Holiday houses in Leesburg

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Top-rated holiday rentals in Leesburg

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Guest favourite
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, 125 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 favourite
A compact living area features a light-colored sofa with decorative pillows. A small dining table and two chairs are positioned nearby. The kitchen is equipped with cabinets and appliances, and warm lighting creates an inviting atmosphere.
Apartment in Leesburg
5 out of 5 average rating, 55 reviews

Downtown Leesburg Owners Suite

Take it easy at this unique and tranquil getaway. Walk to downtown restaurants and festivities. Take a walk around the pond at Fountain Lake Park. Relax under a plush outdoor living space with provided grilling and dining area. NOT Lakefront, But This apartment is a short 1/2 block stroll from Downtown Leesburg, including Dining, Pubs, Shops and Craft Beer houses. Just a few blocks from Beacon College, UF Health Hospital, downtown entertainment and just a half mile walk to beautiful Lake Harris

Top Guest favourite
An open living space features a cozy sleeping area and a small dining arrangement. Wooden beams highlight the ceiling above. Natural light enters through the door and windows, while a television and kitchenette with appliances are visible against the walls.
Apartment in Lady Lake
5 out of 5 average rating, 19 reviews

Desperado 2 - Cozy Peaceful Apt. Lady Lake FL.

Escape to your unique and private 2nd story apartment nestled on 2 acres of serene land and just a short 7-minute drive to The Villages. Enjoy the tranquility of nature while still being close to vibrant entertainment, shopping and dining options. Your cozy and well appointed space offers the perfect blend of seclusion and convenience making it an ideal getaway for relaxation and rejuvenation. *perfect for vacation *perfect for traveling workers *perfect for visiting family in the The Villages

Top Guest favourite
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, 325 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 favourite
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, 412 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 favourite
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, 158 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 favourite
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, 125 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 favourite
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!

Guest favourite
A shaded gazebo with wooden seating is positioned on a concrete slab, surrounded by lush green grass. The cabin features a brown exterior and a welcoming porch, framed by trees and Spanish moss, offering a serene and natural setting.
Cabin in Leesburg
4.78 out of 5 average rating, 18 reviews

Lakefront Magic Wilderness Cabin

Make some forever memories at this unique and family-friendly place! Nestled on an acre of oak and cypress forest, The Magic Wilderness Cabin evokes the timeless beauty of early Florida lake life with a whimsical nod to it's original beginnings at a world famous theme park. The Magic Wilderness Cabin welcomes you to delight in the quiet nature of beautiful Lake Harris and the Harris chain while watching the sunset over the the scenic shores of the lake from our private dock

Top Guest favourite
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, 161 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 favourite
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, 106 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 favourite
Cottage in Coleman
4.96 out of 5 average rating, 167 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.

Popular amenities for Leesburg holiday rentals

When is the best time to visit Leesburg?

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Avg. price$267 NZD$265 NZD$265 NZD$230 NZD$215 NZD$196 NZD$208 NZD$203 NZD$203 NZD$205 NZD$221 NZD$224 NZD
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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 holiday rentals in Leesburg

  • Total holiday rentals

    Explore 200 holiday rentals in Leesburg

  • Nightly prices starting at

    Leesburg holiday rentals start at $53 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    200 of Leesburg holiday 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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