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297 Rentals and Airbnb in Leesburg, FL

Palm Tree Pad | New 3br | Sawgrass | Golf Cart - Leesburg, FL
10 30 reviews
Leesburg, FL
4 3
$283/nighttotal: $1132 (4 )

Palm Tree Pad | New 3br | Sawgrass | Golf Cart

apartment - Leesburg
This three-bedroom, two-bathroom villa is located in The Villages, Florida, a short distance from Southern Oaks and Jubilee golf courses and Brownwood Paddock Square.
The 3-bedroom property offers an open-plan layout, sleeping up to six guests, with a fully equipped kitchen, free Wi-Fi, Netflix, a private garden, swimming pool, parking for two cars and a garage for golf cart storage; an electric golf cart is included.
2 Bedroom Courtyard     Golf Cart              Great Location The Villages Fl - Leesburg, FL
8.8 5 reviews
Leesburg, FL
2 2
$230/nighttotal: $20930 (91 )

2 Bedroom Courtyard Golf Cart Great Location The Villages Fl

house - The Villages
This two-bedroom villa is situated in the St. James district of The Villages, just 13 kilometres from The Villages Market Square and 23 kilometres from Spanish Springs Town Square.
The 113 square metre property features a fully equipped kitchen, air conditioning, a swimming pool and parking, comfortably accommodating up to four guests.
Paradise On Lake Harris Apt #102 - Leesburg, FL
9.9 28 reviews
Leesburg, FL
2 1
$277/nighttotal: $1939 (7 )

Paradise On Lake Harris Apt #102

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.
Perfect Villages Villa Close To The Highway! 2 Person Golf Cart Included! - Leesburg, FL
Leesburg, FL
2 2
$230/nighttotal: $4140 (18 )

Perfect Villages Villa Close To The Highway! 2 Person Golf Cart Included!

apartment - Leesburg
This two-bedroom flat in Okahumpka is centrally located between Sawgrass and Eastport town squares, offering a 64-kilometre drive to Disney parks and proximity to the Paul P. Williams Auditorium and Lake County Historical Museum.
This accommodation sleeps four guests and features two bathrooms, air conditioning, a swimming pool, balcony, and parking, with access to walking/biking trails and golf courses at Plantation Golf Club and Shallow Creek Country Club.
Phifers Paradise Cozy Cottage (Newell) - Leesburg, FL
10 4 reviews
Leesburg, FL
2 2
$184/nighttotal: $1288 (7 )

Phifers Paradise Cozy Cottage (Newell)

apartment - Leesburg
Phifer's Paradise, a dog-friendly cottage in the Village of Newell within The Villages, Florida, is a short walk from Mickylee Pitch & Putt and offers easy access to numerous golf courses and amenities such as Sawgrass Grove.
This two-bedroom, two-bathroom apartment sleeps four, features a fully equipped kitchen with dishwasher, air conditioning, parking, and a comfortable living room with a flat-screen TV, providing easy access to Central Florida attractions via the Florida Turnpike.
Dirty Dog Barndominium - Leesburg, FL
9.8 66 reviews
Leesburg, FL
4 2
$227/nighttotal: $908 (4 )

Dirty Dog Barndominium

farm - Leesburg
Dirty Dog Organic Farm offers rustic barndominium accommodation near Leesburg, a 16km drive from the town centre, providing a tranquil rural escape.
This two-bedroom property sleeps seven, features a kitchen with fridge, freezer and microwave, plus Wi-Fi, air conditioning, parking and allows pets; guests can enjoy farm activities like collecting eggs and feeding the pig.
Waterfront Cottage On The Harris Chain In Leesburg - Leesburg, FL
9.8 228 reviews
Leesburg, FL
2 2
$189/nighttotal: $3402 (18 )

