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.

The Villages: Sumter Landing W/ Lanai & Patio! - Leesburg, FL
9.8 7 reviews
Leesburg, FL
25/06 – 29/06
£171/nighttotal: £684 (4 )

The Villages: Sumter Landing W/ Lanai & Patio!

3 2
apartment , The Villages
This three-bedroom, two-bathroom apartment in Sumter Landing, The Villages, enjoys a prime location near Spanish Springs Town Square and The Villages Market Square.
The 3-bedroom property sleeps eight guests, offering a kitchen with granite countertops and stainless steel appliances, a relaxing lanai, a screened porch, Wi-Fi, Roku TV, and parking; a 4-passenger golf cart rental is available from 1 October 2024.
The Lake Harris Bungalow - Leesburg, FL
10 33 reviews
Leesburg, FL
12/07 – 15/07
£162/nighttotal: £486 (3 )

The Lake Harris Bungalow

1 4
bungalow , Yalaha
This lakefront cottage in Yalaha, directly on Lake Harris, offers exceptional waterfront views and private access with EV/boat charging.
The property boasts two bedrooms (queen & twin XL), a full bathroom, full kitchen, WiFi, TV, screened porch with BBQ, and discounted pontoon boat rentals, accommodating up to four guests.
Palm Tree Pad | New 3br | Sawgrass | Golf Cart - Leesburg, FL
10 25 reviews
Leesburg, FL
12/07 – 19/07
£115/nighttotal: £805 (7 )

Palm Tree Pad | New 3br | Sawgrass | Golf Cart

1 4
apartment , Leesburg
This three-bedroom, two-bathroom villa is located in The Villages, Florida, a short distance from Southern Oaks and Jubilee golf courses and Brownwood Paddock Square.
The 3-bedroom property offers an open-plan layout, sleeping up to six guests, with a fully equipped kitchen, free Wi-Fi, Netflix, a private garden, swimming pool, parking for two cars and a garage for golf cart storage; an electric golf cart is included.
5 O`clock Somewhere - 3/2 W/ Golf Cart In The Village Of Lake Denham - Leesburg, FL
9.8 9 reviews
Leesburg, FL
25/06 – 29/06
£205/nighttotal: £820 (4 )

5 O`clock Somewhere - 3/2 W/ Golf Cart In The Village Of Lake Denham

3 2
apartment , Leesburg
This Leesburg holiday home, situated in Okahumpka, is conveniently located within 14.5 kilometres of Plantation Golf Club, Continental Country Club, and Lake Harlow Canine Park, offering easy access to local attractions.
This three-bedroom, two-bathroom property sleeps six guests and boasts a private pool, patio, fully equipped kitchen, free Wi-Fi, and on-site playground; nearby Lake Deaton and Venetian Gardens are also within 14.5 kilometres.

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.

Central Location!! Beautiful Villa With 2 Seater Gas Golf Cart & Wifi - Leesburg, FL
9.8 7 reviews
Leesburg, FL
25/06 – 29/06
£134/nighttotal: £536 (4 )

Central Location!! Beautiful Villa With 2 Seater Gas Golf Cart & Wifi

2 2
apartment , The Villages
This holiday flat is situated in The Villages' Hemingway district, a 7-minute drive from The Villages Market Square and 1.4 kilometres from Lake Griffin State Park.
This 110 square metre residence accommodates up to four guests across two bedrooms and two bathrooms, offering a fully equipped kitchen, air conditioning, free Wi-Fi, an in-unit washer and dryer, and a covered parking space.
Location! Walk To Lake Sumter Landing! 3/2 Villa W/ Gas Golf Cart, Bbq & Wifi - Leesburg, FL
9.2 9 reviews
Leesburg, FL
05/07 – 31/08
£70/nighttotal: £3990 (57 )

Location! Walk To Lake Sumter Landing! 3/2 Villa W/ Gas Golf Cart, Bbq & Wifi

3 1
apartment , The Villages
This three-bedroom villa is situated in the Creekside Landing neighbourhood of The Villages, Florida, within walking distance of Lake Sumter Landing Market Square and Edgewater Recreation Center, and a short drive from Canal Street Recreation Center.
The 130 square metre (1,400 square foot) property offers two bathrooms, sleeps six guests, and includes a fully equipped kitchen, screened lanai, gas golf cart, and access to local amenities such as swimming pools and numerous golf courses.
Luxury Tiny By Tiny Hamptons - Chefs Kitchen - Leesburg, FL
10 9 reviews
Leesburg, FL
01/01 – 31/03
£139/nighttotal: £12371 (89 )

Luxury Tiny By Tiny Hamptons - Chefs Kitchen

2 2
house , Groveland
This Groveland villa, situated 2.7km from Lakeridge Winery and within 9.6km of Cherry Lake and Palisades Golf Club, offers convenient access to local attractions.
The 33-square-metre property features two bedrooms, one bathroom, sleeps four guests, and boasts a private pool, hot tub, fitness centre, and barbecue grills, alongside a fully equipped kitchen.
Downtown Howey Home Next To Mission Inn - Leesburg, FL
9.5 92 reviews
Leesburg, FL
12/07 – 19/07
£114/nighttotal: £798 (7 )

Downtown Howey Home Next To Mission Inn

1 4
apartment , Howey-in-the-Hills
This three-bedroom property in Howey-in-the-Hills is conveniently located less than 1.6 kilometres from the Howey Mansion and Mission Inn, offering easy access to the area's attractions. The accommodation has received excellent ratings for its cleanliness, location, and overall experience.
The house is ideal for families, offering a spacious layout and accommodating up to six guests. Amenities include a fully equipped kitchen, a private garden, a game room with foosball, ping pong, and darts, and a comfortable living space with Netflix access.

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.

