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

Designers 3br In The Villages With Four Seaters Golfcart King Bed - Leesburg, FL
10 4 reviews
Leesburg, FL
01/08 – 30/09
116 €/nighttotal: 6960 € (60 )

Designers 3br In The Villages With Four Seaters Golfcart King Bed

3 1
house , Leesburg
The Palm Tree Pad is a family-friendly house located in The Villages, approximately 30 kilometres from the Lake County Historical Museum in Leesburg, offering convenient access to local attractions.
This 134-square-metre property sleeps up to 11 guests and boasts a private pool, spa, tennis court, and fully equipped kitchen; nearby cycling routes and a garden provide further leisure options.
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees - Leesburg, FL
10 18 reviews
Leesburg, FL
01/08 – 30/09
97 €/nighttotal: 5820 € (60 )

Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees

3 1
house , Groveland
This Groveland villa is situated 1.8km from Lakeridge Winery and within 9.6km of Cherry Lake, Ferndale Preserve, Palisades Golf Club, and the Presidents Hall of Fame.
This 33 square metre, three-bedroom property sleeps four guests and boasts a swimming pool, Jacuzzi, fitness centre, and garden, alongside a fully equipped kitchen and free Wi-Fi; enjoy on-site amenities and nearby attractions.
Canal Front Boathouse Escape - Bring Your Boat! - Leesburg, FL
9.8 6 reviews
Leesburg, FL
12/07 – 15/07
163 €/nighttotal: 489 € (3 )

Canal Front Boathouse Escape - Bring Your Boat!

1 4
apartment , Tavares
This houseboat is situated in Tavares, Florida, just a short distance from the historic towns of Mount Dora and Eustis, offering easy access to the Harris Chain of Lakes. It has been highly rated by previous guests, receiving excellent reviews.
The houseboat has one bedroom and one bathroom, comfortably accommodating up to five guests. Amenities include a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, and complimentary kayaks for exploring the lake.
Salty Seahorse - 3/2 W/ Golf Cart & Grill In The Village Of Lake Denham Near Eastport - Leesburg, FL
10 1 review
Leesburg, FL
25/06 – 29/06
226 €/nighttotal: 904 € (4 )

Salty Seahorse - 3/2 W/ Golf Cart & Grill In The Village Of Lake Denham Near Eastport

3 2
apartment , Leesburg
This three-bedroom, two-bathroom home is located in the Village of Lake Denham, Leesburg, offering convenient access to Eastport Town Square, approximately 7.7 kilometres away, and the Florida Turnpike for trips to Orlando and Disney World.
This 159 square metre residence accommodates up to six guests and features a fully equipped kitchen, a screened-in lanai with a fountain, a private patio with a gas grill, and access to numerous community amenities including pools and golf courses, with a golf cart provided for local exploration.

Best Leesburg, FL holiday rentals with parking

Great 3/2 Villages Home With Amenities Access - Leesburg, FL
9.8 34 reviews
Leesburg, FL
12/07 – 15/07
159 €/nighttotal: 477 € (3 )

Great 3/2 Villages Home With Amenities Access

1 4
house , Leesburg
This three-bedroom patio villa is located in the Village of Lake Denham within The Villages, Florida, a short golf cart ride (approximately 1.6 km) from Sawgrass Grove shopping and dining, and Homestead and Franklin Recreation Centres.
The 3-bedroom, 2-bathroom property offers a spacious open-plan layout, sleeping up to six guests, and includes a golf cart, fully equipped kitchen with wine chiller, pool towels, highchair, and Pack 'n Play; nearby amenities include Southern Oaks Golf Club.
Villa W 4 Person Golf Cart 1m To Brownwood Sq-no Xtra Guest Fees. Active Hosts - Leesburg, FL
10 50 reviews
Leesburg, FL
12/07 – 15/07
148 €/nighttotal: 444 € (3 )

Villa W 4 Person Golf Cart 1m To Brownwood Sq-no Xtra Guest Fees. Active Hosts

2 4
apartment , The Villages
This Wildwood holiday home is situated 2.4 kilometres from Lake Deaton and within 9.6 kilometres of Lake Okahumpka Park and Cane Garden Country Club, offering easy access to The Villages' amenities.
This two-bedroom, two-bathroom property sleeps four guests and boasts a private pool, spa, BBQ, smart TV, washing machine, fully equipped kitchen, and is close to various recreational activities.
Free Golf Cart! Fabulous Location! Classy Decor! Pet-friendly! - Leesburg, FL
10 60 reviews
Leesburg, FL
25/06 – 29/06
150 €/nighttotal: 600 € (4 )

Free Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

3 2
apartment , The Villages
This three-bedroom house is located in Winifred, just 3 kilometres from The Villages Market Square and 5 kilometres from Glenview Champions Country Club. It has received excellent reviews from previous guests.
The property can accommodate up to 6 guests and is well-equipped with modern amenities, including a swimming pool, jacuzzi, and barbecue facilities. Guests can enjoy relaxing in the garden or on the terrace, and there is free Wi-Fi throughout the house.
Paradise On Lake Harris Apt #101 - Leesburg, FL
9.2 10 reviews
Leesburg, FL
01/08 – 30/09
104 €/nighttotal: 6240 € (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.

