We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Leesburg House Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $305 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Leesburg area holiday rental. You're so close to securing your perfect getaway. Book today.
    29 Matching Rentals in the Leesburg AreaView all 55 rentals
    Sort by:
    Default
    Leesburg
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Leesburg
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Leesburg
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 15 kilometres of Leesburg.
    3/2 1920s Lake Estate w/Access to Pool, Gym & Boat1 / 50
    (3)Very good
    Yalaha
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 December 2016
    My family and I (6 of us including two children) stayed for 4 days and loved the quiet of this house. We enjoyed sitting by the lake, the Yalaha bakery, the Dora Canal cruise...
    Reviewed 15 August 2016
    We travelled to Florida with our 3 children (12-18), mainly to "do the attractions" but also see a bit more of the US than just staying in a hotel.This house was ideal...
    See all reviews
    About this property
    Bring your boat or enjoy the views from the land, this gorgeous lake house has it all! Built from Cypress cut from the property, this house was home to the original settlers of the area. Fully remodeled in 2013, the 1920s charm is still present throughout. Decorated in Florida Nautical/Lodge style,...
    View all property information
    Location Information
    Yalaha, Lake County 34797
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    Lady Lake
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Porch
    • Patio
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home has a Great location! The home features Master Suite with King size new comfortable bed and private bath and TV. Guest Bedroom has Queen size bed with walk-in closet. Rooms have Vaulted ceilings, it has a Gorgeous New Kitchen with breakfast bar, and a beautiful dining set. There is...
    View all property information
    Location Information
    Lady Lake, Lake County 32159
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Howey in the Hills
    10 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Parking
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Key features 8000 sq ft 10 themed bedrooms 6 bathrooms Sleeps 24 Theme park Private pool and...
    View all property information
    Location Information
    Howey in the Hills, Lake County 34715
    Holiday Rental House - 10 Bedrooms, 6 Bathrooms, Sleeps 24
    Make Enquiry
    Grand Island, FL
    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to...
    View all property information
    Location Information
    Grand Island, Florida 34747
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 16
    Make Enquiry
    Lady Lake
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Porch
    • Patio
    • Washer
    • Wi-Fi
    • Housekeeping Included
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful house is among the grand oak trees in the heart of America's premier 400 acre Equestrian Resort in sunny Central Florida. Additional amenities include a covered carport and a Florida sunroom. Amenities include Golf Carts, world famous Carriage Museum, “The Bistro” with a...
    View all property information
    Location Information
    Lady Lake, Lake County 32195
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Lady Lake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Air Conditioning
    • Porch
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities include Golf Carts, world famous Carriage Museum, “The Bistro” with a fully-stocked bar & live weekend entertainment, Hair Salon, Massage Therapist, miles of walking and bicycling trails, Sunday service in our Chapel, Horseback & Carriage Rides on property, tennis court, fishing, equine...
    View all property information
    Location Information
    Lady Lake, Lake County 32195
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Mid Florida, FL
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to...
    View all property information
    Location Information
    Mid Florida, Florida 34747
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Save time - get the best Leesburg rentals sent straight to your email!
    Get the List
    LOCATION, conveniently located between Lake Sumter Landing and Brownwood Paddock1 / 7
    (1)Excellent
    Fruitland Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 December 2017
    Lovely home. Very spacious and comfortable. There is so much to do in the area. Lots of great restaurants and entertainment in The Villages. Nightly music in the squares is...
    See all reviews
    About this property
    This spacious villa is located in the neighborhood of Hadley and is conveniently located between Lake Sumter Landing Market Square and Brownwood at Paddock Park. This is where you'll find restaurants, shopping, theaters, FREE live music and dancing every night. About 5 miles up the road you'll find...
    View all property information
    Location Information
    Fruitland Park, Lake County 32162
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Fruitland Park
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MEMORIAL DAY SALE NOW ON. Up to 20% off (prices reflect discount). This beautifully decorated 3 bedroom, 2 bathroom Courtyard Villa in Jackson Villas in the Village of Pine Ridge is perfectly positioned for the many facets of The Villages' vacation lifestyle. Vasquez is equidistant from Brownwood...
    View all property information
    Location Information
    Fruitland Park, Lake County 32162
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Lady Lake
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful house is among the grand oak trees in the heart of America's premier 400 acre Equestrian Resort in sunny Central Florida. The Hilltop House has 1 King-sized bed & 1 pull-out sofa bed. Comfortably houses 4 guests. Full kitchen & bath. Amenities include Golf Carts, world famous...
    View all property information
    Location Information
    Lady Lake, Lake County 32195
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Mid Florida, FL
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Special Offer! Book today to enjoy exclusive extras unique to Top Villas! Free transfers to...
    View all property information
    Location Information
    Mid Florida, Florida 34747
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Make Enquiry
    Haines Creek, FL
    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview This 8 bedroom villa is located at the Encore Club, less than a 10 minute drive down the road to Walt Disney World and their 4 incredible theme parks! Conviently located for you and your loved ones to experience and enjoy, Walt Disney World's proximity from this vacation home is an added...
