Holiday Rentals in Leesburg, FL

297 available vacation rental offers

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Leesburg, FL holiday rentals
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Best Holiday rentals and Airbnb offers 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

Black Sheep Hideaway Modern Countryside Serenity - Leesburg, FL
9.7 9 reviews

Black Sheep Hideaway Modern Countryside Serenity

house, Minneola
This Minneola holiday home, situated in Clermont, offers easy access to Orlando's theme parks, being approximately 45-48 kilometres from attractions such as Walt Disney World Resort, Universal Studios Florida, and ICON Park.
The 167 square metre property boasts one bedroom, four bathrooms, sleeps fifteen guests, and includes a fully equipped kitchen, complimentary Wi-Fi, private parking, and a flat-screen TV.
3br/2ba Charming 1920's Lakefront Estate + Hot Tub - Leesburg, FL
9.5 153 reviews

3br/2ba Charming 1920's Lakefront Estate + Hot Tub

apartment, Yalaha
This three-bedroom cottage in Yalaha is situated on a lake, just 16 kilometres from the shops and restaurants of Mount Dora.
The 168 square metre property features a fully-equipped kitchen, a Jacuzzi, a garden and a spa, and can accommodate up to seven guests, making it ideal for families or groups of friends.
Sunset Cove - Leesburg, FL
9.0 2 reviews

Sunset Cove

house, Wildwood
This Wildwood villa, situated near Orlando Sanford International Airport (approximately 82km away), offers convenient access to the area's attractions, though its precise district within Wildwood requires further clarification.
The Sunset Cove property boasts 119 square metres of floor space, comprising one bedroom, two bathrooms, and accommodating up to seven guests, with free Wi-Fi, private parking, and a fully equipped kitchen.
Courtyard Villa W/ Lanai & Community Amenities! - Leesburg, FL
9.4 16 reviews

Courtyard Villa W/ Lanai & Community Amenities!

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.

Best Leesburg, FL holiday rentals with parking

Cute Little Canal Front Apartment-bring Your Boat! - Leesburg, FL
9.0 2 reviews

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.
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.
The Howey Mansion Grove Bungalow - Leesburg, FL
9.8 25 reviews

The Howey Mansion Grove Bungalow

bungalow, Yalaha
This detached house is located in old Florida, 2 blocks from Lake Harris and 4 kilometres from the historic Howey Mansion Estate.
Sleeping up to 7 guests across 3 bedrooms and 2 bathrooms, this property offers a full kitchen, laundry facilities, and a large screened front porch, set on over half an acre with Wi-Fi and air conditioning.
Brand New Designer Home - 5 Minutes From East Port - Leesburg, FL
9.5 2 reviews

Brand New Designer Home - 5 Minutes From East Port

house, Wildwood
This detached house in Adamsville is situated 34 kilometres from the Lake County Historical Museum and 39 kilometres from Eustis Square Shopping Centre, offering convenient access to local attractions.
This detached house provides accommodation for up to 13 guests across three bedrooms and two bathrooms, featuring a 167 square metre floor area, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, air conditioning, WiFi, on-site parking, and a garden with outdoor seating, with proximity to cycling routes and the Palisades Golf Club.

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?

    Silver Lake Guest Pool House, Cozy Corner ~ Close To The Villages And Disney and Canal Front Home On The Harris Lake Chain are the most popular Airbnb and vacation rentals in Leesburg, FL among travelers.

  • 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?

    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 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.

Popular destinations

Best Leesburg, FL holiday rentals with a balcony

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.
5 Minutes From Eastport Brand New Home - Leesburg, FL
No reviews

5 Minutes From Eastport Brand New Home

house, Wildwood
This brand new holiday home in Sumterville is located 82 kilometres from Orlando International Airport and within a 35-kilometre radius of the Lake County Historical Museum and Palisades Golf Club.
This spacious 139 square metre holiday house offers accommodation for 10 guests with two bedrooms, two bathrooms, a fully equipped kitchen including a fridge, microwave oven and dishwasher, air conditioning, a garden, parking, and an outdoor patio.
Coastal Cottage - Golf Cart & Near Sawgrass - Leesburg, FL
10 1 review

Coastal Cottage - Golf Cart & Near Sawgrass

house, Wildwood
This coastal cottage in Wildwood is located 80 kilometres from Orlando Sanford International Airport, with the Lake County Historical Museum 32 kilometres away and Palisades Golf Club 39 kilometres distant.
This holiday home offers 104 square metres of living space with two bedrooms and two bathrooms, accommodating up to seven guests, and features a heated swimming pool, garden, terrace, and free WiFi.

Best pet friendly Leesburg, FL holiday rentals

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

Where Every Day Feels Like A Florida Getaway! - Leesburg, FL
9.2 9 reviews

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.
Great 3/2 Villages Home With Amenities Access - Leesburg, FL
9.6 21 reviews

Great 3/2 Villages Home With Amenities Access

house, Leesburg
This brand-new three-bedroom patio villa is located in the Village of Lake Denham, The Villages, Florida, a short golf cart ride from Sawgrass Grove's shopping and entertainment, and a short drive from recreation centres and a golf course.
The 130 square metre (1,400 square foot) property features an open-plan layout, sleeps six guests comfortably, includes a fully equipped kitchen with stainless-steel appliances and a wine chiller, and offers a 4-passenger golf cart for exploring local amenities.
Cozy 2-bedroom Cottage - Leesburg, FL
9.8 13 reviews

Cozy 2-bedroom Cottage

cottage, The Villages
This 2-bedroom holiday home in The Villages offers convenient access to Lake Sumter Landing, a mere short golf cart journey away, featuring shops, restaurants, waterfront views, and nightly entertainment.
This property provides a comfortable base with air conditioning, Wi-Fi, a one-car garage, and a screened lanai, plus an included golf cart for exploring The Villages' golf courses, swimming pools, and recreation centres, and is situated within 5 kilometres of Uncle Donald's Farm and Leesburg Centre for the Arts.
Ev Friendly, Dog Friendly, Golf Cart 3/2 Courtyard Villa - Leesburg, FL
No reviews

Ev Friendly, Dog Friendly, Golf Cart 3/2 Courtyard Villa

house, Wildwood
This courtyard villa is situated in the Village of Hawkins, The Villages, Florida, a brief golf-cart journey from Sawgrass Grove and close to the Hawkins Neighbourhood Recreation Area and Ezell Recreation.
This 138 square meter residence accommodates up to six guests across three bedrooms and two bathrooms, featuring a screened lanai, an inside laundry room, a primary suite with a Roman-style walk-in shower, and a complimentary golf cart for exploring the area, with EV charging permitted.