Holiday Rentals in Leesburg, FL

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Leesburg, FL holiday rentals
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252 Holiday rentals and Airbnb in Leesburg, FL

Best family friendly Leesburg, FL holiday rentals

Among the 252 accommodations in Leesburg, FL, here are the 4 best family friendly rentals

New 2025 Villa With Golf Cart Near Saluki & Eastport - Leesburg, FL
Leesburg, FL
12/07 – 15/07
162 €/nighttotal: 486 € (3 )

New 2025 Villa With Golf Cart Near Saluki & Eastport

2 4
house , Wildwood
This brand new 2025 villa in Sumterville is located approximately 35 to 84 kilometres from golf clubs like Palisades Golf Club and Bella Collina Golf Club, and 35 to 43 kilometres from attractions such as the Lake County Historical Museum and Ferran Park.
This family-friendly property offers 10 square metres of living space, accommodating up to 7 guests with 2 bedrooms, 1 bathroom, air conditioning, a fully equipped kitchen, swimming pool, and complimentary high-speed Wi-Fi and private parking.
Cozy 2br Mins To Lake Sumter Landing And Brownwood Paddock Square With Bbq, Workspace, Murphy Bed - Leesburg, FL
9.0 2 reviews
Leesburg, FL
12/07 – 19/07
133 €/nighttotal: 931 € (7 )

Cozy 2br Mins To Lake Sumter Landing And Brownwood Paddock Square With Bbq, Workspace, Murphy Bed

2 4
house , The Villages
This 1000 square metre detached house is located in The Villages, providing easy access to Lake Sumter Landing and Brownwood Paddock Square, with the Lake County Historical Museum 32 kilometres away.
This property offers accommodation for up to 11 guests, featuring two bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a terrace, parking, and a dedicated workspace with a Murphy bed for flexible sleeping arrangements.
Courtyard Villa W/ Lanai & Community Amenities! - Leesburg, FL
9.4 16 reviews
Leesburg, FL
01/08 – 30/09
117 €/nighttotal: 7020 € (60 )

Courtyard Villa W/ Lanai & Community Amenities!

2 1
house , The Villages
This two-bedroom villa is located in Bonita, The Villages, just over two miles from Cane Garden Country Club and The Villages Market Square, and within six miles of Lake Deaton and Spanish Springs Town Square. The property has received excellent user ratings, making it a popular choice for travellers visiting The Villages.
The 111 square metre villa comfortably accommodates up to four guests, with a fully equipped kitchen, two bathrooms, and a private patio. Guests can enjoy a range of amenities, including a swimming pool, a tennis court, a spa, and a garden, as well as a barbecue grill for al fresco dining.
Charming Courtyard Villa In The Villages - Leesburg, FL
10 1 review
Leesburg, FL
01/08 – 30/09
110 €/nighttotal: 6600 € (60 )

Charming Courtyard Villa In The Villages

3 1
house , Wildwood
This Wildwood villa, situated approximately 32 kilometres from the Lake County Historical Museum and 37 kilometres from the Eustis Square Shopping Centre, offers convenient access to local historical sites and amenities.
The 140-square-metre property boasts three bedrooms, two bathrooms, sleeps up to eleven guests, and includes a swimming pool, fitness centre, and free Wi-Fi; nearby activities include golfing and canoeing.

Best Leesburg, FL holiday rentals with parking

Best Of The Villages!  2br/2ba Home & Amenity Acce - Leesburg, FL
9.6 22 reviews
Leesburg, FL
12/07 – 19/07
139 €/nighttotal: 973 € (7 )

Best Of The Villages! 2br/2ba Home & Amenity Acce

2 4
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.
Charming Rental In The Village Of Pinellas: Your Florida Oasis Awaits - Leesburg, FL
9.8 10 reviews
Leesburg, FL
27/06 – 04/07
125 €/nighttotal: 875 € (7 )

Charming Rental In The Village Of Pinellas: Your Florida Oasis Awaits

2 2
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.
Shantiniketan B 10 /2110 / 50 Minutes To The Disney 2 Mile To Down Town Tavares. - Leesburg, FL
9.6 30 reviews
Leesburg, FL
12/07 – 19/07
113 €/nighttotal: 791 € (7 )

Shantiniketan B 10 /2110 / 50 Minutes To The Disney 2 Mile To Down Town Tavares.

