Vacation rentals in Leesburg

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Top-rated vacation rentals in Leesburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.
Home in Lady Lake
4.96 out of 5 average rating, 327 reviews

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

Top guest favorite
The exterior of a single-story villa is depicted, featuring a light-colored stucco facade and a two-car garage. Paved driveway curves towards the entrance, with decorative landscaping including a potted plant and stone accents. Windows are adorned with decorative arches, enhancing curb appeal.
Home in The Villages
4.95 out of 5 average rating, 154 reviews

Remodeled 2/2 Baja style villa w/4 person cart

4 person, yamaha gas golfcart offered at this baja style 1000 sqft 2BR, 2BA courtyard villa! It comes fully furnished with pots, pans, linens, and does have a blow dryer and keurig! located in the De La Vista South area just off Morse, this villa is just a short cart ride to Spanish Springs or Sumter Landing. The villa has new stainless appliances, beautiful plank flooring, and fresh paint. King bed in the master, queen bed in the guest bedroom. All bedrooms have smart TV's, cable in LR only

Top guest favorite
The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.
Guesthouse in Leesburg
4.98 out of 5 average rating, 413 reviews

Silver Lake Guest Pool House Very Private !

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

Top guest favorite
An outdoor patio area features a screened enclosure with a private swimming pool. Comfortable seating is arranged around the pool, and lush greenery surrounds the space, providing a serene environment. Potted plants add a touch of color, enhancing the tranquil setting.
Guesthouse in Deer Island
4.95 out of 5 average rating, 130 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

On 5 beautiful wooded acres with a boat dock on the canal. Relax by the shared pool, enjoy a BBQ by the firepit, fish from the boat dock, enjoy nature, or simply read a book in the gazebo. Sapphire Cottage has a Master with a queen size bed, a fully equipped kitchen, 2 full size sofa-beds, dinning area for 6, and a full size bathroom. Whether you are looking to relax, enjoy the farm animals, or a bit of adventure we have the perfect location. We live in the main house across the cottage.

Guest favorite
A wooden dock extends into the calm waters, surrounded by lush greenery and mature trees. Steps lead up from the dock to a cottage nestled among the foliage, offering a serene and natural setting.
Cottage in Leesburg
4.91 out of 5 average rating, 113 reviews

Waterfront Cottage on The Harris Chain in Leesburg

Cozy waterfront cottage on Haynes Creek. Whether its relaxing, fishing from your own dock, boating the Harris chain, paddle boarding, birdwatching, use our kayaks or pedal boat, or exploring the nearby towns and springs... we have it all. Fully equip kitchen, outdoor grilling area, wifi and cable, parking, laundry, gas fire pit on your private deck, boat parking at your dock or book a tour with Monster Bass fishing. Walkable to nearby stores or Gator Bay for a drink, meal, or music!

Top guest favorite
The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.
Home in The Villages
4.97 out of 5 average rating, 99 reviews

Fabulous Courtyard Villa close to Sumter Landing

This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

Top guest favorite
A cozy living space features a large television mounted on the wall and a wooden dresser. In the foreground, two bar stools are positioned by a counter. The kitchen area is visible in the background, showcasing wooden cabinetry and a tile backsplash.
Guesthouse in Tavares
4.98 out of 5 average rating, 131 reviews

The Landing Pad+Short Stroll to Heart of Tavares!

We are located in heart of Taveras where everything is walking distance-restaurants, pubs, the seaport, Wooton Park & the history museum! Sit on the patio while using the electric grill. Bring your boat! Plenty of off street park with easy access using the alleyway. Bathroom has a rain shower with 2 speeds. Full kitchen including all the basic amenities+kureig with refillable cups. Come & relax at this fun little spot & enjoy all we have to offer thanks for landing here!

Top guest favorite
Aerial view of The Faith Estate, showcasing the historic Victorian-style house surrounded by lush greenery and expansive lawns. The blue exterior contrasts with the vibrant landscape, while serene lake waters reflect the soft colors of the sunset sky, enhancing the natural beauty of the setting.
Home in Leesburg
4.89 out of 5 average rating, 149 reviews

The Faith Estate - A Lakefront Storybook House

Welcome to The Faith Estate, a historic 5-bedroom, 3.5-bathroom lake house in Leesburg, FL, near The Villages, Eustis, and Mount Dora. Perfect for reunions, retreats, or a relaxing getaway. Ideal for boaters, with space for multiple boats and trailers—great for Harris Chain of Lakes events. The estate also allows approved events. Submit details via Airbnb for approval before check-in. Unapproved events are not permitted. Event setups must respect property guidelines.

