Holiday Homes in Leesburg

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Leesburg

Our top choices for Leesburg holiday homes

"Mermaid House" in Downtown Mt. Dora!! Pet Friendly
Terrace/patio

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

9.8 out of 10, Exceptional, (66)
"Really liked the property, it was very cute. Some minor issues like non-functioning TV's and would have been nice to have some ice in the freezer, but overall it was nice and clean and I would stay again!"
"Mermaid House" in Downtown Mt. Dora!! Pet Friendly
Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square
Fridge, microwave, oven, stovetop

Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

10.0 out of 10, Exceptional, (107)
"Great landlords, beautiful villa and great location "
Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square
Modern Comfort & Prime Location in The Villages – Golf Cart Included!
Smart TV

Modern Comfort & Prime Location in The Villages – Golf Cart Included!

10.0 out of 10, Exceptional, (70)
"We had a wonderful stay at this hidden gem in The Villages! The location was perfect — close to everything we needed — and having the golf cart was a huge bonus. The home was clean, cozy, and had everything we needed for a relaxing getaway. We would definitely stay again!"
Modern Comfort & Prime Location in The Villages – Golf Cart Included!
Dora Splash Pad
Property grounds

Dora Splash Pad

9.8 out of 10, Exceptional, (114)
"Cannot say enough how great this vacay was. Such a relaxing stay, enough to not even want to leave the house. So many great memories made "
Dora Splash Pad
Perfect location! 3b2bFree golf cart! Minutes to Lake Sumter&Spanish Springs
Fridge, microwave, oven, stovetop

Perfect location! 3b2bFree golf cart! Minutes to Lake Sumter&Spanish Springs

9.6 out of 10, Exceptional, (70)
"The house fit our needs perfectly. It was very clean, in a nice, quiet neighborhood. The TV's were nice with many viewing options. It was close to Spanish Springs and Lake Sumter Landing town squares making it easy to get around. Definitely would recommend. "
Perfect location! 3b2bFree golf cart! Minutes to Lake Sumter&Spanish Springs
European meets Southern Charm in this 3 Bedroom Get Away in Mount Dora
Smart TV, DVD player, ping pong, books

European meets Southern Charm in this 3 Bedroom Get Away in Mount Dora

9.8 out of 10, Exceptional, (144)
"This was a very comfortable stay. The house is nicely appointed. Very easy to relax. The pool and pool area are nice. Only drawback is it isn't heated."
European meets Southern Charm in this 3 Bedroom Get Away in Mount Dora
1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!
Smart TV

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

10.0 out of 10, Exceptional, (34)
"Amazing property. "
The price is AU$376
includes taxes & fees
24 Aug - 25 Aug
1 min walk to Downtown! Outdoor Patio! 5 star luxury! Golf Cart Rental!
2 King 2 Twin 1 Queen Enormous Deck 3 BD Lakeview House at Waterfront Park
Terrace/patio

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

10.0 out of 10, Exceptional, (17)
"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."
2 King 2 Twin 1 Queen Enormous Deck 3 BD Lakeview House at Waterfront Park
Cozy Country Home 4 Blocks From the Lake
Exterior

Cozy Country Home 4 Blocks From the Lake

9.6 out of 10, Exceptional, (84)
"Great location ..cute place ..comes with snacks and coffee cups which is great "
Cozy Country Home 4 Blocks From the Lake
The Rose on Lakeside Mount Dora-Umatilla 4 Bedrooms 2 1/2 bathrooms Sleeps 10
Outdoor dining

The Rose on Lakeside Mount Dora-Umatilla 4 Bedrooms 2 1/2 bathrooms Sleeps 10

10.0 out of 10, Exceptional, (35)
"Our family enjoyed a very comfortable stay! Wonderful accommodations!"
The price is AU$521
includes taxes & fees
24 Aug - 25 Aug
The Rose on Lakeside Mount Dora-Umatilla 4 Bedrooms 2 1/2 bathrooms Sleeps 10
Sunset Cove In the Village of St. John
Exterior

