Compare Vacation Rentals & Airbnb in Leesburg, FL

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

Best family friendly Leesburg, FL vacation rentals

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

New 2br The Villages | Golf Cart | Eastport Sq. - Leesburg, FL
Leesburg, FL
12/07 – 15/07
$229/nighttotal: $687 (3 )

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

2 4
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.
Welcome Small Dogs.. Elegant Villa, Golf Cart, Walk To Sumter Square, Sleep 6 - Leesburg, FL
9.6 131 reviews
Leesburg, FL
12/07 – 19/07
$174/nighttotal: $1218 (7 )

Welcome Small Dogs.. Elegant Villa, Golf Cart, Walk To Sumter Square, Sleep 6

2 4
house , The Villages
This two-bedroom villa in Virginia Trace is ideally located just a mile from The Villages Market Square and 2.4 miles from Cane Garden Country Club, offering easy access to shopping, dining, and entertainment. It has received excellent user ratings, making it a popular choice for travellers visiting The Villages.
The villa comfortably accommodates up to eight guests and features a well-equipped kitchen, a private garden, and a swimming pool. Enjoy a relaxing stay with amenities like air conditioning, free Wi-Fi, a terrace, and ample parking.
Fully Furnished Brand New Villa In Village Of St. Catherine's With Cart - Leesburg, FL
10 106 reviews
Leesburg, FL
01/08 – 30/09
$133/nighttotal: $7980 (60 )

Fully Furnished Brand New Villa In Village Of St. Catherine's With Cart

2 1
house , Wildwood
This two-bedroom property is situated in Wildwood, just 4km from Lake Deaton and Continental Country Club, offering easy access to outdoor activities and recreation. Guests have consistently rated this property as excellent, highlighting its comfortable and convenient features.
The villa comfortably accommodates up to six guests and features a well-equipped kitchen, a private patio, beach towels, free Wi-Fi, tennis court access, and a swimming pool. Enjoy the fresh air, relax by the pool, or take advantage of the nearby lake and country club for a day of outdoor fun.
Relax By Lake Eustis In Your Cozy 2-bedroom Retreat.10%discount For 7 Day Rental - Leesburg, FL
9.6 123 reviews
Leesburg, FL
25/06 – 29/06
$294/nighttotal: $1176 (4 )

Relax By Lake Eustis In Your Cozy 2-bedroom Retreat.10%discount For 7 Day Rental

2 2
apartment , Tavares
This lakeside home is situated in Lake County, just a short distance from Tavares and Mount Dora, offering a peaceful retreat with easy access to local attractions. The property has received excellent user ratings, highlighting its quality and appeal.
This two-bedroom apartment spans 125 square metres and comfortably accommodates up to five guests. The property offers a range of amenities, including a fully equipped kitchen, a private garden, a spa, and direct lakefront access with a fishing pier and boat storage.

Best Leesburg, FL vacation rentals with parking

Paradise On Lake Harris Apt #102 - Leesburg, FL
10 8 reviews
Leesburg, FL
01/08 – 30/09
$152/nighttotal: $9120 (60 )

Paradise On Lake Harris Apt #102

1 1
apartment , Leesburg
This apartment is located in Leesburg, just a short distance from Paquette's Historical Farmall Museum and Lake County Historical Museum, offering easy access to the town's cultural attractions. It has been consistently rated excellent by previous guests.
The self-catering apartment has one bedroom, one bathroom, and can accommodate up to four guests. You can enjoy lake views, fishing from the dock, or take a boat out on the water.
Perfect Location Between Brownwood & Lake Sumter - Leesburg, FL
9.8 112 reviews
Leesburg, FL
01/08 – 30/09
$145/nighttotal: $8700 (60 )

Perfect Location Between Brownwood & Lake Sumter

2 1
house , The Villages
This two-bedroom courtyard villa is situated in Tamarind Grove, just a 10-minute golf cart ride from both Lake Sumter Landing Square and Paddock Square, two of The Villages' vibrant town centres. The 117 square metre property features a fully equipped kitchen, a private screened lanai, a courtyard, and a 2016 Yamaha gas golf cart, ideal for exploring the many amenities of The Villages.
Cottage 35: Blue Heron Hideaway - Waterfront Lodging In Downtown Tavares, Fl - Leesburg, FL
Leesburg, FL
01/01 – 31/03
$167/nighttotal: $14863 (89 )

Cottage 35: Blue Heron Hideaway - Waterfront Lodging In Downtown Tavares, Fl

1 2
cottage , Tavares
This Tavares waterfront cottage is situated a short walk from Dora Canal, offering easy access to boating, fishing, and the Lake County Historical Museum, approximately 45 minutes north of Orlando.
The 31-square-metre (334 square feet) self-catering property features one bedroom, one bathroom, sleeps two guests, and includes air conditioning, a kitchen with fridge and microwave, plus on-site parking and access to a spa.
Free Golf Cart! Fabulous Location! Classy Decor! Pet-friendly! - Leesburg, FL
10 60 reviews
Leesburg, FL
25/06 – 29/06
$242/nighttotal: $968 (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.

