlando and 160km from Tampa, close to Homestead and Franklin Recreation Centres. The 2-bathroom property, sleeping six with a queen-size sofa bed, boasts a swimming pool, fitness centre, and complimentary access to Villages recreation facilities (request passes at least three days prior); nearby amenities include Sawgrass Grove and McGrady’s Pub.
9.1 73 reviews
Leesburg, FL
25/06 – 29/06
SG$248/nighttotal: SG$992 (4 )
3 Br 2 Bath Home Full Kitchen Pool Boat Parking
3 2
apartment , Leesburg
This holiday home is situated in Leesburg, just under 5km from Lake Griffin, UF Health Leesburg Hospital and Venetian Gardens, offering easy access to local attractions and amenities. The property has received excellent ratings for location, cleanliness and overall experience. The three-bedroom house comfortably accommodates up to eight guests, providing ample space for families or groups of friends. The property features a range of amenities including a private garden, swimming pool, jacuzzi, barbecue grills and free WiFi, ensuring a relaxing and enjoyable stay.
9.2 10 reviews
Leesburg, FL
01/08 – 30/09
SG$154/nighttotal: SG$9240 (60 )
Paradise On Lake Harris Apt #101
2 1
apartment , Leesburg
This Leesburg apartment is situated within 3.2km of UF Health Leesburg Hospital and under 9.7km from Lake Griffin State Park, offering convenient access to local healthcare and outdoor recreation. This two-bedroom, one-bathroom flat sleeps six guests and includes free Wi-Fi, parking, in-unit laundry, and essential amenities such as a hairdryer and iron; nearby attractions include Venetian Gardens, within 3.2km.
10 1 review
Leesburg, FL
01/08 – 30/09
SG$149/nighttotal: SG$8940 (60 )
Paradise On Lake Harris Apt #202
1 1
apartment , Leesburg
This Leesburg apartment is situated within 3.2km of UF Health Leesburg Hospital and Lake Griffin, and within 9.6km of Lake Griffin State Park, offering convenient access to local amenities and attractions. The one-bedroom, one-bathroom flat sleeps four guests and includes in-unit laundry facilities, free Wi-Fi, and a peaceful garden setting within a smoke-free apartment complex.
9.4 10 reviews
Leesburg, FL
01/01 – 31/03
SG$132/nighttotal: SG$11748 (89 )
Waterfront Home With Firepit And Foosball Table
2 2
house , Fruitland Park
This Fruitland Park flat offers direct lake access, situated 10 minutes from The Villages and 7 minutes from Lake Griffin State Park. This pet-friendly apartment accommodates up to six guests with two bedrooms, featuring a king bed and a queen-over-queen bunk, and includes a kitchenette, a screened-in porch, a football table, and a Smart TV.
9.5 8 reviews
Leesburg, FL
01/01 – 31/03
SG$253/nighttotal: SG$22517 (89 )
Walk To Restaurants: Downtown Leesburg Townhome!
3 2
house , Leesburg
This three-bedroom townhouse is located in Leesburg, Central Florida, within an 18-kilometre radius of several golf courses and numerous parks and trails. It has received very good user ratings and excellent ratings for location and cleanliness. The property comfortably sleeps six guests and features a fully equipped kitchen with a dishwasher, a balcony and deck, a smart TV with cable, free Wi-Fi, central air conditioning and heating, step-free entry, a first-floor bedroom, an exterior security camera, and a driveway that accommodates one vehicle.
10 2 reviews
Leesburg, FL
01/08 – 30/09
SG$177/nighttotal: SG$10620 (60 )
Book In "The Villages" For A Fabulous Lifestyle For Either Couples Or Families!
3 1
apartment , Leesburg
This three-bedroom apartment is situated in Okahumpka, just a short drive from Leesburg, next to a golf course and on a lake, offering a peaceful setting with beautiful views. It has received excellent user ratings, indicating a high level of satisfaction from previous guests. The apartment spans 139 square metres and can comfortably accommodate up to four guests. It is equipped with a range of amenities, including a fully equipped kitchen, air conditioning, a swimming pool, a garden, a tennis court, and parking, ensuring a comfortable and enjoyable stay.
