Holiday Rentals in Leesburg, FL

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

Paradise On Lake Harris Apt #102 - Leesburg, FL
9.9 27 reviews
Leesburg, FL
27/06 – 04/07
SG$254/nighttotal: SG$1778 (7 )

Paradise On Lake Harris Apt #102

1 2
apartment , Leesburg
This lakeside flat is located in Leesburg, just a short walk from Venetian Gardens and a 50-kilometre drive from Disney World. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The self-catering property is ideal for families or groups of up to four people, featuring a bedroom, a bathroom, and a well-equipped kitchen. Guests can enjoy the private backyard oasis, the fully furnished living space, and the convenience of on-site laundry facilities.
Best Of The Villages!  2br/2ba Home & Amenity Acce - Leesburg, FL
9.6 22 reviews
Leesburg, FL
27/06 – 04/07
SG$229/nighttotal: SG$1603 (7 )

Best Of The Villages! 2br/2ba Home & Amenity Acce

2 2
apartment , Leesburg
This two-bedroom, two-bathroom patio villa is located in the Village of Lake Denham within The Villages, Florida, a short golf cart ride (approximately 1.6km) from Sawgrass Grove shopping and dining.
The 4-guest property boasts a spacious open-plan layout, a fully equipped kitchen with stainless steel appliances, and family-friendly amenities including a highchair and Pack 'n' Play, plus access to nearby recreation centres with pools and sports facilities.
Tranquil Central Fl Retreat - Leesburg, FL
9.8 14 reviews
Leesburg, FL
25/06 – 29/06
SG$270/nighttotal: SG$1080 (4 )

Tranquil Central Fl Retreat

3 2
apartment , Leesburg
This Leesburg holiday home is situated near Fern Prairie Preserve and within 5km of Lake Sumter Landing, offering easy access to Lake Square Mall, ViaPort Florida, and the Paul P. Williams Auditorium.
The 121 square metre property boasts three bedrooms, two bathrooms, sleeps nine guests, and includes a sauna, spa, private garden, barbecue facilities, and free Wi-Fi.
Fully Furnished Brand New Villa In Village Of St. Catherine's With Cart - Leesburg, FL
10 108 reviews
Leesburg, FL
27/06 – 04/07
SG$108/nighttotal: SG$756 (7 )

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

2 2
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.

Best Leesburg, FL holiday rentals with parking

Cottage 33: Pineapple Place - Waterfront Lodging In Downtown Tavares, Fl - Leesburg, FL
Leesburg, FL
01/01 – 31/03
SG$146/nighttotal: SG$12994 (89 )

Cottage 33: Pineapple Place - Waterfront Lodging In Downtown Tavares, Fl

1 2
cottage , Tavares
This Tavares waterfront cottage, situated steps from Dora Canal and within walking distance of Tavares' town centre, offers easy access to Lake County Historical Museum and Paul P. Williams Auditorium.
The 22-square-metre (approximately 237-square-foot) self-catering property features one bedroom, one bathroom, and sleeps two, boasting a private spa, air conditioning, assigned parking, and access to a community fish cleaning station and laundromat.
Beautiful 2/2 Dog Friendly Patio Villa W/bbq & Close To Lake Sumter Landing! - Leesburg, FL
9.2 9 reviews
Leesburg, FL
27/06 – 04/07
SG$177/nighttotal: SG$1239 (7 )

Beautiful 2/2 Dog Friendly Patio Villa W/bbq & Close To Lake Sumter Landing!

2 2
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.
Blissful Village Bungalow 2br-2ba & Membership Ame - Leesburg, FL
9.2 23 reviews
Leesburg, FL
27/06 – 04/07
SG$184/nighttotal: SG$1288 (7 )

Blissful Village Bungalow 2br-2ba & Membership Ame

1 2
apartment , Leesburg
This brand-new two-bedroom patio villa is located in the Village of Lake Denham within The Villages, Florida, a short golf cart ride from Sawgrass Grove's shopping and entertainment and several recreation centres.
The 2-bedroom, 2-bathroom property offers an open-plan layout, sleeps four guests, and includes a fully equipped kitchen, 75" smart Roku TV, in-unit laundry, outdoor lanai with gas grill, highchair and Pack 'n' Play, plus a golf cart for easy access to local amenities.
Charming Rental In The Village Of Pinellas: Your Florida Oasis Awaits - Leesburg, FL
9.8 10 reviews
Leesburg, FL
01/08 – 30/09
SG$89/nighttotal: SG$5340 (60 )

Charming Rental In The Village Of Pinellas: Your Florida Oasis Awaits

2 1
apartment , The Villages
This two-bedroom villa is located in Wildwood, just 4.2 kilometres from Lake Deaton and within a 10 kilometre radius of several attractions including Lake Okahumpka Park and Cane Garden Country Club. The property has received excellent user ratings and is perfect for a relaxing getaway.
The 108 square metre villa comfortably accommodates up to four guests. Enjoy a private setting with a swimming pool, tennis court, and garden, as well as a fully equipped kitchen and free Wi-Fi.

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.