The Villages Lifestyle, Steps Away From Lake Sumter Square - Leesburg, FL
8.0 1 review
Leesburg, FL
01/08 – 30/09
£78/nighttotal: £4680 (60 )

The Villages Lifestyle, Steps Away From Lake Sumter Square

2 1
apartment , The Villages
This two-bedroom apartment is located in the Mallory Square neighbourhood of The Villages, a short 8km golf cart ride from Lake Sumter Square, the heart of the community. The property features a private garden, a swimming pool, and a spa, and can accommodate up to four guests.
Spacious 2br In The Villages! Near Eastport & Pool - Leesburg, FL
Leesburg, FL
25/06 – 29/06
£133/nighttotal: £532 (4 )

Spacious 2br In The Villages! Near Eastport & Pool

2 2
apartment , Wildwood
This two-bedroom flat is situated in Center Hill, Wildwood, offering convenient access to Eastport Town Square, approximately 7 minutes away, and Saluki Recreation, just 4 minutes distant.
This professionally managed accommodation for four guests features a king and two twin beds, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, high-speed Wi-Fi, Netflix, and a screened lanai patio, with access to The Villages' amenities via Lifestyle IDs.
Large 2 Bdrm & Den Designer Home W/golf Cart & Wifi! - Leesburg, FL
10 10 reviews
Leesburg, FL
05/07 – 31/08
£73/nighttotal: £4161 (57 )

Large 2 Bdrm & Den Designer Home W/golf Cart & Wifi!

2 1
apartment , The Villages
This two-bedroom apartment in The Villages' Gilchrist district is ideally situated within a short golf cart ride (around 2 km) of both Sumter Landing and Brownwood, offering easy access to the area's bustling town squares and amenities. It consistently receives excellent user ratings, indicating a high level of satisfaction from previous guests.
The 159 square metre apartment comfortably accommodates up to four guests and features a well-equipped kitchen, a dining area, and a relaxing living space. Guests can enjoy a range of amenities, including a swimming pool, fitness centre, tennis court, and a private lanai, as well as access to The Villages' extensive network of golf courses, recreational activities, and live entertainment options.
Waterfront Cottage On The Harris Chain In Leesburg - Leesburg, FL
9.8 224 reviews
Leesburg, FL
01/08 – 30/09
£93/nighttotal: £5580 (60 )

Waterfront Cottage On The Harris Chain In Leesburg

2 1
cottage , Lisbon
This charming cottage is situated just 3 kilometres from the Emeralda Marsh Conservation Area, Bell Hammock, and Big Hammock, offering easy access to nature trails and outdoor activities. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
The cottage is perfect for families, with space for up to 4 guests in its one bedroom and one bathroom. Guests can enjoy a range of amenities, including a fully equipped kitchen, a terrace, a jacuzzi, and a fireplace, offering a comfortable and relaxing stay.

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.

Charming & Beautifully Decorated Home W/bbq, Golf Cart, & A Bike - Leesburg, FL
9.2 16 reviews
Leesburg, FL
25/06 – 29/06
£162/nighttotal: £648 (4 )

Charming & Beautifully Decorated Home W/bbq, Golf Cart, & A Bike

3 2
apartment , Wildwood
This Wildwood property is conveniently located within a short drive of several attractions including lakes, golf courses, and a historical museum. It has received excellent user ratings, making it a popular choice for travellers.
The three-bedroom house spans 143 square metres, comfortably accommodating up to six guests. It features a fully equipped kitchen, laundry facilities, a barbecue grill, air conditioning, a fitness centre, a tennis court, and free Wi-Fi.
One Of A Kind Dog Villa Close To Lake Sumter Landing W/golf Cart, & Wifi! - Leesburg, FL
8.0 16 reviews
Leesburg, FL
01/08 – 30/09
£71/nighttotal: £4260 (60 )

One Of A Kind Dog Villa Close To Lake Sumter Landing W/golf Cart, & Wifi!

3 1
apartment , The Villages
This three-bedroom villa is located in Mallory Square, a peaceful setting just 3.7 kilometres from The Villages Market Square and 4.2 kilometres from Cane Garden Country Club. The property has consistently received very good user ratings.
The villa spans 150 square metres and comfortably accommodates up to six guests. It comes equipped with a fully fitted kitchen, two bathrooms, a washing machine, free Wi-Fi, and a range of other amenities, including a swimming pool, tennis court, and concierge services.
Welcome To Orange Blossom Cottage At Dirty Dog Organic Farm. - Leesburg, FL
10 2 reviews
Leesburg, FL
12/07 – 19/07
£119/nighttotal: £833 (7 )

Welcome To Orange Blossom Cottage At Dirty Dog Organic Farm.

2 4
farm , Leesburg
This Leesburg self-catering cottage offers a peaceful farm stay, conveniently located 4.8km from AMF Leesburg Lanes bowling alley, and within 9.6km of Lake Griffin State Park, Paquette's Historical Farmall Museum, and Venetian Gardens.
The two-bedroom, one-bathroom property sleeps four guests and includes a kitchen with fridge and microwave, air conditioning, a terrace, garden, parking, and Wi-Fi; change of towels is available on request.
Sunny Lakeside Retreat W/ Pool + Firepit - Leesburg, FL
9.3 9 reviews
Leesburg, FL
01/01 – 31/03
£167/nighttotal: £14863 (89 )

Sunny Lakeside Retreat W/ Pool + Firepit

1 2
apartment , Fruitland Park
This lakefront holiday home in Fruitland Park, Florida, is set on 3 acres, offering 800 meters from Lake Griffin State Park and 1.6 kilometers from The Villages.
This 3-bedroom, 2-bathroom flat accommodates up to 14 guests and features a private swimming pool, game room, and a fully equipped kitchen, with pets welcome.
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