10 9 reviews
Leesburg, FL
12/07 – 19/07
SG$398/nighttotal: SG$2786 (7 )
Angler's Landing Near Lake Harris/ Boat Parking
1 8
apartment , Leesburg
This four-bedroom, two-bathroom flat in Leesburg offers immediate access to Lake Harris, Lake Eustis, Lake Dora, and Lake Griffin, with boat ramps located within 800 metres. This family-friendly accommodation for up to eight guests includes private, fenced parking suitable for multiple boats, a garden, and a fully equipped kitchen, making it ideal for fishing expeditions across Central Florida's lakes.
10 2 reviews
Leesburg, FL
01/08 – 30/09
SG$93/nighttotal: SG$5580 (60 )
Charming Home W/spacious Kitchen, Water View, Enclosed Lanai, & Pet Friendly
2 1
apartment , Leesburg
This Village of Newell apartment, situated in Okahumpka near The Villages, offers convenient access to Brownwood Paddock Square and Sawgrass Market Place via a short golf cart ride. This two-bedroom, two-bathroom dwelling boasts 117 square metres of living space, featuring a split floor plan, a private golf cart garage, a swimming pool, and sleeps up to four guests, making it ideal for families or groups of friends visiting Leesburg.
9.6 133 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.
10 4 reviews
Leesburg, FL
27/06 – 27/07
SG$134/nighttotal: SG$4020 (30 )
Next/pitch & Putt, Short Ride/sawgrass, 55m/disney
1 2
house , Leesburg
This brand new, two-bedroom villa in The Villages of Lake Denham, Leesburg, is within walking distance of Mickylee Pitch and Putt and less than 2.4 kilometres from the Homestead Recreation Centre and Ezell Recreation Centre. The 2-bathroom property sleeps four, boasts a fully equipped kitchen, BBQ grill, in-unit laundry, and access to numerous walking trails, swimming pools, tennis courts, and pickleball facilities nearby.
9.8 9 reviews
Leesburg, FL
27/06 – 27/07
SG$116/nighttotal: SG$3480 (30 )
Paradise On Lake Harris Apt #201
1 2
apartment , Leesburg
This Leesburg apartment boasts a prime waterfront location on Lake Harris, just 0.3km from Venetian Gardens and a 3-minute drive from UF Health Leesburg Hospital. The one-bedroom, one-bathroom flat sleeps four, offering a fully furnished interior with modern appliances, a private patio, boat dock access, on-site washer/dryer, and a gas grill, perfect for families or groups exploring the area.
Best family friendly Leesburg, FL holiday rentals
Among the 252 accommodations in Leesburg, FL, here are the 4 best family friendly rentals
9.9 27 reviews
Leesburg, FL
27/06 – 04/07
SG$254/nighttotal: SG$1778 (7 )
Paradise On Lake Harris Apt #102
1 2
apartment , Leesburg
This lakeside flat is located in Leesburg, just a short walk from Venetian Gardens and a 50-kilometre drive from Disney World. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience. The self-catering property is ideal for families or groups of up to four people, featuring a bedroom, a bathroom, and a well-equipped kitchen. Guests can enjoy the private backyard oasis, the fully furnished living space, and the convenience of on-site laundry facilities.
9.6 22 reviews
Leesburg, FL
27/06 – 04/07
SG$229/nighttotal: SG$1603 (7 )
Best Of The Villages! 2br/2ba Home & Amenity Acce
2 2
apartment , Leesburg
This two-bedroom, two-bathroom patio villa is located in the Village of Lake Denham within The Villages, Florida, a short golf cart ride (approximately 1.6km) from Sawgrass Grove shopping and dining. The 4-guest property boasts a spacious open-plan layout, a fully equipped kitchen with stainless steel appliances, and family-friendly amenities including a highchair and Pack 'n' Play, plus access to nearby recreation centres with pools and sports facilities.
9.8 14 reviews
Leesburg, FL
25/06 – 29/06
SG$270/nighttotal: SG$1080 (4 )
Tranquil Central Fl Retreat
3 2
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.