Destinations nearby

Best Leesburg, FL holiday rentals with a balcony

Holiday Vacation Rental Home - Leesburg, FL
Leesburg, FL
27/06 – 04/07
SG$441/nighttotal: SG$3087 (7 )

Holiday Vacation Rental Home

3 2
apartment , Leesburg
This 3-bedroom holiday flat in Leesburg is located in a secluded area of Holiday RV Village, offering convenient access to ViaPort Florida (approximately 3.5 kilometres away) and Lake Square Mall, as well as proximity to Lake Griffin State Park and Fern Prairie Preserve.
This accommodation provides space for up to 8 guests with 3 bedrooms and 3 bathrooms, featuring a private outdoor entertaining area with a pool and spa, alongside access to resort amenities including a marina, fitness centre, and sports courts, with an optional suite available for extra capacity.
Charming Large 3-bedroom 2 Bath House In The Villages. - Leesburg, FL
Leesburg, FL
27/06 – 04/07
SG$242/nighttotal: SG$1694 (7 )

Charming Large 3-bedroom 2 Bath House In The Villages.

3 2
apartment , The Villages
This 2,200 sq ft flat is located in the Bridgeport district at Lake Miona, offering direct access across the street to Palmer Legends Golf & Country Club and is just minutes from Lake Sumter Landing.
This property provides accommodation for six guests across three bedrooms and two bathrooms, featuring a microwave oven, dishwasher, air conditioning, and a terrace, with guest passes for golf included and a golf cart rental option available.
Close To Pelican Heron Golf Course And Only  7 Minutes To Lake Sumter Landing - Leesburg, FL
Leesburg, FL
27/06 – 27/07
SG$189/nighttotal: SG$5670 (30 )

Close To Pelican Heron Golf Course And Only 7 Minutes To Lake Sumter Landing

3 2
apartment , The Villages
This three-bedroom apartment is situated in Sunset Pointe, a short distance from the Sunset Pointe Pool & Lake Miona Recreation Centre and just 4.5 kilometres from the central hub of The Villages, Lake Sumter Landing.
The 138 square metre property is fully furnished and can accommodate up to six guests, with amenities including a private garden, swimming pool, and a screened-in lanai.
Villages2530-gorgeous Florida Rental !! - Leesburg, FL
9.8 8 reviews
Leesburg, FL
25/06 – 29/06
SG$718/nighttotal: SG$2872 (4 )

Villages2530-gorgeous Florida Rental !!

3 2
apartment , The Villages
This three-bedroom apartment is located in Hadley, just under 8 kilometres from Lake Deaton and within 10 kilometres of The Villages Market Square, Cane Garden Country Club, Continental Country Club, and Spanish Springs Town Square, offering a peaceful retreat away from the hustle and bustle of the town centres.
The property comfortably sleeps eight guests and features a fully equipped kitchen, a private balcony, a swimming pool, and a garden. Guests can enjoy a range of activities including golf, swimming, and exploring the local area.

Best pet friendly Leesburg, FL holiday rentals

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

Village Of Charlotte Retreat: 3br, 2ba Home, Golf Cart, & Dog-friendly Bliss - Leesburg, FL
9.6 13 reviews
Leesburg, FL
27/06 – 04/07
SG$228/nighttotal: SG$1596 (7 )

Village Of Charlotte Retreat: 3br, 2ba Home, Golf Cart, & Dog-friendly Bliss

3 2
apartment , The Villages
This holiday let is situated in the Village of Charlotte within The Villages, offering convenient access to Brownwood Paddock Park, approximately 1.5 kilometres away, for shopping, dining, and entertainment.
This spacious 138 square metre apartment accommodates up to six guests across three bedrooms, featuring a master suite with a king-sized bed and en-suite, two guest rooms with queen beds (one a sofa bed), two bathrooms, a well-equipped kitchen, air conditioning, a swimming pool, a screened lanai with a gas BBQ, and a golf cart for exploring the amenities.
Royal Oak Lakeview Serenity - Leesburg, FL
9.9 49 reviews
Leesburg, FL
12/07 – 15/07
SG$363/nighttotal: SG$1089 (3 )

Royal Oak Lakeview Serenity

1 4
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.
Walk To Lake Sumter Landing! Our Village Gem - 10 Star - W/ Golf Cart - Leesburg, FL
10 123 reviews
Leesburg, FL
12/07 – 15/07
SG$201/nighttotal: SG$603 (3 )

Walk To Lake Sumter Landing! Our Village Gem - 10 Star - W/ Golf Cart

2 4
apartment , The Villages
This two-bedroom house is located in Caroline, just 1.3 kilometres from The Villages Market Square and 4.2 kilometres from Cane Garden Country Club, offering a peaceful retreat from the hustle and bustle of the central areas. It has received excellent user ratings, making it a popular choice for travellers.
The house spans 119 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, a patio for outdoor enjoyment, a washing machine, and a garden with barbecue facilities, providing everything you need for a relaxing and enjoyable stay.
Near Sawgrass Grove In The Village Of Newell - Leesburg, FL
9.5 4 reviews
Leesburg, FL
12/07 – 19/07
SG$199/nighttotal: SG$1393 (7 )

Near Sawgrass Grove In The Village Of Newell

3 4
apartment , Leesburg
This pet-friendly flat in The Village of Newell offers a peaceful retreat with pastoral views, located a short distance from Leesburg's attractions.
Accommodating up to six guests, this residence features three bedrooms, two bathrooms, a den with a sleeper sofa, and a garden, with a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
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