Waterfront Cottage On The Harris Chain In Leesburg

apartment - Lisbon
This charming cottage is situated just 3 kilometres from the Emeralda Marsh Conservation Area, Bell Hammock, and Big Hammock, offering easy access to nature trails and outdoor activities. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
The cottage is perfect for families, with space for up to 4 guests in its one bedroom and one bathroom. Guests can enjoy a range of amenities, including a fully equipped kitchen, a terrace, a jacuzzi, and a fireplace, offering a comfortable and relaxing stay.
3-2 Patio Villa Best Value - Leesburg, FL
Leesburg, FL
4 3
$282/nighttotal: $1128 (4 )

3-2 Patio Villa Best Value

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.
Luxury Home With A Pool And 3 Bedroom - Leesburg, FL
9.8 53 reviews
Leesburg, FL
4 3
$384/nighttotal: $1536 (4 )

Luxury Home With A Pool And 3 Bedroom

apartment - Leesburg
This waterfront house in Leesburg sits on a freshwater canal with direct access to Lake Griffin, just a short distance from shops, restaurants and major roads. The property has received excellent ratings for location, cleanliness and user experience.
The house is spacious and comfortable, with three bedrooms and one bathroom, accommodating up to eight guests. The property features a kitchen with a fridge, freezer, microwave oven and dishwasher, as well as a swimming pool, garden, air conditioning, parking and internet access.
The Palm Tree Pad - 3/2 Home - Leesburg, FL
10 1 review
Leesburg, FL
4 3
$310/nighttotal: $1240 (4 )

The Palm Tree Pad - 3/2 Home

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.
Draper Villa Getaway (Lake Denham) - Leesburg, FL
10 6 reviews
Leesburg, FL
2 2
$215/nighttotal: $19565 (91 )

Draper Villa Getaway (Lake Denham)

apartment - Leesburg
Draper Villa Getaway, a two-bedroom house in the Village of Lake Denham within The Villages, Florida, is conveniently located near Dabney Recreation Centre and a short drive (approximately 16km) from Leesburg.
This self-catering property offers a fully equipped kitchen, in-home laundry, screened lanai, and sleeps four guests, with easy access to multiple recreation centres featuring pools, pickleball, and bocce; Sawgrass Grove and Eastport are also nearby for dining and shopping.
Sleek Tavares Condo 3 Miles To Downtown - Leesburg, FL
8.8 30 reviews
Leesburg, FL
2 2
$210/nighttotal: $19110 (91 )

Sleek Tavares Condo 3 Miles To Downtown

apartment - Tavares
This apartment in Tavares is situated just 1.8 kilometres from Lake Dora and within a 5 kilometre radius of Dora Canal Plaza Shopping Center, Lake County Historical Museum, Wooten Park, and TableTop Team Trivia, offering easy access to local attractions and amenities. It has received excellent user ratings, indicating a comfortable and enjoyable stay.
The two-bedroom apartment spans 111 square metres and can comfortably accommodate up to four guests. It features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as a washing machine, air conditioning, parking, internet access, and two bathrooms for added convenience.

Best family friendly Leesburg, FL vacation rentals

Among the 297 accommodations in Leesburg, FL, here are the 4 best family friendly rentals

Lovely 2br Near Lake Sumter And Brownwood With Golfcart - Leesburg, FL
8.0 1 review
Leesburg, FL
4 1
$290/nighttotal: $1160 (4 )

Lovely 2br Near Lake Sumter And Brownwood With Golfcart

house - The Villages
This 1-bedroom holiday home is located in The Villages, 32 kilometres from the Lake County Historical Museum and 37 kilometres from Eustis Square Shopping Centre, offering golf cart accessibility and proximity to Lake Sumter and Brownwood.
This family-friendly bungalow provides accommodation for up to 7 guests with air conditioning, a fully equipped kitchen including a microwave oven and dishwasher, free WiFi, a swimming pool, garden, and free private parking.
Salty Heron - 2/2 W/ Grill In The Villages - Village Of Lynnhaven - Leesburg, FL
Leesburg, FL
2 2
$356/nighttotal: $2492 (7 )

