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 Holiday Rentals for Families in Leesburg, FL

Discover kid-friendly holiday rentals in Leesburg, FL with city attractions within easy reach. Holidays are better when everyone is comfortable.

Luxury Living In The Villages - Leesburg, FL
10 8 reviews
Leesburg, FL
27/06 – 27/07
£109/nighttotal: Â£3270 (30 )

Luxury Living In The Villages

1 2
apartment , Leesburg
This three-bedroom house is situated in The Villages, Florida, offering convenient access to Sawgrass Market and numerous recreation centres and pools.
The property boasts a bright, open-plan layout, sleeps four guests, includes a fully equipped kitchen, three ensuite bathrooms, a private garden, and a complimentary golf cart for exploring The Villages, with a picturesque pitch & putt golf course directly outside.
Sunset Cove - Leesburg, FL
9.0 2 reviews
Leesburg, FL
01/08 – 30/09
£92/nighttotal: Â£5520 (60 )

Sunset Cove

2 1
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.
Amazing Three-bedroom Home In The Villages. Great Spot For A Memorable Vacation! - Leesburg, FL
10 10 reviews
Leesburg, FL
25/06 – 29/06
£164/nighttotal: Â£656 (4 )

Amazing Three-bedroom Home In The Villages. Great Spot For A Memorable Vacation!

3 2
apartment , Fruitland Park
This property is situated in Fruitland Park, just 9.6km from the Country Club of Lady Lake, Lake Griffin, and Lake Griffin State Park, offering easy access to outdoor activities and recreation. It has received excellent user ratings.
The house has 3 bedrooms and 2 bathrooms, accommodating up to 8 guests. It offers a range of amenities including a swimming pool, jacuzzi, tennis court, and a garden with barbecue grills, perfect for relaxing and enjoying the Florida sunshine.
Howey In The Hills Home Next To Howey Mansion - Leesburg, FL
9.5 94 reviews
Leesburg, FL
12/07 – 15/07
£129/nighttotal: Â£387 (3 )

Howey In The Hills Home Next To Howey Mansion

1 4
apartment , Howey-in-the-Hills
This comfortable apartment is situated just under 1.6 kilometres from the Howey Mansion, Mission Inn, and Little Lake Harris, placing you within easy reach of the town's main attractions. The apartment enjoys a peaceful location, yet remains close to shops, restaurants, and the lake. It has received excellent ratings for its cleanliness, location, and overall experience.
This three-bedroom apartment can comfortably accommodate up to six guests. It has a fully equipped kitchen with a fridge, freezer, and microwave, plus air conditioning, a garden, and parking. You can also enjoy the benefits of free internet access and the option to bring your pet along.

Top Holiday Rentals with Parking in Leesburg, FL

Free on-site parking comes with these holiday rentals in Leesburg, FL, allowing you to focus on the city centre from day one.

Fly-in Place To Stay Close To The Villages - Leesburg, FL
9.7 40 reviews
Leesburg, FL
01/01 – 31/03
£122/nighttotal: Â£10858 (89 )

Fly-in Place To Stay Close To The Villages

1 2
cottage , Fruitland Park
This charming cottage is situated on a secluded 5-acre plot near Fruitland Park, offering peace and quiet while being just a short drive from the Villages and its shops and entertainment. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage comfortably accommodates two guests and provides access to a private pool, laundry facilities, and a spacious garden. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, and a private runway for those arriving by air.
Best Of The Villages!  2br/2ba Home & Amenity Acce - Leesburg, FL
9.6 22 reviews
Leesburg, FL
12/07 – 19/07
£120/nighttotal: Â£840 (7 )

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

2 4
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.
Paradise On Lake Harris Apt #102 - Leesburg, FL
Leesburg, FL
12/07 – 15/07
£178/nighttotal: Â£534 (3 )

Paradise On Lake Harris Apt #102

1 4
apartment , Leesburg
Paradise on Lake Harris Apt #102 is located in Leesburg, just 16km from Mount Dora and 24km from Eustis, offering easy access to historical museums, parks, and shopping centres. This apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment has one bedroom, one bathroom, and a floor area of 57 square metres, comfortably accommodating up to four guests. It features a fully equipped kitchen, air conditioning, private parking, a garden, and a washing machine, as well as stunning lake views and access to water activities.
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees - Leesburg, FL
10 19 reviews
Leesburg, FL
27/06 – 04/07
£116/nighttotal: Â£812 (7 )

Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees

3 2
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.

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 is during the shoulder seasons, from March to May and September to November, as you'll find better deals and less crowds.
  • What are the best Airbnb and holiday rentals in Leesburg, FL?

  • What events or festivals should visitors check out in and around Leesburg, FL?

    The Leesburg Bike Fest is a popular event in April, with live music and motorcycle displays. In October, the Leesburg International Festival brings in food, music and crafts from around the world.
  • 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?

    A walk around the Leesburg Waterfront Park is free and offers great views of Lake Harris. You can also enjoy a picnic at Venetian Gardens, or browse the shops and restaurants on Main Street.
  • What are the best holiday rentals with a pool in Leesburg, FL?

  • What are the best restaurants with local dishes in Leesburg, FL?

    The Brownwood Hotel has a great restaurant serving local dishes, and the Gator Dock Restaurant is a good option for seafood. For a more casual setting, try the Leesburg Farmers Market for local produce and snacks.
  • 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 walking path is a popular choice, and the Leesburg Trail offers a longer, scenic route. For cycling, the Lake County Loop is a great option with beautiful views of the lakes.
  • What are the best rentals or Airbnbs with a jacuzzi in Leesburg, FL?