Sunset Cove In the Village of St. John

10.0 out of 10, Exceptional, (36)
"We had a very nice stay here. The house was very comfortable and had all we needed, and we enjoyed using the golf cart to explore the Villages."
Sunset Cove In the Village of St. John
LUXURY ESCAPE-Better Than a 5-Star Hotel: 2 Bed/1 Bath/ Encl Lanai w/ Heat & A/C
Smart TV

LUXURY ESCAPE-Better Than a 5-Star Hotel: 2 Bed/1 Bath/ Encl Lanai w/ Heat & A/C

2.0 star property
10.0 out of 10, Exceptional, (24)
"The property is in a great location for everything you need in the villages and the surrounding area. Very clean and comfortable with a nice sitting area in the patio outside. Communications with the owner is very helpful and also quick to respond. Very safe area to stay. "
The price is AU$419
includes taxes & fees
24 Aug - 25 Aug
LUXURY ESCAPE-Better Than a 5-Star Hotel: 2 Bed/1 Bath/ Encl Lanai w/ Heat & A/C
Private Spacious Room in Home, with Pool-The Oasis Room
Outdoor pool

Private Spacious Room in Home, with Pool-The Oasis Room

9.6 out of 10, Exceptional, (17)
" It a wonderful place "
The price is AU$171
includes taxes & fees
23 Aug - 24 Aug
Private Spacious Room in Home, with Pool-The Oasis Room
Cozy Beach Style Attached Apartment Studio
Terrace/patio

Cozy Beach Style Attached Apartment Studio

9.4 out of 10, Exceptional, (32)
"Very nice set up having TV’s in both rooms was very nice. "
Cozy Beach Style Attached Apartment Studio
Private Pool, Golf Cart, & Pet Friendly. Close to Golf and Town Squares.
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (3)
"Great place in a very convenient location "
Private Pool, Golf Cart, & Pet Friendly. Close to Golf and Town Squares.
Heated Pool house in Lake Panasoffkee
Outdoor dining

Heated Pool house in Lake Panasoffkee

9.6 out of 10, Exceptional, (37)
"Great clean house, thanks for having us!"
The price is AU$573
includes taxes & fees
31 Aug - 1 Sept
Heated Pool house in Lake Panasoffkee
Cozy, Close to downtown Lake View home.
Property grounds

Cozy, Close to downtown Lake View home.

9.6 out of 10, Exceptional, (16)
"House was clean and organized. Fun view of the lake!"
Cozy, Close to downtown Lake View home.
1887 Royellou House 3BR 2BA
Dining

1887 Royellou House 3BR 2BA

10.0 out of 10, Exceptional, (155)
"Property was well appointed and within walking distance to downtown. "
1887 Royellou House 3BR 2BA
PETS STAY FREE Canal Front 3 bed/2 bath single family ample parking
Property grounds

PETS STAY FREE Canal Front 3 bed/2 bath single family ample parking

9.4 out of 10, Exceptional, (28)
"Great place to catch up with friends and relax"
The price is AU$445
includes taxes & fees
22 Sept - 23 Sept
PETS STAY FREE Canal Front 3 bed/2 bath single family ample parking
Closest Stay to Downtown Mt Dora - Renovated - Walk Everywhere - 5-Star Reviews
Fridge, microwave, oven, stovetop

Closest Stay to Downtown Mt Dora - Renovated - Walk Everywhere - 5-Star Reviews

10.0 out of 10, Exceptional, (31)
"Beautiful decorated and a very cozy place. We would definitely come back again "
The price is AU$589
includes taxes & fees
26 Aug - 27 Aug
Closest Stay to Downtown Mt Dora - Renovated - Walk Everywhere - 5-Star Reviews
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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Top Leesburg Hotel Reviews

The Waterfront Inn

The Waterfront Inn

10/10 Excellent
"Stop over from a road trip in the mountains. We stayed 1 night with our traveling pup, and I’m glad we stayed here. The room was clean, spacious and I loved the laminate flooring. The shower was wonderful! Bed and pillows were nice and comfy. Good pet friendly place. The restaurant was okay, it has a nice view and the patio would be nice to sit out if it was cooler out. Pool looked wonderful too. Would definitely stay again!"
Darlene 1-night trip
Posted 20 hours ago
The Waterfront Inn