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.

Destinations nearby

Best Leesburg, FL vacation rentals with a balcony

Charming Home In The Villages - Golf Cart & Bbq - Near Brownwood Paddock Park - Leesburg, FL
9.6 25 reviews
Leesburg, FL
01/08 – 30/09
$91/nighttotal: $5460 (60 )

Charming Home In The Villages - Golf Cart & Bbq - Near Brownwood Paddock Park

2 1
apartment , The Villages
This smoke-free holiday home is located in Fernandina, just 1.6 kilometres from Lake Deaton and within a 10-kilometre radius of several popular attractions including Cane Garden Country Club, Lake Okahumpka Park, Continental Country Club, and The Villages Market Square. This property has received excellent reviews from previous guests.
The property spans 107 square metres and comfortably accommodates up to four guests in its two bedrooms and two bathrooms. The home offers a range of amenities, including a fully equipped kitchen, a washing machine, free Wi-Fi, air conditioning, a swimming pool, a barbecue grill, and parking.
Beautifully Decorated 3 Bdrm Home W/open Floor Plan, Bbq & Wifi - Leesburg, FL
9.6 4 reviews
Leesburg, FL
05/07 – 31/08
$136/nighttotal: $7752 (57 )

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

3 1
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.
Walk To Saluki Recreational Center, Minnutes To Eastport With Golfcart - Leesburg, FL
Leesburg, FL
01/01 – 31/03
$518/nighttotal: $46102 (89 )

Walk To Saluki Recreational Center, Minnutes To Eastport With Golfcart

2 2
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.
Spacious Golf Retreat-2 King Beds-golf Cart- Full Kitchen & Tvs In Every Room - Leesburg, FL
Leesburg, FL
01/01 – 31/03
$529/nighttotal: $47081 (89 )

Spacious Golf Retreat-2 King Beds-golf Cart- Full Kitchen & Tvs In Every Room

3 2
house , Wildwood
This spacious three-bedroom holiday home, The Golfer's Edge, is located in Sumterville, Florida, approximately 35-43 kilometres from several golf courses including the Palisades Golf Club, Presidents Hall of Fame, and Deer Island Golf Lake Club, and around 80 kilometres from Orlando International Airport.
The 1680 square metre property boasts a fully equipped kitchen, two bathrooms with walk-in showers and bidets, a terrace, private parking, a swimming pool, and accommodates up to ten guests, offering Wi-Fi and a private entrance with full-day security.

Best pet friendly Leesburg, FL vacation rentals

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

Beautifully Decorated Sm Dog Friendly Villa W/bbq, Bicycles & Wifi! - Leesburg, FL
9.6 5 reviews
Leesburg, FL
01/08 – 30/09
$138/nighttotal: $8280 (60 )

Beautifully Decorated Sm Dog Friendly Villa W/bbq, Bicycles & Wifi!

2 1
apartment , The Villages
This Duval property, a two-bedroom house in The Villages, Florida, is situated 3.4km from Cane Garden Country Club and within 9.7km of both The Villages Market Square and Lake Deaton.
This 150 square metre holiday home offers a fully equipped kitchen, private garden, swimming pool, tennis court, and parking, accommodating up to four guests and including free Wi-Fi.
The Mclucas Getaway (Lake Denham) - Leesburg, FL
8.5 4 reviews
Leesburg, FL
05/07 – 31/08
$162/nighttotal: $9234 (57 )

The Mclucas Getaway (Lake Denham)

3 1
apartment , Leesburg
This three-bedroom, two-bathroom apartment is situated in the Village of Lake Denham within The Villages, Florida, approximately 1.6km from Franklin and Homestead Recreation Centres, and within 1.6km of Sawgrass Grove and Ezell Recreation Complex.
The 3-bedroom property offers a spacious open-plan living area, sleeping up to six guests, and features a fully equipped kitchen, a screened lanai, and proximity to numerous recreational facilities including swimming pools and pickleball courts.
Waterfront Cottage On Haynes Creek - Leesburg, FL
9.4 13 reviews
Leesburg, FL
25/06 – 29/06
$184/nighttotal: $736 (4 )

Waterfront Cottage On Haynes Creek

1 2
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.
Tiny Hamptons, No Pet Fees, Main Floor Bed - Leesburg, FL
10 18 reviews
Leesburg, FL
12/07 – 15/07
$270/nighttotal: $810 (3 )

Tiny Hamptons, No Pet Fees, Main Floor Bed

3 4
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.
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