Family-friendly vacation rentals in Leesburg

4.96 out of 5 average rating, 355 reviews

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

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.

Indoor spacesKitchenCheck-in

Place to stay in The Villages

An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.

Safari themed private addition with pool/hot tub.

This special Guest house addition is Central to everything in The Villages! Making it easy to plan your visit. In The Village of Osceola Hills @ Soaring Eagle Preserve. Just North of Rt 44. A short golf cart or car ride to Brownwood Square & Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Play over 50 golf courses at a minimal fee, & free rec centers! We have an easy 4 seater Golf-cart rental , & request free Guest passes!

FamilyKitchenQuiet

5.0 out of 5 average rating, 128 reviews

4.99 out of 5 average rating, 146 reviews

A scenic view of a tranquil canal is presented, bordered by lush greenery. A wooden dock extends into the water, accommodating a boat. Nearby, comfortable outdoor seating is available, surrounded by natural landscaping, offering a peaceful outdoor space.

Home in Summerfield

Getaway on the Waterway- Dock+Kayaks+SUP board

Welcome to your peaceful Getaway on the Water. Whether you or your group are visiting the Villages, or just need a peaceful getaway to recharge, this is the place!There's something for everyone! Paddleboard or Kayak (provided) the beautiful canal to either lake. Enjoy your morning coffee or evening cocktail in nature on the dock. Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, they also offer sunset cruises and water taxi to Eaton's Beach restaurant right from our dock!

Indoor spacesKitchenGrill

Guesthouse in Deer Island

Sapphire Cottage - sleeps 6, on 5 acres with canal

Escape to Sapphire Cottage, a 5-acre wooded retreat with a private canal boat dock. Relax by the shared pool, fish from the dock, or enjoy a BBQ at the firepit. Our cozy cottage features a queen master, 2 sofa-beds, a full kitchen, and dining for 6. From meeting our farm animals, biking, kayaking, or reading in the gazebo, there is something for everyone! We live in the main house across the way and are happy to help while ensuring you have a peaceful stay. Come make lasting memories with us!

KitchenFamilyBathroom

4.96 out of 5 average rating, 145 reviews

4.98 out of 5 average rating, 441 reviews

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

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 food 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.

FamilyIndoor spacesHospitality

A charming cottage is nestled among lush greenery and palm trees. A concrete pathway leads to the entrance, flanked by vibrant plants in pots. Stairs ascend to the front door, inviting guests to explore the cozy interior.

4.95 out of 5 average rating, 109 reviews

Waterfront cottage Haynes Creek

Enjoy all central Florida has to offer, at this cozy waterfront cottage, on Haynes Creek, part of the Harris Chain. Fish from the dock, or bring your own watercraft, you have your own boat slip. Explore the area on our paddleboat, kayaks or paddle board. If its shopping and nightlife you enjoy we are close to Leesburg, Eustis, Mt. Dora, Tavares and the Villages. Or maybe you would enjoy watching wildlife and exploring one of the many parks or trails in the area. Central Florida has it all.

KitchenIndoor spacesQuiet

4.98 out of 5 average rating, 115 reviews

An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.

Home in The Villages

New Luxury Home-Pool-Waterfront View-3 King Suites

Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

KitchenFamilyCleanliness

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.

4.89 out of 5 average rating, 181 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.

KitchenIndoor spacesView

4.9 out of 5 average rating, 193 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.

Indoor spacesFamilyCheck-in

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.

4.98 out of 5 average rating, 163 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.

KitchenIndoor spacesQuiet

4.95 out of 5 average rating, 129 reviews

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

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!

Indoor spacesFamilyWalkability

5.0 out of 5 average rating, 265 reviews

Guesthouse in Lady Lake

Cute & Cozy Tiny Guesthouse

Take it easy at this cozy and peaceful getaway located in a safe and quiet neighborhood near The Villages. It's conveniently located all within 1.5 miles to Walmart, Aldi, Waffle House, McDonald's, Pizza Hut, Cracker Barrel, BJ's Wholesale and many other shops and restaurants. Plus, The Villages Hospital. We are also located two miles from The Villages Spanish Springs town square which has free entertainment from 5pm to 9pm every night of the week.

Indoor spacesFamilySolo travel

Popular amenities for Leesburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 153 reviews

The exterior of a spacious single-story house is visible, featuring a light-colored facade and a greenery-laden yard. A palm tree is seen in the foreground, while the driveway leads towards a garage on the right side.

Home in The Villages

Entire 3 BR Home(Sleeps 8)+Hot Tub in The Villages

KitchenIndoor spacesLaundry

4.94 out of 5 average rating, 162 reviews

An enclosed patio features a heated saltwater pool, accentuated by stone tile and decorative mosaic. Nearby seating options are visible, including a lounge chair under a shaded canopy. Lush greenery surrounds the area, providing a sense of privacy and tranquility.

Home in The Villages

Villages-Private Heated Pool-Central Location

KitchenFamilyCondition

4.88 out of 5 average rating, 218 reviews

A modern living space is illuminated by soft sunlight streaming through large windows. The wooden flooring creates a warm ambiance, while a sleek sectional couch and decorative partition subtly define the area. A potted plant adds a touch of greenery to the environment.

