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Family-friendly holiday 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.

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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 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.
Guest house 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

Guest favourite
A well-lit bedroom features a spacious bed made with white linens, complemented by bedside tables and lamps. Two chairs are positioned alongside the bed. Art depicting landscapes hangs above the bed, while light filters through a window adorned with white blinds and red curtains.
Flat in Belleview
4.92 out of 5 average rating, 150 reviews

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.

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
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.
Guest house in Deer Island
4.95 out of 5 average rating, 128 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.

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 small lakefront house with a neatly manicured front yard is visible, featuring a covered porch and a low fence. The entrance is framed by two square windows on either side of the door, and trees provide a backdrop in the distance.
Home in Eustis
4.88 out of 5 average rating, 145 reviews

House on Lake Eustis

Located in Eustis Florida. Next to the Lake Eustis Sailing Club, Small Lakefront house with 1 bedroom, 1 bathroom, Living Room, Full Kitchen, Small desk for working, Screened Porch with beautiful lake views. Close to restaurants, grocery stores, and parks. 10 minutes from Mount Dora, one hour from both the East and West coasts. One hour from Disney World and most attractions. 4.2 Miles or 10 minutes from Advent Health Waterman NOTE: NO ANIMALS OF ANY KIND ARE ALLOWED DUE TO ALLERGIES!

Top guest favourite
A gentle-looking fox rests on the ground beneath a fence, surrounded by greenery. Its white fur blends with the natural surroundings, and its dark eyes reflect curiosity. The area is covered with soft earth and decorative wood chips, creating a tranquil setting.
Farm stay in Dade City
4.93 out of 5 average rating, 347 reviews

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

Guest favourite
A cozy sleeping area is highlighted by two queen-size beds, each adorned with checkered yellow and white blankets. A lamp on a nightstand provides gentle illumination, and natural light filters through the window, which is fitted with blinds.
Guest house in Mount Dora
4.96 out of 5 average rating, 261 reviews

Cozy Buttercup Cottage!

Cozy 1/1 cottage- independent building, + nice breakfast kitchen, dining, & living room, great screened porch. 4 minute drive from Renninger’s, 5 minutes from Mount Dora City Hall Area where you'll find unique shops, restaurants, antiques, art museums, galleries, marina, parks, & many activities! *32 min/ Universal Studios & Island of Adventure, 43/ Magic Kingdom, 40 min/ Orlando Intl. Airport, 36 min/ Sanford-Orl Airport, 18 min/ Rock Spring, 48 min/ Silver Glenn Spring & much more!

Top guest favourite
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.
Guest house in Tavares
4.98 out of 5 average rating, 128 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!

Popular amenities for Leesburg family-friendly rentals

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Quick stats about holiday rentals that are family-friendly in Leesburg

  • Total holiday rentals

    Explore 150 holiday rentals in Leesburg

  • Nightly prices starting at

    Leesburg holiday rentals start at £38 per night before taxes and fees

  • Verified guest reviews

    Over 3,190 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    140 of Leesburg holiday rentals include wifi 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!