10 108 reviews
Leesburg, FL
27/06 – 04/07
SG$108/nighttotal: SG$756 (7 )
Fully Furnished Brand New Villa In Village Of St. Catherine's With Cart
2 2
house , Wildwood
This two-bedroom property is situated in Wildwood, just 4km from Lake Deaton and Continental Country Club, offering easy access to outdoor activities and recreation. Guests have consistently rated this property as excellent, highlighting its comfortable and convenient features. The villa comfortably accommodates up to six guests and features a well-equipped kitchen, a private patio, beach towels, free Wi-Fi, tennis court access, and a swimming pool. Enjoy the fresh air, relax by the pool, or take advantage of the nearby lake and country club for a day of outdoor fun.
Best Leesburg, FL holiday rentals with parking
Leesburg, FL
01/01 – 31/03
SG$146/nighttotal: SG$12994 (89 )
Cottage 33: Pineapple Place - Waterfront Lodging In Downtown Tavares, Fl
1 2
cottage , Tavares
This Tavares waterfront cottage, situated steps from Dora Canal and within walking distance of Tavares' town centre, offers easy access to Lake County Historical Museum and Paul P. Williams Auditorium. The 22-square-metre (approximately 237-square-foot) self-catering property features one bedroom, one bathroom, and sleeps two, boasting a private spa, air conditioning, assigned parking, and access to a community fish cleaning station and laundromat.
9.2 9 reviews
Leesburg, FL
27/06 – 04/07
SG$177/nighttotal: SG$1239 (7 )
Beautiful 2/2 Dog Friendly Patio Villa W/bbq & Close To Lake Sumter Landing!
2 2
apartment , The Villages
This smoke-free villa is located in Mallory Square, just over 5 kilometres from The Villages Market Square and less than 8 kilometres from Cane Garden Country Club. The 107 square metre property offers two bedrooms, two bathrooms, and can accommodate up to four guests, with amenities including a swimming pool, tennis court, and a fully equipped kitchen.
9.2 23 reviews
Leesburg, FL
27/06 – 04/07
SG$184/nighttotal: SG$1288 (7 )
Blissful Village Bungalow 2br-2ba & Membership Ame
1 2
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.
9.8 10 reviews
Leesburg, FL
01/08 – 30/09
SG$89/nighttotal: SG$5340 (60 )
Charming Rental In The Village Of Pinellas: Your Florida Oasis Awaits
2 1
apartment , The Villages
This two-bedroom villa is located in Wildwood, just 4.2 kilometres from Lake Deaton and within a 10 kilometre radius of several attractions including Lake Okahumpka Park and Cane Garden Country Club. The property has received excellent user ratings and is perfect for a relaxing getaway. The 108 square metre villa comfortably accommodates up to four guests. Enjoy a private setting with a swimming pool, tennis court, and garden, as well as a fully equipped kitchen and free Wi-Fi.
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.
Destinations nearby
Best Leesburg, FL holiday rentals with a balcony
Leesburg, FL
27/06 – 04/07
SG$441/nighttotal: SG$3087 (7 )
Holiday Vacation Rental Home
3 2
apartment , Leesburg
This 3-bedroom holiday flat in Leesburg is located in a secluded area of Holiday RV Village, offering convenient access to ViaPort Florida (approximately 3.5 kilometres away) and Lake Square Mall, as well as proximity to Lake Griffin State Park and Fern Prairie Preserve. This accommodation provides space for up to 8 guests with 3 bedrooms and 3 bathrooms, featuring a private outdoor entertaining area with a pool and spa, alongside access to resort amenities including a marina, fitness centre, and sports courts, with an optional suite available for extra capacity.
Leesburg, FL
27/06 – 04/07
SG$242/nighttotal: SG$1694 (7 )
Charming Large 3-bedroom 2 Bath House In The Villages.
3 2
apartment , The Villages
This 2,200 sq ft flat is located in the Bridgeport district at Lake Miona, offering direct access across the street to Palmer Legends Golf & Country Club and is just minutes from Lake Sumter Landing. This property provides accommodation for six guests across three bedrooms and two bathrooms, featuring a microwave oven, dishwasher, air conditioning, and a terrace, with guest passes for golf included and a golf cart rental option available.
