
Family-friendly vacation rentals in Leesburg
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Leesburg
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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

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.

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

Solomon's porch entire apartment
Solomon's porch apartment is entire private 350 st ft apartment with bedroom, kitchenette, your own hallway and private bathroom. Solomon's porch apartment attached to main house.We are small Christian family that loves bible proverbs and named Airbnb after Solomon's wisdom. We have other listing that we are hosting since 2022. Our brand new house located between Ocala and The Villages. We are only few minutes from Santos mountain bike trails, horse park, National Forest and Silver Springs.

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.

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.

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.

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!

Duck Haven - Wildlife Sanctuary - 5 miles to I75
Have you ever wanted the opportunity to feed an egg to a fox? Or feed a lemur? Hand feed a deer or sheep? Dance with a cockatoo? If so you’ll get to have these and many more experiences here during your stay. Our Airbnb is different, and our main focus is on offering rememberal experiences to our guests. We have a small family run 501C-3 wildlife sanctuary here on our 18 acre facility that you will be staying at. We do live on the property, but in a detached house across the driveway

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.

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.

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 family-friendly rentals
Family-friendly home rentals with a hot tub

Spacious Bungalow with Private Pool and Courtyard

Villages-Private Heated Pool-Central Location

Lake View - 5 Miles to Disney!

Themed Home + Near Disney + Arcade + King Bed + Water Park + Spa

Spectacular! Disney/Universal Themed Home

*EPIC Tube Slide Bunk*FREE Pool Heat*5mi to Disney

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Ruby Oaks Farm w/ Beach Near St. JohnsRiver
Family- and pet-friendly home rentals

Peaceful Cottage in the Heart of Wildwood

Completely Private Suite w/ Pond, Grill & Kayak

Getaway on the Waterway: Kayak, SUP, fish, relax!

Beautiful House On the River, Kayaks, Large Dock!

Cozy & Quaint! The Little Cottage for Big Hearts.

The Faith Estate - A Lakefront Storybook House

Newly Renovated Cottage, Easy Walk to Downtown!

Remodeled 2/2 Baja style villa w/4 person cart
Family-friendly home rentals with a pool

The Silver Lake Estate

Quiet Neighborhood in the Country

Lake Sumter 2/2 Villa FREE gas cart/Pet friendly

Relaxing House in The Villages

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Location Can’t be Beat! With cart!

Magical Family Fun House Near Disney Luxury Villa

New Luxury Home-Pool-Waterfront View-3 King Suites
When is the best time to visit Leesburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$33,459 GYD | G$34,714 GYD | G$35,551 GYD | G$28,231 GYD | G$26,349 GYD | G$24,676 GYD | G$25,095 GYD | G$25,304 GYD | G$25,095 GYD | G$25,304 GYD | G$26,977 GYD | G$27,395 GYD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about vacation rentals that are family-friendly in Leesburg

Total vacation rentals
Explore 150 vacation rentals in Leesburg

Nightly prices starting at
Leesburg vacation rentals start at G$10,456 GYD per night before taxes and fees

Verified guest reviews
Over 3,190 verified reviews to help you choose

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
140 of Leesburg vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Leesburg rentals

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