Salty Heron - 2/2 W/ Grill In The Villages - Village Of Lynnhaven

apartment - Leesburg
This two-bedroom, two-bathroom coastal charm retreat is located in The Village of Lynnhaven, Leesburg, 1.9 kilometres from the Franklin Recreation Centre and Mickylee Pitch & Putt Executive Golf Course, with Sawgrass Grove and Eastport Town Square approximately 5.5 and 8.9 kilometres away respectively.
This 117 square metre flat accommodates up to four guests and features a fully equipped kitchen, a master bedroom with a King Nectar Luxury Mattress, and a guest bedroom with a Queen Nectar Luxury Mattress, with golf cart hire available nearby for exploring The Villages.
Get Cozy In This Renovated Home By The Villages - Leesburg, FL
10 1 review
Leesburg, FL
4 1
$240/nighttotal: $960 (4 )

Get Cozy In This Renovated Home By The Villages

house - Lady Lake
This renovated house in Lady Lake, Florida, is conveniently located approximately 40 kilometres from Ferran Park, the Mount Dora Historical Society Museum, and the Lake County Historical Museum.
This 142-square-metre property boasts one bedroom, two bathrooms, and sleeps up to 19 guests, offering free Wi-Fi, a fully equipped kitchen, and private parking; nearby attractions include Mount Dora and Eustis.
The Howey Mansion Gardener's Cottage - Leesburg, FL
8.6 17 reviews
Leesburg, FL
2 1
$548/nighttotal: $49868 (91 )

The Howey Mansion Gardener's Cottage

house - Howey-in-the-Hills
The Gardener's Cottage is situated on the grounds of the historic Howey Mansion, just a short distance from the centre of Howey-in-the-Hills. This charming cottage has received very good ratings for its location, cleanliness, and overall experience.
The cottage offers a comfortable living space with a separate dining room, bedroom, and bathroom, comfortably accommodating up to 4 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking, while guests can also enjoy access to the Howey Mansion tours and the beautiful botanical gardens.

Best Leesburg, FL vacation rentals with parking

Modern Cottage In The Heart Of Leesburg - Leesburg, FL
9.5 45 reviews
Leesburg, FL
4 2
$217/nighttotal: $868 (4 )

Modern Cottage In The Heart Of Leesburg

apartment - Leesburg
This charming cottage is situated in a central location in Leesburg, just a few kilometres from the town centre and 15-20 kilometres from the popular shopping and dining district of The Villages.
The cottage offers two bedrooms and a bathroom, comfortably sleeping up to four guests. Guests can enjoy a spacious garden with a deck, barbecue grill, and fire pit, perfect for relaxing evenings or al fresco dining.
Tropical Oasis In Pennecamp - Leesburg, FL
10 11 reviews
Leesburg, FL
2 3
$234/nighttotal: $1638 (7 )

Tropical Oasis In Pennecamp

apartment - The Villages
This Pennecamp holiday home in The Villages is situated 2.4 kilometres from Cane Garden Country Club and within 9.6 kilometres of The Villages Market Square and Lake Deaton.
This four-bedroom, two-bathroom property offers 157 square metres of living space, sleeping up to six guests and boasting a private swimming pool, garden, and on-site laundry facilities.
Sugar Oaks Retreat - Leesburg, FL
Leesburg, FL
4 3
$191/nighttotal: $764 (4 )

Sugar Oaks Retreat

apartment - Leesburg
This private country retreat in Leesburg, Florida, offers a tranquil escape with convenient access to the Harris Chain of Lakes, just under 1 kilometre away, and is also within easy reach of The Villages, Mount Dora, and Wildwood.
This pet-friendly flat, boasting 3 bedrooms and 2 bathrooms to accommodate up to 10 guests, features a fenced garden, ample parking suitable for trailers and motorcycles, and a well-equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning and Wi-Fi.
Lakefront Magic Wilderness Cabin - Leesburg, FL
10 27 reviews
Leesburg, FL
4 1
$331/nighttotal: $1324 (4 )

Lakefront Magic Wilderness Cabin

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.

