Vacation rentals in Leesburg

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Top-rated vacation rentals in Leesburg

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Guest favorite
A set of wooden steps leads up to a charming cottage nestled among trees. The entrance features large glass doors, inviting natural light into the space. The surrounding area is landscaped, enhancing the tranquil ambiance of the private property.
Cottage in Eustis
4.95 out of 5 average rating, 122 reviews

Redbird cottage and farm. Equestrian lake cottage

Step back into “Old Florida” charm at this updated 1968 lake cottage, on a 7-acre equestrian farm. Secluded from main roads yet just minutes from downtown Mount Dora and Eustis, this peaceful retreat offers the perfect blend of rustic serenity and comfort. Located on a lake that offers direct water access. Campfires are welcomed, and the tranquil setting is made even more magical by the sight of horses. Inside, you'll find cozy touches and comfortable furnishings, including pillow-top mattresses

Top guest favorite
The exterior of a two-story detached home is presented, featuring white siding and black shutters. The entrance is adorned with planters, and a small walkway leads to the front door. Lush greenery surrounds the property, and a clear blue sky is visible above.
Cottage in Umatilla
4.98 out of 5 average rating, 113 reviews

Cottage by the Lake

Cute, comfortable 1935 detached home which is 900 SQUARE FEET AND PET FRIENDLY. Per pet fees are negotiable because we love them just message me: The other side of the property has our main home. The cottage is newly remodeled and fenced in. Views of Lake Umatilla from all rooms. 8 miles to beautiful Mount Dora and 3 miles to downtown Eustis. 1 hour to attractions, airport and east coast beaches. We are 20-30 minutes from most local Springs. Our Lake Umatilla does have public boat ramp access

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, 323 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 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, 407 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
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, 125 reviews

The Landing Pad+Short Stroll to Heart of Tavares!

LOW CLEANING FEES!!! 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!

Guest favorite
A tiny home is showcased with a grey exterior and a metal roof. Two wooden chairs are positioned on a grassy area in front, and flower pots add color near the entrance. Steps lead up to the front porch, providing access to the inviting interior.
Tiny home in Howey-in-the-Hills
4.96 out of 5 average rating, 153 reviews

Horse Farm- (2) Tiny Homes 33mi from Orlando

Rest & Relaxation at its finest! This Tiny Home is set to impress! Add on the natural beauty of the rolling hills of Howey, with some of Thee most impressive sunsets over the water & this becomes an Incredible Unique Stay! After sunset, enjoy a nice campfire in your firepit, as you STARGAZE into the night! This Tiny Home is fully equipped with ALL of your needs. Located on the back 3 acres of property, from which you will have your own Golf Cart to travel to/from our Designate Parking Area.

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, 127 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 charming green cottage is set among tall pine trees, featuring a wooden porch and a welcoming entrance. A small window is visible on one side, complemented by outdoor lighting. Bright flowers line the base of the cottage, enhancing its rural setting.
Tiny home in Groveland
4.95 out of 5 average rating, 120 reviews

Lovely Meadow Farm Cottage

This lovely farm cottage can be found in a secluded meadowland under various oaks and pines along a natural cypress dome. Spectacular star lit night skies accompanied by hooting owls, whippoorwills, and fire flies make for an unforgettable camp fire atmosphere. Amenities include an outdoor shower, washer, dryer, barbecue, fire pit, fishing and outdoor wrap around patio. Ponds, canals, and Florida wetland host a variety of birds, mammals, fish and reptiles including the Florida gator.

Guest favorite
An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.
Villa in The Villages
4.84 out of 5 average rating, 103 reviews

Location Can’t be Beat! With cart!

Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

Top guest favorite
A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.
Treehouse in St. Cloud
4.97 out of 5 average rating, 1,035 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Top guest favorite
Two cranes walk gracefully in shallow water at dusk, their reflections visible on the surface. A vibrant sunset fills the sky with shades of orange and purple, while soft clouds add texture to the scene. Lush greenery borders the water in the background.
Home in Leesburg
4.89 out of 5 average rating, 159 reviews

3-BR 2-BA house-amazing lake view and boat parking

Enjoy the tranquility of this lakefront getaway at Silver Lake in Leesburg, FL. This property is located in a secluded upscale residential neighborhood, yet still only few minutes away from SR 441, plenty of restaurants and the Lake Square Mall. Enjoy beautiful sunsets overseeing Silver Lake which is across the street from the house. Over 1 acre of land with lushful native trees and large lawn. Butterflies, birds, wildlife such as rabbits, and armadillos can be spotted.

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, 103 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.

Popular amenities for Leesburg vacation rentals

Quick stats about vacation rentals in Leesburg

  • Total rentals

    200 properties

  • Nightly prices starting at

    G$6,285 GYD before taxes and fees

  • Total number of reviews

    4.6K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    60 properties have a pool

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 130 vacation rentals in Lisbon, over 80 vacation rentals in Bassville Park, 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 90 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 70 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 $60 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 130 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 110 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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