Leesburg, FL
27/06 – 27/07
SG$189/nighttotal: SG$5670 (30 )
Close To Pelican Heron Golf Course And Only 7 Minutes To Lake Sumter Landing
3 2
apartment , The Villages
This three-bedroom apartment is situated in Sunset Pointe, a short distance from the Sunset Pointe Pool & Lake Miona Recreation Centre and just 4.5 kilometres from the central hub of The Villages, Lake Sumter Landing. The 138 square metre property is fully furnished and can accommodate up to six guests, with amenities including a private garden, swimming pool, and a screened-in lanai.
9.8 8 reviews
Leesburg, FL
25/06 – 29/06
SG$718/nighttotal: SG$2872 (4 )
Villages2530-gorgeous Florida Rental !!
3 2
apartment , The Villages
This three-bedroom apartment is located in Hadley, just under 8 kilometres from Lake Deaton and within 10 kilometres of The Villages Market Square, Cane Garden Country Club, Continental Country Club, and Spanish Springs Town Square, offering a peaceful retreat away from the hustle and bustle of the town centres. The property comfortably sleeps eight guests and features a fully equipped kitchen, a private balcony, a swimming pool, and a garden. Guests can enjoy a range of activities including golf, swimming, and exploring the local area.
Best pet friendly Leesburg, FL holiday rentals
Among the 252 accommodations in Leesburg, FL, here are the 4 best pet friendly rentals
9.6 13 reviews
Leesburg, FL
27/06 – 04/07
SG$228/nighttotal: SG$1596 (7 )
Village Of Charlotte Retreat: 3br, 2ba Home, Golf Cart, & Dog-friendly Bliss
3 2
apartment , The Villages
This holiday let is situated in the Village of Charlotte within The Villages, offering convenient access to Brownwood Paddock Park, approximately 1.5 kilometres away, for shopping, dining, and entertainment. This spacious 138 square metre apartment accommodates up to six guests across three bedrooms, featuring a master suite with a king-sized bed and en-suite, two guest rooms with queen beds (one a sofa bed), two bathrooms, a well-equipped kitchen, air conditioning, a swimming pool, a screened lanai with a gas BBQ, and a golf cart for exploring the amenities.
9.9 49 reviews
Leesburg, FL
12/07 – 15/07
SG$363/nighttotal: SG$1089 (3 )
Royal Oak Lakeview Serenity
1 4
apartment , Leesburg
This Leesburg lakeside bungalow, boasting stunning Lake Harris views and private beach access (no dock), is conveniently located near three restaurants within walking distance, with Publix supermarket and further dining options a short 3.2km drive away, and major attractions and The Villages within a 16-32km radius. This renovated 2100 sq ft (195 sq m) three-bedroom, two-bathroom house sleeps eight, features a game room with darts, pool, and ping pong, an outdoor kitchen with pergola, and a covered RV carport (power hookup extra); boat launch ramps are nearby.
10 123 reviews
Leesburg, FL
12/07 – 15/07
SG$201/nighttotal: SG$603 (3 )
Walk To Lake Sumter Landing! Our Village Gem - 10 Star - W/ Golf Cart
2 4
apartment , The Villages
This two-bedroom house is located in Caroline, just 1.3 kilometres from The Villages Market Square and 4.2 kilometres from Cane Garden Country Club, offering a peaceful retreat from the hustle and bustle of the central areas. It has received excellent user ratings, making it a popular choice for travellers. The house spans 119 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, a patio for outdoor enjoyment, a washing machine, and a garden with barbecue facilities, providing everything you need for a relaxing and enjoyable stay.
9.5 4 reviews
Leesburg, FL
12/07 – 19/07
SG$199/nighttotal: SG$1393 (7 )
Near Sawgrass Grove In The Village Of Newell
3 4
apartment , Leesburg
This pet-friendly flat in The Village of Newell offers a peaceful retreat with pastoral views, located a short distance from Leesburg's attractions. Accommodating up to six guests, this residence features three bedrooms, two bathrooms, a den with a sleeper sofa, and a garden, with a kitchen equipped with a fridge, freezer, microwave, and dishwasher.