Frequently Asked Questions about vacation rentals in Leesburg, FL

  • What are the top family-friendly attractions in Leesburg, FL?

    The Venetian Gardens is a great place to take the kids, with its beautiful gardens, fountains, and a playground. And if you're looking for some adventure, the Leesburg Recreation Department offers a range of activities for all ages.
  • What are the best Airbnb and vacation rentals in Leesburg, FL?

    Silver Lake Guest Pool House, Cozy Corner ~ Close To The Villages And Disney and Cypress Point Cottage are the most popular Airbnb and vacation rentals in Leesburg, FL among travelers.

  • 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 or autumn months. The weather is perfect for outdoor activities and the crowds are smaller. You'll also find that prices are generally lower during these seasons.
  • What are the most popular Airbnbs in Leesburg, FL?

    Among the Airbnbs in Leesburg, FL, Silver Lake Guest Pool House, Cozy Corner ~ Close To The Villages And Disney and Cypress Point Cottage are the most popular ones.

  • What events or festivals should visitors check out in and around Leesburg, FL?

    The Leesburg Bike Fest is a popular event that takes place every year in April, and the Leesburg Arts Festival is a great way to experience the local art scene. There's also the annual Leesburg International Festival in October.
  • What are the best vacation rentals with a pool in Leesburg, FL?

  • What are the best budget-friendly activities in Leesburg, FL?

    You can enjoy a picnic at Venetian Gardens or take a stroll along the scenic Lake Harris Trail. The Leesburg Public Library also offers a variety of free programs and events.
  • What are the best rentals for families and kids in Leesburg, FL?

  • What are the best restaurants with local dishes in Leesburg, FL?

    The Brownwood Hotel is a great place to try some local cuisine, and if you're looking for a more casual dining experience, the Gator Dock Restaurant is a popular spot known for its seafood.
  • What are the best rentals or Airbnbs with a jacuzzi in Leesburg, FL?

  • What are the best walking or cycling routes in Leesburg, FL?

    The Leesburg Bike Trail is a great option for cyclists, and the Lake Harris Trail offers stunning views of the lake for walkers. There's also a nice loop around the Venetian Gardens.
  • Are there pet-friendly attractions in Leesburg, FL?

    The Venetian Gardens is pet-friendly and has a designated dog park. Many of the restaurants in Leesburg also have outdoor seating that is pet-friendly.
  • What are the top sports attractions and facilities in Leesburg, FL?

    Leesburg has a great sports scene, with the Leesburg Recreation Department offering a variety of activities, including swimming, tennis, and golf. The Leesburg International Airport also hosts a number of sporting events throughout the year.

Popular destinations

Best Leesburg, FL vacation rentals with a balcony

The Golden Palm Mins To Middleton & Eastport Sq. - Leesburg, FL
Leesburg, FL
2 3
$203/nighttotal: $1421 (7 )

The Golden Palm Mins To Middleton & Eastport Sq.

apartment - Wildwood
This three-bedroom flat, situated centrally in The Villages, Wildwood, is a mere 5-minute golf cart ride from Middleton, offering convenient access to numerous golf courses, recreation centres, shopping, and dining.
This property accommodates up to six guests and features a fully equipped kitchen, a screened-in lanai, and access to The Villages' amenities, including neighbourhood pools and pickleball courts.
Cozy 2br Near Eastport Sq. & Middleton | Patio - Leesburg, FL
10 1 review
Leesburg, FL
2 2
$231/nighttotal: $21021 (91 )

Cozy 2br Near Eastport Sq. & Middleton | Patio

apartment - Wildwood
This two-bedroom flat in The Villages is located 800 meters from Eastport Town Square, 1.1 kilometres from Middleton, and 640 meters from Saluki Recreation, providing convenient access to shopping, dining, and entertainment. This fully furnished property accommodates up to six guests and features two en-suite bathrooms, a fully equipped kitchen, air conditioning, a screened lanai, and parking, with guest passes available for the numerous local amenities including over 110 swimming pools and 50 golf courses.
Villages Escape By Eastport Square With Golf Cart And Bbq - Leesburg, FL
10 1 review
Leesburg, FL
2 1
$390/nighttotal: $7020 (18 )