Home in Summerfield

Modern Lake Weir House

FamilyIndoor spacesNearby

4.98 out of 5 average rating, 183 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

Indoor spacesFamilySleep quality

4.85 out of 5 average rating, 101 reviews

A custom home is framed by lush greenery and mature trees. The landscaped yard features a manicured lawn, and the house showcases a welcoming façade with multiple windows, allowing natural light to enhance its inviting presence.

Home in Summerfield

A+ Privacy | Hot Tub | BBQ + Dining | Family +Pets

FamilyIndoor spacesGrill

4.82 out of 5 average rating, 266 reviews

A treehouse elevates above the ground, surrounded by lush greenery and lit by soft string lights. A cozy fire pit area with wooden seating is positioned beneath the treehouse, inviting gatherings in a natural setting. The space emphasizes tranquility and connection with nature.

Treehouse in Ocala

Woodpecker Treehouse Retreat

KitchenIndoor spacesSleep quality

4.96 out of 5 average rating, 118 reviews

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

KitchenIndoor spacesCheckout

4.94 out of 5 average rating, 142 reviews

A colorful bunk bed structure is featured, decorated in vibrant shades of yellow, blue, and orange. The mural backdrop depicts a jungle scene with a leopard and tropical plants, enhancing the playful atmosphere of the room. Spiral staircases offer access to the upper sleeping area.

Townhouse in Davenport

WaterPark+Arcade+KingBed+Hot Tub+NearDisney

Indoor spacesFamilyValue

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 101 reviews

3 Bed, 2 Bath, Waterfront, Dock, Large Driveway

KitchenIndoor spacesParks

The welcoming entrance of the home features a bright yellow façade with white trim and a covered porch. Two rocking chairs are situated on the porch, and brick steps lead up to the front door, framed by simple white columns.

4.97 out of 5 average rating, 202 reviews

Country Chic Cottage with Private Boat Parking

KitchenFamilyHospitality

4.97 out of 5 average rating, 116 reviews

Home in Mount Dora

Beautiful Mount Dora Charmer with Lake Ola Views

KitchenFamilyPets

4.85 out of 5 average rating, 117 reviews

A modern living area features a spacious sectional sofa in gray, complemented by a wooden coffee table. The open floor plan connects to a kitchen with stainless steel appliances and seating for four at the bar. Decorative wall elements add interest to the neutral walls.

Home in Lake Panasoffkee

Heated Pool & Kayaking House in Lake Panasoffkee

KitchenFamilyLaundry

An open living area features a stylish blue sofa and a mustard-yellow couch, accompanied by a round coffee table. A dining set with teal chairs and a kitchen bar area are visible. Natural light enters through windows, highlighting the warm wood flooring.

4.77 out of 5 average rating, 140 reviews

Retreat with/full kitch/near pavilion/fenceyrd

KitchenIndoor spacesAccuracy

4.98 out of 5 average rating, 210 reviews

A well-appointed sleeping area features a white bed frame with plush bedding in navy and white tones. Two bedside tables with navy blue lamps flank the bed. Decorative pillows, including a map-themed cushion, add interest, while framed botanical prints hang above the headboard.

Cottage in Mount Dora

Charming Mount Dora Cottage • Walk to Downtown

FamilyIndoor spacesWifi

A spacious saltwater pool is enclosed by a screened area, surrounded by lush greenery and landscaping. Lounge chairs and a small jacuzzi can be seen along the poolside, with sunlight reflecting off the water's surface.

4.91 out of 5 average rating, 81 reviews

Entire private home/heatedpool/boat or rv parking

FamilyKitchenPets

A single-story home is set against a clear blue sky, featuring a well-maintained driveway and a landscaped yard. Palm trees and shrubs surround the property, providing a refreshing backdrop. The house displays a contemporary design with a mix of light and dark exterior colors.

4.91 out of 5 average rating, 86 reviews

Tranquil Central FL Retreat

FamilyKitchenValue

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 160 reviews

A serene pool area is enclosed by a mesh screen, featuring clear blue water and a decorative fountain. A stone statue adorns the poolside, alongside a woven basket filled with towels. Lush greenery and a calm lake are visible in the background.

Home in Wildwood

Fenney Waterview Retreat w/Pool in The Villages

FamilyKitchenQuiet

4.86 out of 5 average rating, 277 reviews

An elegantly appointed dining area is highlighted by a dark table surrounded by gray upholstered chairs. Two candles sit atop the table, with a decorative bowl in the center. Soft lights hang overhead, illuminating the blue walls adorned with framed art and decorative shelves.

Villa in The Villages

Perfect "get-away" home for a couple or family!

FamilyKitchenSleep quality

4.86 out of 5 average rating, 137 reviews

Home in Clermont

Mario-Themed Home! | Disney 30 Min | Pool + Lake

KitchenFamilyOutdoor spaces

4.84 out of 5 average rating, 134 reviews

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

Location Can’t be Beat! With cart!

FamilyKitchenAccuracy

4.92 out of 5 average rating, 53 reviews

Home in Fruitland Park

Luxury home with a pool and 3 bedroom

KitchenFamilyLaundry

The exterior of a contemporary two-story home is highlighted, featuring large windows that provide natural light to the interior. A private pool is visible in the foreground, surrounded by lounge chairs and a dining area, with a clear blue sky offering a serene backdrop.

4.91 out of 5 average rating, 32 reviews

Boat Friendly & Private Pool Near The Villages

KitchenFamilyView

4.82 out of 5 average rating, 17 reviews

Rustic Modern Retreat w/ Private Pool – Leesburg

KitchenFamilyHospitality