Family-friendly vacation rentals in Lady Lake

A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.

4.95 out of 5 average rating, 154 reviews

2/2 custom pool home with 4 person gas golf cart

Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

FamilyKitchenCondition

4.98 out of 5 average rating, 126 reviews

3/2 w/ Two Golf Carts (6 seats), ~1 mile Sumter

Remodeled 3 bed (sleeps 6), 2 bath home in The Villages, only ~1 mile to Sumter Square! Screened patio backs up to 6 acre lot, very private except the cows! Rental includes access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Free use of 2 gas golf carts (4 +2 seats) to get to it all! Newly furnished home includes 5 smart TV's, including on patio, fully equipped kitchen, BBQ grill and more. Bedrooms include 1 king, 1 queen and 2 full beds.

Indoor spacesKitchenAmenities

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.

4.96 out of 5 average rating, 352 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.

KitchenFamilyTV

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!

KitchenFamilyGetting around

A single-story home is situated on a corner lot, surrounded by well-maintained lawns and landscaping. Large trees provide shade, while the blue sky creates a bright backdrop. A screened-in porch and patio area are visible on the side of the house.

4.98 out of 5 average rating, 162 reviews

Whole House-sleeps 10 The Villages Spanish Springs

Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

Indoor spacesFamilyGrill

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

Best sunset on Lake Weir! Lake front with private sand beach we are located on Sunset Harbor on Lake Weir. Plenty of dock space and beach space for several boats. House is on Bird Island and setup for entertaining friends and family. House was completely remodeled in 2018 with a modern contemporary design featuring 4 bedrooms, 2 bathrooms. One of the rooms is a movie theater with a 100” big screen that has a futon sofa. Can take the boat to Eaton’s Beach or Gator Joes just across the lake!

Indoor spacesFamilyGrill

A single-story home is showcased with a light exterior and an attached two-car garage. Neat landscaping featuring low-maintenance gravel and diverse shrubs surrounds the entrance. A clear blue sky and a few palm trees contribute to the inviting atmosphere of the property.

4.89 out of 5 average rating, 115 reviews

Walk to Sumter w/cart - Beautiful Courtyard Villa

We love this home because the location is FANTASTIC! It's under a mile to Sumter Landing (walking distance for us :)). Also, new floors, paint, etc! The living room furniture is extremely comfortable! The kitchen has everything you need. The beds are comfortable and there is a tv in every room. (The second bedroom but needs your own Roku or Firestick!) There is a cart included which is the best way to see The Villages. We know you will love it here! Let us know if you have any questions.

KitchenFamilyBathroom

4.96 out of 5 average rating, 225 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.

Indoor spacesFamilyBeach

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.

4.83 out of 5 average rating, 133 reviews

Location Can’t be Beat! With cart!

Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

FamilyKitchenLaundry

The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.

4.97 out of 5 average rating, 106 reviews

Fabulous Courtyard Villa close to Sumter Landing

This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

KitchenFamilyPets

A comfortable living area features a light-colored sectional sofa and a textured rug. A wall-mounted television is positioned above an elegant gray console table adorned with small potted plants. Soft lighting is provided by pendant lamps, complemented by natural light from a nearby window.

4.95 out of 5 average rating, 88 reviews

Villages, FL. Designer Home 2 blocks from town SQ!

Location!Location! Location! Designer home with access to close shopping,pools, tennis, golf, pickle ball, live bands every night, and it’s all within 5 minutes on golf cart! High speed Wifi. Grocery stores are 2 blocks from house! Golf cart is included with house. The house is located one hour north of Orlando, and 1 hour and 9 minutes away from Disney World! There is so much to do here in The Villages you can find something of interest for everyone in the family! Enjoy!

FamilyIndoor spacesSleep quality

The modern home features a spacious driveway leading to a large carport and a two-car garage. A covered porch with steps provides access to the front entrance, surrounded by greenery and trees.

5.0 out of 5 average rating, 66 reviews

Villages home with unique elevated front porch

A bright 2 bed, 2 bath home with new flooring throughout, includes golf cart. Located in historic Country Club Hills. Less than two miles from Spanish Springs Square with restaurants, shops & FREE nightly entertainment. Minutes away from pools, hot tubs, recreation centers, walking paths, & golf courses. Fully equipped kitchen with starter pack. Relax with a book & a drink on the breezy front porch with an overhead fan. Free Netflix, Peacock Premium & high speed internet.

FamilyKitchenParking

Popular amenities for Lady Lake family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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

KitchenFamilyParks

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.

5.0 out of 5 average rating, 127 reviews

Safari themed private addition with pool/hot tub.

FamilyIndoor spacesAccuracy

4.81 out of 5 average rating, 259 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 spacesQuiet

4.93 out of 5 average rating, 147 reviews

Cottage in Clermont

Private Country House | 16 Guests | Gatherings

Indoor spacesKitchenHot tub

4.98 out of 5 average rating, 102 reviews

The pool area is illuminated at night with vibrant lights, casting colorful reflections on the water. The curved shape of the pool is complemented by a spa and surrounded by lush greenery. A safety fence surrounds the space, enhancing privacy.