Villages Escape By Eastport Square With Golf Cart And Bbq

house - Wildwood
This spacious holiday home is situated in Sumterville, Florida, 82 kilometres from Orlando International Airport and within driving distance of attractions such as the Lake County Historical Museum (35 kilometres).
This family-friendly property offers accommodation for 11 guests across 158 square metres, featuring a fully equipped kitchen, air conditioning, a year-round outdoor swimming pool, a garden, tennis court, and parking, with a golf cart available for exploring the local area.
-Arbor Grand Estate- - Leesburg, FL
9.4 3 reviews
Leesburg, FL
2 6
$2049/nighttotal: $36882 (18 )

-Arbor Grand Estate-

apartment - Silver Lake
This expansive 6-bedroom, 4-bathroom holiday home in Leesburg, Central Florida, offers a private resort-style retreat located approximately 160 kilometres from Orlando's theme parks and airport, with convenient access to state parks and natural springs.
This pet-friendly, family-friendly property accommodates up to 14 guests and boasts a private swimming pool, a full home gym, dual entertainment areas, an upstairs bar, a multi-sport court, a gazebo with a fire pit, and includes a golf cart, e-bike, and bicycles for exploring the surrounding 20-hectare estate, which is a secure, gated sanctuary.

Best pet friendly Leesburg, FL vacation rentals

Among the 297 accommodations in Leesburg, FL, here are the 4 best pet friendly rentals

Cute Little Canal Front Apartment-bring Your Boat! - Leesburg, FL
9.0 2 reviews
Leesburg, FL
2 1
$157/nighttotal: $14287 (91 )

Cute Little Canal Front Apartment-bring Your Boat!

apartment - Tavares
This canal-front flat in Tavares provides direct access to the Chain of Lakes, including Lake Harris, perfect for boaters and nature lovers.
This pet-friendly accommodation offers complimentary boat docking, bikes, and fishing poles, with truck and boat-trailer parking available for up to two guests.
Joseph`s Oasis At Dabney Near Sawgrass, Eastport And Nature Trails - Leesburg, FL
Leesburg, FL
2 3
$213/nighttotal: $1491 (7 )

Joseph`s Oasis At Dabney Near Sawgrass, Eastport And Nature Trails

apartment - Leesburg
This three-bedroom, two-bathroom holiday let in The Village of Dabney, Leesburg, offers convenient golf cart access to Sawgrass Grove, located just minutes away, and Eastport, approximately 10 kilometres distant.
This well-equipped property accommodates up to six guests, featuring a fully fitted kitchen, air conditioning, a swimming pool, a spa, a garden, and a complimentary golf cart for exploring The Villages' extensive network of paths and nearby recreation centres.
Beautiful 2 Bedroom Home In The Villages! - Leesburg, FL
10 15 reviews
Leesburg, FL
4 2
$240/nighttotal: $960 (4 )

Beautiful 2 Bedroom Home In The Villages!

apartment - Leesburg
This two-bedroom, two-bathroom villa is situated in Dabney Village within The Villages, Florida, less than 10 minutes by golf cart from Franklin Recreation Centre and across from Dabney Recreation Centre, offering easy access to multiple golf courses and walking trails.
The self-catering property sleeps four guests and includes a fully equipped kitchen, washer-dryer, smart TVs, screened lanai, outdoor patio, and a free eBike for exploring the local area, plus free golf cart access and use of various golf courses.
Where Every Day Feels Like A Florida Getaway! - Leesburg, FL
9.2 9 reviews
Leesburg, FL
2 2
$190/nighttotal: $1330 (7 )

Where Every Day Feels Like A Florida Getaway!

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.
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