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

Spacious 2br In The Villages, Near Eastport And Pools - Leesburg, FL
Leesburg, FL
01/01 – 31/03
307 €/nighttotal: 27323 € (89 )

Spacious 2br In The Villages, Near Eastport And Pools

2 2
house , Wildwood
This two-bedroom detached house in The Villages, Sumterville, is situated 37 kilometres from the Lake County Historical Museum and 39 kilometres from Palisades Golf Club.
This family-friendly property offers accommodation for up to seven guests, featuring 130 square metres of living space with air conditioning, a fully equipped kitchen, a balcony, and private parking, with a year-round outdoor pool and The Villages' amenities nearby.
Beautiful 2/2 Designer Home Is Located North Of 466a, Near Lake Sumter Landing. - Leesburg, FL
Leesburg, FL
01/01 – 31/03
234 €/nighttotal: 20826 € (89 )

Beautiful 2/2 Designer Home Is Located North Of 466a, Near Lake Sumter Landing.

2 2
apartment , The Villages
This two-bedroom apartment in Pennecamp, The Villages, is situated 1.3km from Lake Sumter Landing and 0.5km from Cane Garden Country Club, offering easy access to local amenities and attractions including Paquette's Historical Farmall Museum.
The 172 square metre self-catering property features an open-plan design with a glass-enclosed lanai, sleeping up to four guests in two queen-sized bedrooms, and includes a fully equipped kitchen, swimming pool access, and parking.
Cozy 2br Mins To Lake Sumter & Sawgrass | Kingbed - Leesburg, FL
Leesburg, FL
12/07 – 15/07
160 €/nighttotal: 480 € (3 )

Cozy 2br Mins To Lake Sumter & Sawgrass | Kingbed

2 4
apartment , The Villages
This two-bedroom flat in Liberty Park offers convenient access to The Villages' main squares and numerous golf courses, located within a 1.1 to 1.6 kilometre drive of Lake Sumter Landing, Brownwood Paddock Square, and Spanish Springs Town Square.
This fully furnished apartment accommodates four guests and features two ensuite bathrooms, a well-equipped kitchen with full-size appliances, air conditioning, a screened-in lanai, and in-unit laundry facilities, with parking available.
Spacious 2br In The Villages! Near Eastport & Pool - Leesburg, FL
Leesburg, FL
01/01 – 31/03
244 €/nighttotal: 21716 € (89 )

Spacious 2br In The Villages! Near Eastport & Pool

2 2
apartment , Wildwood
This two-bedroom flat is situated in Center Hill, Wildwood, offering convenient access to Eastport Town Square, approximately 7 minutes away, and Saluki Recreation, just 4 minutes distant.
This professionally managed accommodation for four guests features a king and two twin beds, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, high-speed Wi-Fi, Netflix, and a screened lanai patio, with access to The Villages' amenities via Lifestyle IDs.

Best pet friendly Leesburg, FL holiday rentals

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

Phifer’s Paradise Cozy Cottage (Newell) - Leesburg, FL
10 3 reviews
Leesburg, FL
05/07 – 31/08
93 €/nighttotal: 5301 € (57 )

Phifer’s Paradise Cozy Cottage (Newell)

2 1
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.
Near Sawgrass Grove In The Village Of Newell - Leesburg, FL
Leesburg, FL
12/07 – 15/07
234 €/nighttotal: 702 € (3 )

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.
Canal Front Tavares Escape - Leesburg, FL
10 2 reviews
Leesburg, FL
01/01 – 31/03
132 €/nighttotal: 11748 € (89 )

Canal Front Tavares Escape

2 2
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.
Near Sawgrass Grove In The Village Of Newell - Leesburg, FL
8.0 5 reviews
Leesburg, FL
01/08 – 30/09
95 €/nighttotal: 5700 € (60 )

Near Sawgrass Grove In The Village Of Newell

3 1
apartment , Leesburg
This pet-friendly apartment in Okahumpka's Village of Newell offers convenient access to Sawgrass Grove and Homestead Recreation Center, situated within a golf cart community approximately 5 kilometres from Leesburg.
This 135 square metre residence accommodates up to six guests with three bedrooms, two bathrooms, a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, terrace, garden, and parking, plus a den with a sleeper sofa.
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