Top guest favorite
A wooden dock extends over calm waters, framed by lush greenery and moss-draped trees. The tranquil scene is complemented by a screened dockhouse nearby, providing a secluded spot for relaxation and enjoying the natural surroundings.
Cottage in Floral City
4.94 out of 5 average rating, 216 reviews

Waterfront Cottage 2BR 1B

This charming house is located on nearly an acre of woodland. Fish from the dock of the screen room on the canal or kayak to the nearby lake. Relax in the private backyard Jacuzzi. Bike on the nearby Withlacoochee Trail. There are 2 bedrooms plus living room sleeper sofa, and a lanai with a day bed. Fully furnished. Orlando theme parks are 1 1/2 hour away, Busch Gardens 1 hour. Close to Weeki Wachee, Homosassa and Crystal River for manatee viewing or scallop season.

Top guest favorite
An open-concept living area features natural light streaming through large windows with scenic views of the lake. Cozy seating arrangements include a comfortable sectional and accent chairs, complemented by a dining space and a well-equipped kitchen with modern appliances.
Home in Tavares
4.96 out of 5 average rating, 110 reviews

Lake Dora Dream-Waterfront/Pool

Luxurious lakefront home on Lake Dora - 8 minutes to downtown Mount Dora and Tavares. Enjoy your vacation in this newly renovated pool home (Pool Not Heated) on Lake Dora and the Harris chain of Lakes. Bring your boat or rent one nearby to explore the area by water and cruise the Dora Canal to Lake Eustis. Included is a guest apartment with private entrance totaling 4 bedrooms and 4 full baths. Just a half mile to the Tavares Pavilion and dining in downtown Tavares.

Top guest favorite
Cottage in Coleman
4.96 out of 5 average rating, 170 reviews

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.

Top guest favorite
A charming cottage is showcased, featuring a light-colored exterior with red shutters. The entrance is framed by a covered porch and planters, while a landscaped area with low shrubs and flowers adds a welcoming touch to the pathway.
Cottage in Eustis
4.94 out of 5 average rating, 106 reviews

Anneliese's Cottage

Just a delightful walk from Lake Eustis and its quaint downtown shopping & dining district, a 10 minute drive to Historic downtown Mt. Dora, and less than an hour from Orlando / Daytona Beach, this cottage , decorated with cozy elegance, is the perfect place to relax and truly enjoy all that the area has to offer. Right next door, you'll find an eclectic day spa, where you can set up a relaxing massage, facial, or have your hair & nails done during your stay!

Popular amenities for Leesburg vacation rentals

When is the best time to visit Leesburg?

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Frequently Asked Questions

  • Where should I stay in Leesburg?

    Make yourself at home in Leesburg by choosing from our most frequently booked neighborhoods. We have over 80 vacation rentals in Bassville Park, over 130 vacation rentals in Lisbon, and over 30 vacation rentals in Silver Lake.

  • Are there vacation rentals with a dedicated workspace in Leesburg?

    Yes! Work meets play with ease at over 100 vacation rentals in Leesburg featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Leesburg?

    Four-legged friends are welcome in Leesburg. Choose from more than 80 vacation rentals for guests traveling with pets.

  • Are there Leesburg vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Leesburg, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in apartment rentals in Leesburg?

    Experience the best of Leesburg with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Leesburg have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Leesburg. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Leesburg have wifi?

    Absolutely! We offer over 140 house rentals with wifi in Leesburg. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Leesburg have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Leesburg. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Leesburg have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Leesburg. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Leesburg?

    Leesburg has more than 120 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Leesburg

  • Total vacation rentals

    Explore 200 vacation rentals in Leesburg

  • Nightly prices starting at

    Leesburg vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 4,640 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    200 of Leesburg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Leesburg rentals

  • 4.8 Average rating

    Leesburg stays are highly rated by guests—averaging 4.8 out of 5!

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