2 4
apartment , Tavares
This Tavares condo is situated approximately 5km from Lake Dora, Dora Canal Plaza Shopping Centre, and the Lake County Historical Museum, offering easy access to local attractions.
The 111 square metre self-catering apartment sleeps four guests and features two bedrooms, two bathrooms, a full kitchen with appliances including a dishwasher, in-unit laundry, and a Smart TV.
Village Of Charlotte Retreat: 3br, 2ba Home, Golf Cart, & Dog-friendly Bliss - Leesburg, FL
9.6 13 reviews
Leesburg, FL
27/06 – 27/07
82 €/nighttotal: 2460 € (30 )

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.

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 or autumn. The weather is perfect for outdoor activities, and the crowds are smaller than during the summer.
  • What are the best Airbnb and holiday rentals in Leesburg, FL?

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

    You can enjoy a free walk around the Leesburg Waterfront Park, which has beautiful views of Lake Harris. Or, you can visit the Leesburg Public Library, which is a great place to relax and read a book.
  • 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 are the best restaurants with local dishes in Leesburg, FL?

    For local dishes, you have to try the seafood at The Fish House. It's a bit of a drive, but it's worth it. Another great option is The Plantation House, which serves up Southern comfort food.
  • What are the best holiday rentals with a pool in Leesburg, FL?

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

    The Leesburg Bike Trail is a great option for both walking and cycling. It's a paved trail that runs along the waterfront and through some beautiful parks. You can also check out the Leesburg Heritage Trail, which is a shorter trail that goes through the historic downtown area.
  • What are the best rentals for families and kids in Leesburg, FL?

  • Are there pet-friendly attractions in Leesburg, FL?

    Leesburg is a very pet-friendly town. Most of the parks are dog-friendly, and there are a few restaurants that have outdoor seating for dogs. The Leesburg Animal Park is a great option for a day out with your furry friend.
  • What are the best rentals or Airbnbs with a jacuzzi in Leesburg, FL?

  • What are the benefits of choosing a vacation rental in Leesburg, FL?

    Vacation rentals offer more space and privacy than hotels, and they're often more affordable. You can also find rentals that are pet-friendly, which is great if you're travelling with your furry friend.
  • What are the top sports attractions and facilities in Leesburg, FL?

    Leesburg has a few great sports facilities, including the Venetian Gardens Recreation Complex, which has a baseball field, basketball court, and tennis courts. You can also check out the Leesburg Golf Course, which is a public course that's open to everyone.

Destinations nearby

Best Leesburg, FL holiday rentals with a balcony

Beautifully Decorated 3 Bdrm Home W/open Floor Plan, Bbq & Wifi - Leesburg, FL
9.6 4 reviews
Leesburg, FL
27/06 – 04/07
164 €/nighttotal: 1148 € (7 )

Beautifully Decorated 3 Bdrm Home W/open Floor Plan, Bbq & Wifi

3 2
apartment , The Villages
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.
3-bedroom House In The Village Of Shadybrook, Only Minutes From Eastport. - Leesburg, FL
10 3 reviews
Leesburg, FL
25/06 – 29/06
182 €/nighttotal: 728 € (4 )

3-bedroom House In The Village Of Shadybrook, Only Minutes From Eastport.

3 2
apartment , Wildwood
This three-bedroom flat is located in Center Hill, within The Villages, offering convenient access to Brownwood Paddock Square (approximately 5 kilometres away), The Villages Market Square, Lake Griffin State Park, and Dade Battlefield State Park.
This property accommodates up to six guests and features air conditioning, Wi-Fi, a swimming pool, and a terrace, with an optional golf cart rental available for exploring nearby attractions such as Leesburg Centre for the Arts.
Recently Updated Beautiful Villa With 4 Seater Gas Golf Cart, Wifi & Bbq!! - Leesburg, FL
9.2 16 reviews
Leesburg, FL
01/08 – 30/09
56 €/nighttotal: 3360 € (60 )

Recently Updated Beautiful Villa With 4 Seater Gas Golf Cart, Wifi & Bbq!!

