House
10.0(40 Reviews)
2 Bedrooms
4 Guests
Parking
Pool
Kitchen
Air Conditioner
US $268/Night
7 Nights - US $1,877
Leesburg, FL Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Leesburg
10.0
Villa
10.0(9 Reviews)
2 Bedrooms
6 Guests
- Parking
View- Kitchen
- Air Conditioner
US $217/Night
7 Nights - US $1,516
House
3 Bedrooms
6 Guests
Hot Tub- Parking
- Pool
Balcony/Terrace
US $437/Night
7 Nights - US $3,056
House
10.0(16 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $221/Night
7 Nights - US $1,549
House
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
Internet
Pet Friendly
US $140/Night
7 Nights - US $980
House
10.0(15 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $208/Night
7 Nights - US $1,457
House
10.0(15 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,304
House
10.0(12 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $200/Night
7 Nights - US $1,402
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $180/Night
7 Nights - US $1,261
Luxury Holiday Rentals in Leesburg
Over 3535+ Luxury Holiday Rentals in or Near Leesburg
Unlock the Best Price
House
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $9,921/Night
7 Nights - US $69,445
House
8.0(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $4,634/Night
7 Nights - US $32,436
US $2,067/Night
7 Nights - US $14,468
House
3.0(1 Review)
5 Bedrooms
14 Guests
- Parking
- Air Conditioner
- Internet
Bedding/Linens
US $1,764/Night
7 Nights - US $12,346
New
House
5 Bedrooms
28 Guests
Private Pool- Parking
- Pool
- Balcony/Terrace
US $1,591/Night
7 Nights - US $11,134
US $1,587/Night
7 Nights - US $11,112
House
9.0(31 Reviews)
7 Bedrooms
16 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,116/Night
7 Nights - US $7,809
House
9.8(31 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,111/Night
7 Nights - US $7,779
Top-Rated Holiday Rentals with a Pool in Leesburg
Over 1956+ The Best Private Villas and Holiday Rentals in Leesburg with a Pool
House
10.0(234 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $262/Night
7 Nights - US $1,831
House
10.0(134 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $185/Night
7 Nights - US $1,293
House
10.0(133 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $201/Night
7 Nights - US $1,404
House
10.0(130 Reviews)
3 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- View
- Kitchen
US $180/Night
7 Nights - US $1,258
House
10.0(128 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
Ocean View
US $167/Night
7 Nights - US $1,171
House
10.0(118 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
Breakfast- Parking
- Pool
US $208/Night
7 Nights - US $1,454
Villa
10.0(114 Reviews)
2 Bedrooms
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $181/Night
7 Nights - US $1,265
House
10.0(110 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $327/Night
7 Nights - US $2,291
House
10.0(99 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $242/Night
7 Nights - US $1,694
Pet-Friendly Holiday Rentals in Leesburg
Over 1386+ Pet-Friendly Holiday Rentals in or Near Leesburg
Villa
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $205/Night
7 Nights - US $1,434
Villa
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $349/Night
7 Nights - US $2,443
Cottage
10.0(5 Reviews)
1 Bedroom
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $375/Night
7 Nights - US $2,624
House
10.0(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $311/Night
7 Nights - US $2,180
House
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $334/Night
7 Nights - US $2,336
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $246/Night
7 Nights - US $1,724
Villa
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $215/Night
7 Nights - US $1,502
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $213/Night
7 Nights - US $1,488
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $118/Night
7 Nights - US $824
Large Holiday Rentals and Private Villas in Leesburg
Over 571+ Large Holiday Rentals and Private Villas in or Near Leesburg
Villa
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $172/Night
7 Nights - US $1,207
Villa
10.0(4 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $377/Night
7 Nights - US $2,636
Villa
10.0(1 Review)
1 Bedroom
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $105/Night
7 Nights - US $735
Villa
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $149/Night
7 Nights - US $1,044
Villa
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Pool
- Air Conditioner
- Internet
Barbecue/Outdoor Cooking
US $165/Night
7 Nights - US $1,155
Villa
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $266/Night
7 Nights - US $1,862
Villa
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $243/Night
7 Nights - US $1,702
Villa
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $225/Night
7 Nights - US $1,578
Villa
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $210/Night
7 Nights - US $1,473
Wheelchair Accessible Holiday Homes in Leesburg
Over 75+ Wheelchair Accessible Holiday Homes in or Near Leesburg
House
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $314/Night
7 Nights - US $2,196
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $220/Night
7 Nights - US $1,539
US $169/Night
7 Nights - US $1,183
House
9.6(24 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $476/Night
7 Nights - US $3,335
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $244/Night
7 Nights - US $1,710
House
