Family-friendly holiday rentals in Leesburg

4.96 out of 5 average rating, 353 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.

4.99 out of 5 average rating, 145 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!

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!

4.96 out of 5 average rating, 144 reviews

4.98 out of 5 average rating, 439 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.

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.

4.97 out of 5 average rating, 107 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.

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.

FamilyIndoor spacesHospitality

4.95 out of 5 average rating, 227 reviews

A spacious wooden dock extends over the calm waters, surrounded by lush greenery. Several people are seated, enjoying a meal together. Lawn chairs are arranged comfortably, with trees reflecting off the clear surface of the water nearby, creating a serene atmosphere.

Home in Weirsdale

Beautiful House On the River, Kayaks, Large Dock!

Come relax by the river in this 3-bedroom, 2-bathroom vacation rental in Lady Lake, Florida. Recently built by our family in 2022, the home has a screened in back porch, a fire pit, WIFI, and is complete with a large private dock right on the Ocklawaha River. All that and it's located only 10 minutes from The Villages where you can shop and have fun. Centrally located 1-1/2 hours from Disney, Daytona beach, and Tampa. Lockbox key access is available for check-ins at any time of day.

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 close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

5.0 out of 5 average rating, 127 reviews

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.

4.9 out of 5 average rating, 192 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.

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, 160 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.

Indoor spacesHospitalityView

5.0 out of 5 average rating, 262 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.

Popular amenities for Leesburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 181 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

4.92 out of 5 average rating, 150 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

4.88 out of 5 average rating, 217 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

4.93 out of 5 average rating, 157 reviews

A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.

Home in Clermont

Spacious Bungalow with Pool and Courtyard

4.94 out of 5 average rating, 100 reviews

A vibrant bedroom is showcased with a tropical-themed quilt featuring large leaf patterns in teal and white. A decorative pillow with a starfish design is positioned on a spacious bed, complemented by a nightstand adorned with a small decorative palm tree.

Home in The Villages

3 BR 2 BA Coastal-vibe,Golf Cart,Pools, Pickleball

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

4.96 out of 5 average rating, 116 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

4.97 out of 5 average rating, 144 reviews

Home in Davenport

Magical 2 pool-Spa & Game Room Villa near “Disney”

Family- and pet-friendly home rentals

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

4.95 out of 5 average rating, 126 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

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

4.98 out of 5 average rating, 209 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

4.85 out of 5 average rating, 116 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

4.94 out of 5 average rating, 117 reviews

Townhouse in Mount Dora

The Art House/Fire Pit/Games/Sleeps 9/Near DT

4.97 out of 5 average rating, 115 reviews

Home in Mount Dora

Beautiful Mount Dora Charmer with Lake Ola Views

4.93 out of 5 average rating, 158 reviews

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

Red Bird Cottage and Farm: Equestrian lake cottage

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 276 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!

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

4.86 out of 5 average rating, 137 reviews

Home in Clermont

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

4.83 out of 5 average rating, 133 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!

4.92 out of 5 average rating, 53 reviews

Home in Fruitland Park

Luxury home with a pool and 3 bedroom

4.95 out of 5 average rating, 21 reviews

The Canal House on Lake Harris.

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