Compare Vacation Rentals & Airbnb in Leesburg, FL

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Leesburg, FL vacation rentals
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297 Rentals and Airbnb in Leesburg, FL

Best family friendly Leesburg, FL vacation rentals

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

Get Cozy In This Renovated Home By The Villages - Leesburg, FL
10 1 review

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.
Spacious 3br · Sleeps 7 · King Bed · Lanai - Leesburg, FL
No reviews

Spacious 3br · Sleeps 7 · King Bed · Lanai

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.
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.
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.

Best Leesburg, FL vacation rentals with parking

Royal Oak Lakeview Serenity - Leesburg, FL
9.9 54 reviews

Royal Oak Lakeview Serenity

apartment, Leesburg
This Leesburg lakeside bungalow, boasting stunning Lake Harris views and private beach access (no dock), is conveniently located near three restaurants within walking distance, with Publix supermarket and further dining options a short 3.2km drive away, and major attractions and The Villages within a 16-32km radius.
This renovated 2100 sq ft (195 sq m) three-bedroom, two-bathroom house sleeps eight, features a game room with darts, pool, and ping pong, an outdoor kitchen with pergola, and a covered RV carport (power hookup extra); boat launch ramps are nearby.
Cozy Home W/ Game Room Villages And Lake Harris - Leesburg, FL
8.8 15 reviews

Cozy Home W/ Game Room Villages And Lake Harris

apartment, Leesburg
This Leesburg holiday home is situated within 5km of AMF Leesburg Lanes bowling alley, Venetian Gardens, and UF Health Leesburg Hospital, and 3.9km from Lake Griffin.
The two-bedroom property sleeps four guests and boasts a fully equipped kitchen, private patio, free Wi-Fi, and access to on-site amenities including a games room and barbecue grills.
Magnolia & Moon Cottage In Downtown - Leesburg, FL
No reviews

Magnolia & Moon Cottage In Downtown

apartment, Leesburg
This restored 1925 bungalow is located in a peaceful Old Florida district of Leesburg, offering a tranquil setting under mature trees, within easy reach of local attractions.
This 3-bedroom, 2-bathroom property accommodates up to 8 guests and features air conditioning, a kitchen, and internet, providing a comfortable base for exploring the area's historical character and slower pace of life.
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.

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

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.
Cozy Family Stay- Queen-double-twins Bed- Full Kitchen-netflix-golf Cart-wifi - Leesburg, FL
9.6 6 reviews

Cozy Family Stay- Queen-double-twins Bed- Full Kitchen-netflix-golf Cart-wifi

house, Okahumpka
The Pin High Pad is situated in Okahumpka, Florida, conveniently located approximately 24km from the Lake County Historical Museum and 29km from the Palisades Golf Club.
This three-bedroom, two-bathroom holiday home boasts 156 square metres of floor space, sleeping up to 11 guests and offering a swimming pool, terrace, free Wi-Fi, and private parking; nearby attractions include Deer Island Golf Lake Club.
Cozy Rental In The Villages, Pet-friendly, Close To Shopping! - Leesburg, FL
9.0 7 reviews

Cozy Rental In The Villages, Pet-friendly, Close To Shopping!

apartment, The Villages
This pet-friendly apartment in the Village of Duval, The Villages, Florida, is conveniently located near Lake Sumter Landing Town Square and Brownwood Paddock Square.
The 94 square metre self-catering property boasts a split-floorplan, sleeping up to four guests, and includes two bedrooms, two bathrooms, a well-equipped kitchen, and a private enclosed lanai; nearby amenities include swimming pool and parking.
4-pass Golf Cart  Corner Villa  Near Sawgrass Grove  Office  Large Garden - Leesburg, FL
No reviews

4-pass Golf Cart Corner Villa Near Sawgrass Grove Office Large Garden

apartment, Leesburg
This Leesburg flat, situated in ÃŽle Bouvet, is conveniently located near Eastport and Sawgrass, offering a dedicated office and a 4-person golf cart for local exploration.
This three-bedroom, two-bathroom residence provides complimentary Wi-Fi, air conditioning, a kitchen, laundry facilities, a garden, on-site swimming pool, and parking, with towels and an ironing board provided for guest convenience.

Best pet friendly Leesburg, FL vacation rentals

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

Joseph`s Oasis At Dabney Near Sawgrass, Eastport And Nature Trails - Leesburg, FL
No reviews

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.
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+ Shuffleboard Table + Wildlife Spotting - Leesburg, FL
9.3 20 reviews

Lakeview+ Shuffleboard Table + Wildlife Spotting

apartment, Fruitland Park
This Fruitland Park flat offers lake views and is conveniently located 10 minutes from The Villages and 7 minutes from Lake Griffin State Park.
This pet-friendly residence accommodates up to 10 guests with three bedrooms, two bathrooms, and features direct lake access for fishing and scenic enjoyment, alongside a fully stocked kitchen and central air conditioning.
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.
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