Leesburg Holiday Rentals

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Holiday Rentals in Leesburg

Property grounds
The perfect place to rest. breakfast included
10.0 out of 10, Exceptional, (9)
"Arian and his wife are perfect hosts. The place was absolutely amazing. There was plenty of room for 1 or 2 people, with a private bedroom and bathroom. Exquisitely decorated with attention to every detail. Arian is a fabulous chef and gets your day started right with a wonderful breakfast. If I am in that area again, I know where I will be staying."
The price is NZ$233
includes taxes & fees
31 May - 1 Jun
The perfect place to rest. breakfast included
Exterior
Waterfront Cottage on the Harris chain in Leesburg
10.0 out of 10, Exceptional, (74)
"Very rustic looking on outside but beautifully decorated and clean inside. Double size bed took a little getting used to and kitchen table was small. Very nice walk-in shower.. Hosts were very helpful and provided some nice extras. We especially enjoyed sitting on the deck and looking out over the water at many different birds and some fishermen."
Waterfront Cottage on the Harris chain in Leesburg
Dining
Marilyn’s Romantic Getaway
10.0 out of 10, Exceptional, (42)
"House was very clean. Some shampoo… some soap and toothpaste supplied. Kitchen supplies…condiments , clothes detergent, toilet paper… you will need to buy. For any home in Villages… it would be good to better understand the golf cart paths… give more instruction. We used the maps app on our phone and put in for 🚲 since carts and bike paths are shared in The Villages. It took a a day or two to figure that out… not all roads are golf cart friendly. Mark was great about switching out the bikes...
Marilyn’s Romantic Getaway
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Property grounds
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart
10.0 out of 10, Exceptional, (6)
"Very lovely house. Loved the golf cart, only used our SUV 4 times in the 2 wks we were there."
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart
Fridge, microwave, oven, stovetop
BRAND NEW Dog Friendly 2/2 w. Golf Cart - Close to Activities, Shopping, Dining!
10.0 out of 10, Exceptional, (34)
"We had a wonderful time, the home beautiful, clean & very well equipped with everything you would need or want, right down to shampoo, conditioner & body wash in both bathrooms. We had a great time exploring all different areas on the golf cart which I’m sure was brand new. Lee & Mathis were super at getting back to us right away with any questions we had. We would definitely recommend renting this house. Thank you again Lee & Mathis for a wonderful holiday Tannis & Tom May 2024"
BRAND NEW Dog Friendly 2/2 w. Golf Cart - Close to Activities, Shopping, Dining!
Cozy Villages villa, 2 bed, 2 bath. Great Location
10.0 out of 10, Exceptional, (37)
"Really enjoyed staying here...."
Cozy Villages villa, 2 bed, 2 bath. Great Location
Fridge, microwave, oven, stovetop
Pool, Golf course view home with a golf cart
10.0 out of 10, Exceptional, (19)
"Great week"
Pool, Golf course view home with a golf cart
Fridge, microwave, oven, stovetop
Get Cozy in this newly renovated home by The Villages!
10.0 out of 10, Exceptional, (7)
"This house was VERY clean! Contact with property manager/owner was great! Adorable little neighborhood. Would definitely stay here again."
Get Cozy in this newly renovated home by The Villages!
Pool
Upto 45 Guests Sleep At This Unique Private Island 62 Acre Estate!
10.0 out of 10, Exceptional, (21)
"Great place with wonderful ownership and the most helpful staff. Definitely a place everyone should stay!!!"
Upto 45 Guests Sleep At This Unique Private Island 62 Acre Estate!
Fridge, microwave, oven, stovetop
Dog-friendly Summerfield home with a fenced-in yard, pool, hot tub, & games
10.0 out of 10, Exceptional, (7)
"Very nice house. Outdoor area and pool were wonderful. Loved the outdoor TV. Could use some more cooking dishware, but very minor issue. Would happily stay again."
Dog-friendly Summerfield home with a fenced-in yard, pool, hot tub, & games
Exterior
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
10.0 out of 10, Exceptional, (65)
"Very nice and clean very close to all of the amenities that the villages offer"
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
Pool
Vacation Home with luxurious pool in The Villages, Florida!
10.0 out of 10, Exceptional, (22)
"The house was immaculate and so lovely! We had a wonderful time! Can’t wait to come back again!"
The price is NZ$981
includes taxes & fees
23 May - 24 May
Vacation Home with luxurious pool in The Villages, Florida!
Fridge, microwave, oven, stovetop
"2 Bed, 2 Bath Gem in Village of Richmond - Serene Living!"
10.0 out of 10, Exceptional, (2)
"Super Cute and Quiet place. great for remote work. comfortable, well stocked. Nice bathrooms, plenty of towels. Clean. Comfortable bed, bonus having adjustable bed. Good TVs. Nice location. Minutes from Brownwood. I would go back for sure."
"2 Bed, 2 Bath Gem in Village of Richmond - Serene Living!"
Dining
Pet-Friendly Home w/ Lanai + Resort Amenities!
10.0 out of 10, Exceptional, (13)
"Great Location!"
Pet-Friendly Home w/ Lanai + Resort Amenities!
Property grounds
Walk To Brownwood Paddock Square, Restaurants & Nightly Entertainment
10.0 out of 10, Exceptional, (71)
"Adorable home, spotless and with all the amenities you need. The management company is also very responsive. Great location, too."
Walk To Brownwood Paddock Square, Restaurants & Nightly Entertainment
Outdoor dining
New log cabin ! Ocklawaha fl
10.0 out of 10, Exceptional, (64)
"My boyfriend and I were looking for a weekend getaway with our two German Shepherds. We found this beautiful log home!! It was beautifully decorated and it has an amazing dog friendly yard! Our puppies were free to play in the yard and explore while being completely secure. We would highly recommend and would love to stay again! The owner was very easy to contact and communicate with. 10/10 for sure! Very convenient to a lot of trails/forest for hiking if the heat cooperates!"
New log cabin ! Ocklawaha fl
Property grounds
Amazing three-bedroom home in The Villages. Great spot for a memorable vacation!
10.0 out of 10, Exceptional, (44)
"A great place to gather. Nice space and well appointed. Reasonably priced. Thank you Robert for making the home welcoming and fun to stay. We had many laughs and took many good memories from The Villages."
The price is NZ$787
includes taxes & fees
8 Jun - 9 Jun
Amazing three-bedroom home in The Villages. Great spot for a memorable vacation!
Indoor pool, outdoor pool
Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI
10.0 out of 10, Exceptional, (76)
"Everything we could hope for. It was immaculate. Close to golf, Spanish Springs, and shopping"
Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI
Fridge, microwave, stovetop, dishwasher
Sunny Florida Escape w/ Pool Access, Patio & Grill
10.0 out of 10, Exceptional, (6)
"The place was clean, well appointed, and came with concise instructions and info from the owner. Excellent!"
Sunny Florida Escape w/ Pool Access, Patio & Grill
Pool
FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!
10.0 out of 10, Exceptional, (32)
"We enjoyed everything about our stay. The location in The Villages was exactly what we were looking for. Communication with Brad was excellent. The property is well maintained and exactly as described. We look forward to returning soon!"
FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!
Don't see what you're looking for?
See all available properties in Leesburg
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.