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $279/Night
7 Nights - US $1,951
House
10.0(15 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $191/Night
7 Nights - US $1,334
House
9.8(30 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $425/Night
7 Nights - US $2,977
House
10.0(53 Reviews)
3 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $305/Night
7 Nights - US $2,137
Leesburg Private Villas and Holiday Homes Under $200
Over 1743+ Leesburg Private Villas and Holiday Homes Under $200
House
10.0(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $182/Night
7 Nights - US $1,273
House
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
Spa- Balcony/Terrace
US $162/Night
7 Nights - US $1,135
US $169/Night
7 Nights - US $1,185
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $198/Night
7 Nights - US $1,385
US $160/Night
7 Nights - US $1,120
Villa
10.0(1 Review)
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $193/Night
7 Nights - US $1,348
US $136/Night
7 Nights - US $952
House
9.8(11 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $185/Night
7 Nights - US $1,292
Villa
9.6(5 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $198/Night
7 Nights - US $1,388
Instantly Bookable Holiday Homes in Leesburg
Over 1936+ Instantly Bookable Holiday Homes in or Near Leesburg
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $272/Night
7 Nights - US $1,907
US $141/Night
7 Nights - US $986
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $216/Night
7 Nights - US $1,509
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $318/Night
7 Nights - US $2,226
House
9.6(25 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $224/Night
7 Nights - US $1,570
Villa
9.0(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $243/Night
7 Nights - US $1,702
Villa
8.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $253/Night
7 Nights - US $1,770
House
8.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $196/Night
7 Nights - US $1,370
House
6.0(1 Review)
2 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $187/Night
7 Nights - US $1,309
Book a Last Minute Place to Stay in Leesburg
About Casai's Private Villas and Holiday Rentals in Leesburg
Discover more than 3544 vacation rentals available in Leesburg. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Leesburg.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Leesburg, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Leesburg. On average, places to stay near Leesburg offer 1494.62 ft², with nightly prices averaging US $232.
With Casai, finding and comparing holiday rentals in Leesburg is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Leesburg, FL
There are 3544 Leesburg, FL Holiday Rentals
- Prices for a holiday home in Leesburg start at US $26
- Top rated vacation home in Leesburg is Quaint Private Cottage in Residential Mount Dora - 1/2 mile from downtown
- Most popular short term in Leesburg is Brownwood Hotel & Spa
- Cheapest place to stay in Leesburg is Cozy Retreat in Southern Oaks
- Most expensive holiday rental in Leesburg is Your Happy Place #1
Recently Booked Holiday Rentals in Leesburg
Frequently Asked Questions About Leesburg?
What are the top holiday rentals in Leesburg?
With numerous options available in Leesburg, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Leesburg:
- Quaint Private Cottage in Residential Mount Dora - 1/2 mile from downtown
- Historic District's Crescent Moon Cottage
- June-July Special Discount Offer: Golf-Front Home, Solar Pool, Free Cart & WiFi
- All In The Details: Modern Amenities, Close to Downtown. Pet Friendly!
- Fox Haven Cottage - A cozy one bedroom cottage
- High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
- Historic District Bungalow - Easy Walk to Downtown
- Pet Friendly-Walk to Sumter Landing! Our Village Gem -10 Star -Golf Cart
- Entire 3 Bedroom Home in The Villages - Sleeps 10
- Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages.
How many holiday rentals have private pools in Leesburg?
Discover a selection of holiday rentals with private pools near Leesburg with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Leesburg are best for families?
If you're searching for a family-friendly holiday home in Leesburg, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Leesburg:
How many Casai.nz holiday rentals are available in Leesburg?
As of 2026, Casai boasts over 3544 properties listed in the Leesburg area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Leesburg.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Duval Vacation Rentals in Leesburg, Florida | 34 |
| Liberty Park Vacation Rentals in Leesburg, Florida | 30 |
| Lynnhaven Vacation Rentals in Leesburg, Florida | 28 |
| Mallory Square Vacation Rentals in Leesburg, Florida | 26 |
| Virginia Trace Vacation Rentals in Leesburg, Florida | 1032 |
| Collier Vacation Rentals in Leesburg, Florida | 799 |
| Lake Sumter Landing Vacation Rentals in Leesburg, Florida | 1121 |
| Charlotte Vacation Rentals in Leesburg, Florida | 668 |
| Hemingway Vacation Rentals in Leesburg, Florida | 854 |
| Fernandina Vacation Rentals in Leesburg, Florida | 819 |
| Caroline Vacation Rentals in Leesburg, Florida | 917 |
| Piedmont Vacation Rentals in Leesburg, Florida | 484 |
| Bonita Vacation Rentals in Leesburg, Florida | 890 |
| Del Mar Vacation Rentals in Leesburg, Florida | 697 |
| Sabal Chase Vacation Rentals in Leesburg, Florida | 1004 |
| Gilchrist Vacation Rentals in Leesburg, Florida | 844 |