  • Are there pet-friendly attractions in Leesburg, FL?

    Yes, many parks and trails in Leesburg are pet-friendly, including Venetian Gardens and the Leesburg Waterfront Park. The Leesburg Animal Park also has a dog park area.
  • What are the benefits of choosing a vacation rental in Leesburg, FL?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like a kitchen and laundry facilities. They can also be a more budget-friendly option, especially for families or groups.
  • What are the top sports attractions and facilities in Leesburg, FL?

    Leesburg has a number of sports facilities, including the Leesburg Recreation Complex, which has baseball fields, tennis courts, and a swimming pool. The Leesburg Golf Course is a popular option for golfers.

Destinations nearby

Check Out Holiday Rentals with a Balcony in Leesburg, FL

Enjoying morning coffee with city skyline views is a simple pleasure when staying in these holiday rentals and Airbnbs in Leesburg, FL.

Spacious 4-bedroom Country House In Peaceful Fruitland Park With Ac - Leesburg, FL
Leesburg, FL
01/01 – 31/03
£272/nighttotal: Â£24208 (89 )

Spacious 4-bedroom Country House In Peaceful Fruitland Park With Ac

4 2
manor house , Fruitland Park
This farm stay in Fruitland Park is situated near Lake Griffin State Park and Fern Prairie Preserve, with Leesburg Centre for the Arts and Uncle Donald's Farm also in close proximity.
This country house offers accommodation for up to 11 guests across four bedrooms and three bathrooms, featuring air conditioning, a kitchen with a fridge and microwave, and a garden with parking.
Experience The Villages Lifestyle In This Beautiful  Patio Villa! - Leesburg, FL
Leesburg, FL
12/07 – 19/07
£107/nighttotal: Â£749 (7 )

Experience The Villages Lifestyle In This Beautiful Patio Villa!

2 4
house , The Villages
This patio villa in the Village of St. John's offers an authentic Villages experience, situated 1.2 kilometres from Brownwood Square and Sawgrass Grove, and a short drive from the Southern Oaks Championship Course.
This accommodation for four includes two bedrooms, two bathrooms, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, and parking, with nearby access to Lake Griffin State Park and Uncle Donald's Farm for outdoor pursuits.
Close To Pelican Heron Golf Course And Only  7 Minutes To Lake Sumter Landing - Leesburg, FL
Leesburg, FL
27/06 – 27/07
£110/nighttotal: Â£3300 (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.
New 2br The Villages | Golf Cart | Eastport Sq. - Leesburg, FL
Leesburg, FL
27/06 – 04/07
£123/nighttotal: Â£861 (7 )

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

2 2
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.

Find the Best Dog-Friendly Self-Catering Rentals in Leesburg, FL

Travelling with a pet to Leesburg, FL is easy when your holiday rental is properly set up with nearby dog parks and city walks.

Comfortably Decorated 3/2 Sm Dog-friendly Home W/golf Cart & Wifi Included! - Leesburg, FL
10 25 reviews
Leesburg, FL
27/06 – 27/07
£77/nighttotal: Â£2310 (30 )

Comfortably Decorated 3/2 Sm Dog-friendly Home W/golf Cart & Wifi Included!

3 2
apartment , The Villages
This holiday home is situated in Wildwood, just over 3 kilometres from Lake Deaton and Continental Country Club, and within 10 kilometres of Lake Okahumpka Park and Paquette's Historical Farmall Museum. The property has received excellent user ratings, making it a popular choice for travellers.
The 184 square metre house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The property features a fully equipped kitchen, air conditioning, a swimming pool, a tennis court, and a barbecue area, making it ideal for families and groups seeking a relaxing and enjoyable stay.
Great 3/2 Villages Home With Amenities Access - Leesburg, FL
9.6 21 reviews
Leesburg, FL
01/08 – 30/09
£95/nighttotal: Â£5700 (60 )

Great 3/2 Villages Home With Amenities Access

3 1
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.
Ranch Retreat: Luxury Living In Village Charm! - Leesburg, FL
8.0 1 review
Leesburg, FL
01/01 – 31/03
£202/nighttotal: Â£17978 (89 )

Ranch Retreat: Luxury Living In Village Charm!

3 2
apartment , The Villages
This three-bedroom property is situated in the Village of Charlotte, Wildwood, conveniently located between Lake Sumter and Brownwood Town Squares, approximately 8km from both.
The 124 square metre ranch-style dwelling boasts an open-plan layout, sleeping up to six guests, and includes a well-equipped kitchen, private pool, and internet access; nearby amenities include the Bonifay Executive Golf Course and Charlotte Adult Pool.
Fantastic Apartment With Ac In Charming Downtown Leesburg - Leesburg, FL
9.8 7 reviews
Leesburg, FL
27/06 – 04/07
£98/nighttotal: Â£686 (7 )

Fantastic Apartment With Ac In Charming Downtown Leesburg

1 2
apartment , Leesburg
This one-bedroom flat in Leesburg is situated a mere 50 metres from the downtown area, within blocks of Lake Griffin and Lake Harris, and is within walking distance of the Leesburg Centre for the Arts and Paquette's Historical Farmall Museum.
This accommodation for up to three guests offers a private sitting area with a barbecue, air conditioning, Wi-Fi, and is conveniently located near ViaPort Florida and Lake Square Mall, with a check-out time of 11:00 AM.
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