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Top Holiday Rentals in Leesburg

Spacious 4 bedroom 3.5 bath POOL home W/ Gym!!

8.8 out of 10, Excellent, (3)
"I highly recommend this property. The house was located in a very nice community easily accessible from any part of Leesburg. We had an amazing stay and will definitely be going back again."
The price is £474
includes taxes & fees
8 Jul - 9 Jul
Spacious 4 bedroom 3.5 bath POOL home W/ Gym!!

Guest House with pool, boat parking

8.6 out of 10, Excellent, (20)
"Richard was great with communicating and his home was welcoming, quiet and secure. Clean property with tons of local amenities. Would definitely stay again. "
The price is £136
includes taxes & fees
6 Jul - 7 Jul
Guest House with pool, boat parking

Boat Friendly & Private Pool Near The Villages

9.8 out of 10, Exceptional, (18)
"Had a great time and place was nice."
Boat Friendly & Private Pool Near The Villages

Siena at Bella Collina

3.5 star property
9.8 out of 10, Exceptional, (67)
"It’s nice and beautiful place."
Siena at Bella Collina

2 King 2 Twin 1 Queen Enormous Deck 3 BD Lakeview House at Waterfront Park

10.0 out of 10, Exceptional, (8)
"We loved staying at this beautiful home! It is so well decorated. Seems like they thought of just about everything! We definitely plan to stay here again."
The price is £269
includes taxes & fees
7 Jul - 8 Jul
2 King 2 Twin 1 Queen Enormous Deck 3 BD Lakeview House at Waterfront Park

Better Than A 5 Star Hotel IN THE VILLAGES 2 Bedroom house WiFi, AC, GOLF CART

2.0 star property
9.8 out of 10, Exceptional, (20)
"Very well managed"
The price is £179
includes taxes & fees
13 Jul - 14 Jul
Better Than A 5 Star Hotel IN THE VILLAGES 2 Bedroom house WiFi, AC, GOLF CART

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very good, (30)
"Great location!"
Historic Tremain Cottages

Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

10.0 out of 10, Exceptional, (209)
"We loved our stay! The house is spacious, well stocked, clean and great location. We enjoyed relaxing on the lanai with the beautiful view of the golf course and pool. David is an excellent host! "
Golf Front Home, Solar Heat Pool! FREE golf cart, wifi, awesome view

The Villages FL Golfing Community. Close to restaurants, beaches and shopping.

9.8 out of 10, Exceptional, (19)
"We only visited overnight but enjoyed our stay. Beds are super comfortable and house met our needs. Lora was great to work with and made our trip seamless start to finish. "
The price is £311
includes taxes & fees
8 Jul - 9 Jul
The Villages FL Golfing Community. Close to restaurants, beaches and shopping.

Charming 2-bedroom apartment in house with AC, WiFi included

The price is £117
includes taxes & fees
23 Jul - 24 Jul
Charming 2-bedroom apartment in house with AC, WiFi included

Village of Mallory, Close to Sumter Landing Sq. 3BD, 2Bath with Gas Golf Cart.

9.2 out of 10, Wonderful, (47)
"Centrally located to where we needed to be. Owner very quick to respond to our needs"
Village of Mallory, Close to Sumter Landing Sq. 3BD, 2Bath with Gas Golf Cart.

Private Pool, Golf Cart, & Pet Friendly. Close to Golf and Town Squares.

10.0 out of 10, Exceptional, (2)
"Great place in a very convenient location "
Private Pool, Golf Cart, & Pet Friendly. Close to Golf and Town Squares.

WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+

9.6 out of 10, Exceptional, (105)
"We had a great stay in the Villages. The villa was perfect for us. Close to Sumter Landing. Dogs enjoyed the back yard. We look forward to coming back!"
WOW.. ELEGANT Courtyard Villa, GOLF CART, Walk to Sumter Square & pool, sleep 6+

"Mermaid House" in Downtown Mt. Dora!! Pet Friendly

10.0 out of 10, Exceptional, (57)
"This how was perfect for our weekend anniversary trip. It’s close enough to downtown without being in the middle of downtown. We will stay again! "
"Mermaid House" in Downtown Mt. Dora!! Pet Friendly

Heated Pool house in Lake Panasoffkee

9.6 out of 10, Exceptional, (31)
"I like every room ,the pool, and everything "
The price is £276
includes taxes & fees
2 Jul - 3 Jul
Heated Pool house in Lake Panasoffkee

BRAND NEW 2 BDR 2 BTH w. Golf Cart - Half mile to EASTPORT

10.0 out of 10, Exceptional, (52)
"Would definitely stay there again"
BRAND NEW 2 BDR 2 BTH w. Golf Cart - Half mile to EASTPORT

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

10.0 out of 10, Exceptional, (92)
"Loved The Villages!! This villa was great! Cant wait to come back. "
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!

10.0 out of 10, Exceptional, (32)
"We had a wonderful weekend. Great spot v"
1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!

Perfect Location Between Brownwood & Lake Sumter

9.8 out of 10, Exceptional, (103)
"Property was very nice! A few minor issues that were corrected. The location and neighborhood were great. Would recommend!"
Perfect Location Between Brownwood & Lake Sumter

Walk to Spanish Springs, free 4 seater golf cart, covered patio! Pools nearby!!

9.6 out of 10, Exceptional, (62)
"Had great time..will definitely stay again"
Walk to Spanish Springs, free 4 seater golf cart, covered patio! Pools nearby!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Can I find a holiday rental in Leesburg?

Yes, there are holiday rentals close to the most popular sights in Leesburg, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and scenic lakeside in Leesburg. The live music and festivals are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Leesburg has to offer?

2 King 2 Twin 1 Queen Enormous Deck 3 BD Lakeview House at Waterfront Park: This holiday home rental outside of Leesburg is located on a lake, and offers a balcony, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Leesburg?

Expedia has 33 holiday rentals for your stay in Leesburg.

What can I see and do in Leesburg?

Enjoy the outdoors at Venetian Gardens and Treasure Island, or simply take in cultural attractions like Leesburg Center for the Arts and Paquette's Historical Farmall Museum. Lake Griffin and Plantation Golf Club are other places to visit while you're in town.

What are holiday rentals like in Leesburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Leesburg. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip.