Holiday Rentals in Leesburg, FL

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

Best family friendly Leesburg, FL holiday rentals

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

Venetian Gardens Home In Peaceful Neighborhood - Leesburg, FL
10 17 reviews

Venetian Gardens Home In Peaceful Neighborhood

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.
Family 3br Sleeps 7 | Bunk Room | Fenced Yard - Leesburg, FL
10 3 reviews

Family 3br Sleeps 7 | Bunk Room | Fenced Yard

apartment, Leesburg
This three-bedroom, two-bathroom flat is located in The Villages, Leesburg, providing convenient access to Eastport (approximately 1.6 km away), Sawgrass Grove, and Franklin Recreation Centre.
This spacious 137-square-meter single-level residence accommodates up to seven guests and features an open-concept living area, a fully equipped kitchen with island seating, a primary suite with an en-suite bathroom, a screened lanai overlooking a private garden, in-unit laundry, high-speed Wi-Fi, and a two-car garage, with access to The Villages' amenities including swimming pools and recreation centres for an additional guest lifestyle ID fee.
Spacious 3br - Sleeps 7 - King Bed - Lanai - Leesburg, FL
No reviews

Spacious 3br - Sleeps 7 - King Bed - Lanai

house, Leesburg
This detached house in Okahumpka, Florida, is located approximately 29 kilometres from the Lake County Historical Museum and 34 kilometres from Palisades Golf Club.
This family-friendly holiday home offers 1477 square metres of space, accommodating up to 13 guests with 3 bedrooms and 2 bathrooms, featuring a year-round outdoor swimming pool, a private balcony, a fully equipped kitchen with a dishwasher and microwave, air conditioning, free WiFi, and private on-site parking.
Get Cozy In This Newly Renovated Home By The Villages! - Leesburg, FL
9.8 22 reviews

Get Cozy In This Newly Renovated Home By The Villages!

apartment, Lady Lake
This apartment is situated in the peaceful Spring Arbor Village neighbourhood of Lady Lake, Florida, just a short distance from The Villages' golf courses, restaurants, and entertainment venues. It has received excellent reviews from previous guests.
The property has three bedrooms and two bathrooms, comfortably accommodating up to 11 guests. It offers a fully equipped kitchen, air conditioning, Wi-Fi, parking, and a quiet location for a relaxing stay.

Best Leesburg, FL holiday rentals with parking

Cottage 23, The Lighthouse - Dora Canal Court - A Downtown, Waterfront Community - Leesburg, FL
10 2 reviews

Cottage 23, The Lighthouse - Dora Canal Court - A Downtown, Waterfront Community

house, Tavares
Cottage 23, a waterfront property in the Dora Canal Court area of Tavares, Florida, is situated 53 kilometres from Orlando Sanford International Airport.
This recently renovated one-bedroom house offers 37 square metres of living space, including a fully equipped kitchenette, walk-in shower, sun terrace, and private parking, accommodating two guests and boasting nearby fishing opportunities.
Draper Villa Getaway (Lake Denham) - Leesburg, FL
10 7 reviews

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.
Country Living Close To The Villages. - Leesburg, FL
10 8 reviews

Country Living Close To The Villages.

apartment, Leesburg
This two-bedroom apartment is situated in a peaceful rural setting just outside Leesburg, close to Lake Griffin State Park and Venetian Gardens. The property enjoys excellent guest reviews, with many praising its tranquil location and comfortable amenities.
The apartment has two bathrooms and can comfortably accommodate up to four guests. It features a fully equipped kitchen, a spacious living area, a private garden, a Jacuzzi, and a screened porch, making it perfect for relaxing and enjoying the beautiful surroundings.
Outdoor Oasis W/ Bar & Lanai: Tavares Escape - Leesburg, FL
9.2 7 reviews

Outdoor Oasis W/ Bar & Lanai: Tavares Escape

apartment, Tavares
This three-bedroom holiday let in Tavares is located a mile from Wooton Park and its splash pad, offering convenient access to the Chain O' Lakes and local amenities.
This 140-square-metre holiday home accommodates up to seven guests, featuring a private saltwater pool with a chair lift, a fenced yard with toddler toys, and a screened-in lanai with a gas firepit, all within easy reach of local attractions and conservation areas.