Other types of properties in Leesburg you may be interested in

Property amenity
TownePlace Suites by Marriott Leesburg
2.5 star property
9.2 out of 10, Wonderful, (182)
"Pool and breakfast are nice."
The price is NZ$204
includes taxes & fees
30 May - 31 May
TownePlace Suites by Marriott Leesburg
Front of property - evening/night
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
2.0 star property
8.4 out of 10, Very good, (1001)
"Great place to stay. Very clean rooms. Staff is Freindly and always speaks to you when they see you, My granddaughter enjoyed the pool. Very relaxing. "
The price is NZ$146
includes taxes & fees
23 May - 24 May
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
Lobby
Best Western Plus Chain of Lakes Inn & Suites
2.5 star property
8.4 out of 10, Very good, (999)
"Great last minute stay! Well lit parking. Walking distance to a good restaurant, Ramshackles. They provide a nice variety of breakfast items."
The price is NZ$164
includes taxes & fees
26 May - 27 May
Best Western Plus Chain of Lakes Inn & Suites
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Leesburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Leesburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Leesburg. Seeing all the best attractions is bound to make you fall in love with Leesburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Leesburg short-term rentals, that won’t be hard to do.

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.

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 Paquette's Historical Farmall Museum and Paul P. Williams Auditorium. Lake Griffin and Lake Sumter Sports Complex and Recreation Area 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.

Recent reviews of Leesburg properties
Expedia verified reviews