Home in Lecanto

Serene Paradise Heated Pool/HotTub/TikiBar 4 BR's

Indoor spacesFamilyGetting around

4.99 out of 5 average rating, 174 reviews

Farm stay in Pierson

Ruby Oaks Farm w/ Beach Near St. JohnsRiver

FamilyIndoor spacesQuiet

4.98 out of 5 average rating, 103 reviews

An outdoor space features a heated swimming pool beside a lanai. A table with chairs and a television is situated under the screened roof, while a hot tub is positioned nearby. Two inflatable rings float in the clear water, surrounded by potted plants.

Home in Citrus Springs

Private Spa *Heated Pool* & Firepit Near Manatees!

KitchenFamilyAmenities

4.97 out of 5 average rating, 108 reviews

A spacious outdoor area features a large pool with crystal-clear water, accompanied by a hot tub and a soothing water fountain. Surrounding the pool, a stone patio hosts multiple seating areas beneath a pergola, providing a serene setting for relaxation.

Home in Orlando

Unique Spacious Home w/ Pool near Downtown Orlando

FamilyIndoor spacesGrill

Family- and pet-friendly home rentals

A spacious living area features a large teal sectional sofa accented with decorative pillows. In the center, a round coffee table displays a floral design. Abundant natural light floods the room through wide windows, enhancing its relaxed atmosphere.

4.95 out of 5 average rating, 111 reviews

3/2 Luxury Villa, Golf cart included! Near Sumter!

KitchenFamilyWalkability

A single-story home is depicted in a well-kept neighborhood, featuring a manicured lawn with palm trees and shrubs. Two vehicles, including a golf cart, are parked in the driveway, while a cloudy blue sky provides a serene backdrop.

4.96 out of 5 average rating, 120 reviews

FREE Golf Cart + Fabulous Location + Classy Decor!

Indoor spacesKitchenAccuracy

A single-story home showcases a light-colored exterior and a welcoming front porch, bordered by a white picket fence. Neatly trimmed shrubs and grass surround the home, adding to the cheerful curb appeal. A paved driveway leads to a garage on the right.

4.96 out of 5 average rating, 192 reviews

Home away from home entire house

KitchenFamilyPool

Two golf carts are parked on the driveway of a villa, one black and one red. Lush greenery, including palm trees, enhances the front yard, which is well-maintained and features a blend of grass and decorative plants. A clear blue sky and sunshine create a bright atmosphere.

4.97 out of 5 average rating, 119 reviews

Villa 2 Master Suites/2 Golf Carts Great Location

KitchenFamilyNearby

5.0 out of 5 average rating, 13 reviews

House on Golf Course, with Heated Pool & Golf Cart

Indoor spacesFamilyLong stay

The exterior of a cottage is displayed, featuring a paved driveway leading to a two-car garage. A large tree provides shade, surrounded by well-maintained grass and landscaping. The home showcases a welcoming entrance with a decorative star, under a clear blue sky.

5.0 out of 5 average rating, 34 reviews

Spanish Springs/The Villages/Orlando Home

Indoor spacesFamilyPool

4.96 out of 5 average rating, 27 reviews

An open living space features a high wooden ceiling with stylish light fixtures. A dark leather sofa sits across from a small dining table set for two. Nearby, a compact kitchen area contains essential appliances and storage, enhancing the functionality of the cozy apartment.

Apartment in Lady Lake

Desperado 1 - Cozy Peaceful Apt in Lady Lake, Fl.

Indoor spacesFamilyCleanliness

4.89 out of 5 average rating, 37 reviews

Charming and relaxing home

KitchenFamilySleep quality

Family-friendly home rentals with a pool

The image captures a welcoming street view of a residential area with charming homes featuring varied architectural styles. Lush palm trees and neatly trimmed shrubs outline the landscaped front yards. The sky is bright with fluffy clouds, contributing to the overall inviting atmosphere.

4.94 out of 5 average rating, 101 reviews

1199 Merryweather - Walk to Lake Sumter Landing Sq

Indoor spacesKitchenBiking

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.

4.86 out of 5 average rating, 276 reviews

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

FamilyKitchenHospitality

4.98 out of 5 average rating, 59 reviews

Relaxing House in The Villages

FamilyIndoor spacesAccuracy

The exterior of a single-story home is shown, featuring a light-colored façade with multiple windows. A landscaped front yard includes a manicured lawn and decorative stones. A two-car garage with a driveway is visible on the right side. Palm trees are present in the surrounding area.

4.9 out of 5 average rating, 49 reviews

Beautiful Designer Home in The Villages Fl

KitchenFamilyComfort

5.0 out of 5 average rating, 8 reviews

Villa in Lady Lake

Private Patio | Pickleball | Pool | Golf | WiFi

LocationComfortHospitality

A green golf cart is parked on a stone driveway in front of a light-colored house. The cart features a canopy and seating for four, with two spacious seats in the front. The garage door is seen in the background, providing additional context of the home.

4.92 out of 5 average rating, 74 reviews

KingBed w/Cart

KitchenFamilyAccess

5.0 out of 5 average rating, 5 reviews

Heated Pool + GOLF CART - Village of Santiago!

HospitalityAccuracyCleanliness

A welcoming facade of a single-story home is presented, featuring a combination of red brick and light-colored siding. An American flag is displayed at the entrance. Lush green grass surrounds the walkway, leading to a covered porch and large windows that allow natural light to brighten the interior.