    View all property information
    Location Information
    Haines Creek, Florida 34747
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
    Make Enquiry
    Mid Florida, FL
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About Bayshore Beauty Bayshore Beauty is the vacation rental property you've been dreaming of for your Florida vacation. This luxury townhome has all the bells and whistles included, ensuring you won't have to lift a finger while relaxing on your trip. The large master suite boasts a king bed and...
    View all property information
    Location Information
    Mid Florida, Florida 32819
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Mid Florida, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedroom, 2 Bathroom Deluxe Condo at the Isle of Cay Commons in Vista Cay Resort Vista Cay Resort, Orlando Florida. Located In the newly developed area behind International Drive, at the heart of Orlando's Attraction and Convention Business District, Vista Cay’s location and accommodations have...
    View all property information
    Location Information
    Mid Florida, Florida 32819
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Wildwood, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “When it comes to eternity only three things matter... Location, Location, Location” Newly renovated with modern amenities and memory foam bedding. This central Florida home is your perfect retreat! Nestled on a 1.5 Acre lot, just off I-75 (6.8 Miles) near beautiful The Villages, FL (1/4 mile)....
    View all property information
    Location Information
    Wildwood, Florida 34785
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Mid Florida, FL
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Florida vacations will never be the same after you stay in the stunning lake view Sunset Retreat condo at Vista Cay Resort in Orlando. This 2-bedroom, 2-bath condo is elegantly furnished down to the last detail. The living area hosts deluxe leather furniture and entertainment center with...
    View all property information
    Location Information
    Mid Florida, Florida 32819
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Mid Florida, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedroom, 2 Bathroom Deluxe Condo at the Isle of Cay Commons in Vista Cay Resort Vista Cay Resort, Orlando Florida. Located In the newly developed area behind International Drive, at the heart of Orlando's Attraction and Convention Business District, Vista Cay’s location and accommodations have...
    View all property information
    Location Information
    Mid Florida, Florida 32819
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Mid Florida, FL
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Grill
    • Parking
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This completely renovated 3-story townhouse is a true paradise in the beautiful Vista Cay Resort. Enjoy all the amenities of the resort, including clubhouse with gym, spa and pool, and go home to your own private townhome with lots of space for everyone. This townhome is perfect for large...
    View all property information
    Location Information
    Mid Florida, Florida 32819
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Mid Florida, FL
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About Tropical Dreams Step into private luxury and rent the elegant Tropical Dreams townhome for your Florida vacation. This three-level property has plenty of space for everyone, and includes a covered one-car garage. The spacious living area has lots of comfortable seating and a home theater...
    View all property information
    Location Information
    Mid Florida, Florida 32819
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Mid Florida, FL
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely 3 story townhouse is located on Vista Cay Resort, a secure, gated community just off elegant Universal Blvd and within minutes of all the theme parks, Disney, shopping, restaurants and airport. Comfortably sleeps 8. New carpet and all new paint. Relax in the open-plan living space...
    View all property information
    Location Information
    Mid Florida, Florida 32819
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Fruitland Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully decorated 3 bedroom, 2 bathroom Courtyard Villa in Jackson Villas in the Village of Pine Ridge is perfectly positioned for the many facets of The Villages' vacation lifestyle. Vasquez is equidistant from Brownwood Paddock Square, modeled on the historic 'Cracker' (cattleman)...
    View all property information
    Location Information
    Fruitland Park, Lake County 32162
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Fruitland Park
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Terrace
    • Washer
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This new 2 bedroom, 2 bathroom home sleeps 5, has a complimentary golf cart for the duration of your Vacation stay, and is the Courtyard Villa model, one of the most popular Villages' designs , offering a very private enclosed back garden. The new Village of Pine Ridge is an excellent location,...
    View all property information
    Location Information
    Fruitland Park, Lake County 32163
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Wildwood, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan for your next getaway to take you to this beautiful 3-bedroom, 2-bathroom vacation rental house in The Villages, Florida! With almost 2,000 square feet of living space and a screened-in lanai, this home, in a fantastic location within the Village of Hillsborough and less than 2 miles from...
    View all property information
    Location Information
    Wildwood, Florida 34785
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Mid Florida, FL
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely 3 story townhouse is located on Vista Cay Resort, a secure, gated community just off elegant Universal Blvd and within minutes of all the theme parks, Disney, shopping, restaurants and airport. Comfortably sleeps 8. New carpet and all new paint. Relax in the open-plan living space...
    View all property information
    Location Information
    Mid Florida, Florida 32819
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Howey in the Hills
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note this property is at The Howey Mansion where daily tours are conducted; tours will not be taken through the guesthouse* If you're looking for an exclusive retreat, don't miss out on the opportunity to stay at this 2-bedroom, 1-bathroom vacation rental house at the historic Howey...
    View all property information
    Location Information
    Howey in the Hills, Lake County 34737
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Lady Lake
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The peaceful Villages Country Club offers more amenities than you could imagine, from archery to tennis courts, a private pool, golfing, and more! This cozy 2 bedroom, 2 bath vacation rental home accommodates 4 guests, perfect for small groups and families looking to get away. Start planning your...
    View all property information
    Location Information
    Lady Lake, Lake County 32159
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property
    Owner log in