2 1
apartment , The Villages
This two-bedroom house is situated in Hemingway, just under 5km from Cane Garden Country Club and within 10km of both The Villages Market Square and Lake Deaton.
The 107 square metre property features a fully equipped kitchen, a private pool, a tennis court, and can accommodate up to four guests.
Luxury & Relaxation At This Amazing Pool Home With Golf Cart & Bbq Grill! - Leesburg, FL
9.8 19 reviews
Leesburg, FL
27/06 – 27/07
102 €/nighttotal: 3060 € (30 )

Luxury & Relaxation At This Amazing Pool Home With Golf Cart & Bbq Grill!

3 2
apartment , The Villages
This three-bedroom house is located in Gilchrist, just 3.2 kilometres from Lake Deaton and within 10 kilometres of Cane Garden Country Club, Lake Okahumpka Park, The Villages Market Square, and Miona Lake Golf Club. This smoke-free property offers a private pool, fenced yard, free Wi-Fi, and a fully equipped kitchen, perfect for families or groups of friends travelling together.

Best pet friendly Leesburg, FL holiday rentals

Among the 252 accommodations in Leesburg, FL, here are the 4 best pet friendly rentals

Canal Front Tavares Escape - Leesburg, FL
10 2 reviews
Leesburg, FL
12/07 – 19/07
234 €/nighttotal: 1638 € (7 )

Canal Front Tavares Escape

2 8
apartment , Tavares
This pet-friendly canal-front residence in Tavares offers direct access to local fishing and boating, providing a peaceful escape for up to eight guests.
The entire home, featuring two bedrooms and two bathrooms, includes a private dock, a garden, air conditioning, and a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside on-site internet.
Fully Furnished 2br, 2ba Patio Villa With Golf Cart And High Speed Internet. - Leesburg, FL
10 5 reviews
Leesburg, FL
12/07 – 19/07
146 €/nighttotal: 1022 € (7 )

Fully Furnished 2br, 2ba Patio Villa With Golf Cart And High Speed Internet.

2 4
apartment , Leesburg
This Leesburg holiday home is conveniently located near Plantation Golf Club, Paquette's Historical Farmall Museum, and Lake Harlow Canine Park in Groveland, offering easy access to local attractions.
This two-bedroom, two-bathroom property boasts 120 square metres of floor space, a fully equipped kitchen, a patio, on-site laundry, and a tennis court, accommodating up to four guests.
Charming & Beautifully Decorated Home W/bbq, Golf Cart, & A Bike - Leesburg, FL
9.2 16 reviews
Leesburg, FL
01/08 – 30/09
78 €/nighttotal: 4680 € (60 )

Charming & Beautifully Decorated Home W/bbq, Golf Cart, & A Bike

3 1
apartment , Wildwood
This Wildwood property is conveniently located within a short drive of several attractions including lakes, golf courses, and a historical museum. It has received excellent user ratings, making it a popular choice for travellers.
The three-bedroom house spans 143 square metres, comfortably accommodating up to six guests. It features a fully equipped kitchen, laundry facilities, a barbecue grill, air conditioning, a fitness centre, a tennis court, and free Wi-Fi.
Brand New 2-2 Villa - Leesburg, FL
10 2 reviews
Leesburg, FL
27/06 – 04/07
133 €/nighttotal: 931 € (7 )

Brand New 2-2 Villa

2 2
house , Leesburg
This brand new two-bedroom villa is located in Leesburg, Florida, approximately 26-35 kilometres from attractions including the Lake County Historical Museum, Deer Island Golf Lake Club, and Ferran Park.
The 56 square metre property offers two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen with dishwasher, air conditioning, in-unit laundry, free Wi-Fi, and a complimentary golf cart.
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