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.

Popular destinations

Best Leesburg, FL holiday rentals with a balcony

Relaxation Meets Recreation - Leesburg, FL
10 1 review

Relaxation Meets Recreation

house, Wildwood
This three-bedroom Wildwood holiday home, situated in Sumterville, is conveniently located within 35-43km of attractions such as the Palisades Golf Club and the Presidents Hall of Fame.
The 149 square metre property boasts a fully equipped kitchen, two bathrooms, a private terrace, swimming pool, and garden; sleeping up to 11 guests and offering complimentary Wi-Fi and private parking.
New 2br The Villages | Golf Cart | Eastport Sq. - Leesburg, FL
No reviews

New 2br The Villages | Golf Cart | Eastport Sq.

house, Wildwood
This Sumterville holiday let is situated between 32 and 37 kilometres from the Lake County Historical Museum, Palisades Golf Club, Presidents Hall of Fame, and Eustis Square Shopping Centre, and offers convenient access to The Villages retirement community.
This family-friendly 130 square metre property accommodates up to seven guests in two bedrooms and two bathrooms, featuring a fully equipped kitchen with a dishwasher and oven, air conditioning, a swimming pool, garden, terrace, balcony, and included golf cart access, with free private parking and Wi-Fi available.
Walk To Saluki Recreational Center, Minnutes To Eastport With Golfcart - Leesburg, FL
No reviews

Walk To Saluki Recreational Center, Minnutes To Eastport With Golfcart

house, Wildwood
This Sumterville holiday cottage is situated near the Saluki Recreational Centre and a short drive from Eastport, with the Lake County Historical Museum and Palisades Golf Club approximately 35-37 kilometres away.
This family-friendly holiday home offers 1200 square meters of living space for up to 7 guests, featuring 2 bedrooms, 2 bathrooms, air conditioning, a swimming pool, a balcony, a garden, and free private parking.
Waterfront Cottage On The Harris Chain In Leesburg - Leesburg, FL
9.8 228 reviews

Waterfront Cottage On The Harris Chain In Leesburg

cottage, 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.

Best pet friendly Leesburg, FL holiday rentals

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

Waterfront Home With Firepit And Foosball Table - Leesburg, FL
9.4 10 reviews

Waterfront Home With Firepit And Foosball Table

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.
Waterfront Cottage On Haynes Creek - Leesburg, FL
9.4 18 reviews

Waterfront Cottage On Haynes Creek

cottage, Lisbon
This charming cottage is located in Leesburg, Florida, just a short drive from the Harris Chain of Lakes and within easy reach of several towns, offering a peaceful retreat from the hustle and bustle of city life. The property has received very good ratings from previous guests.
This cosy dwelling has one bedroom and one bathroom, accommodating up to four guests. It offers a range of amenities including internet, air conditioning, and a private boat slip, as well as access to kayaks, a paddleboat, and a paddleboard for exploring the surrounding waterways.
Beautifully 2/2 Dog-friendly Patio Villa W/golf Cart, Bbq, & Free Wifi! - Leesburg, FL
9.8 12 reviews

Beautifully 2/2 Dog-friendly Patio Villa W/golf Cart, Bbq, & Free Wifi!

apartment, The Villages
This two-bedroom villa in the Village of Hillsborough offers convenient access to The Villages' attractions, being situated less than 1.6 kilometres from Brownwood Paddock Square and a short golf cart journey to the Manatee Recreation Centre.
This dog-friendly accommodation, spanning 107 square metres and accommodating up to four guests, features a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, a swimming pool, a screened-in lanai, a separate grilling area with a gas barbecue, and includes a two-person gas golf cart.
Lakeview With Shuffleboard Table And Wildlife Spotting - Leesburg, FL
No reviews

Lakeview With Shuffleboard Table And Wildlife Spotting

house, Fruitland Park
This holiday home in Fruitland Park is situated 22.5 kilometres from the Lake County Historical Museum and 27.4 kilometres from Eustis Square Shopping Centre.
This spacious 192 square metre property accommodates up to 10 guests, featuring 3 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, a balcony, free WiFi, a garden, table tennis, and a shuffleboard table, with pets welcome.