Family-friendly vacation rentals in Lady Lake

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.

FamilyKitchenOutdoor spaces

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.

Indoor spacesKitchenBackyard

4.99 out of 5 average rating, 143 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!

KitchenIndoor spacesDecor

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, 161 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 spacesFamilyCleanliness

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.

FamilyKitchenGetting around

5 out of 5 average rating, 6 reviews

Villa in Lady Lake

Private Patio | Pickleball | Pool | Golf | WiFi

Welcome to your sun-filled villa in The Villages, Lady Lake—a beautifully updated retreat designed for comfort and relaxation. The bright open floor plan features a fully equipped kitchen, inviting living space, and plenty of natural light throughout. Step outside to your private patio, perfect for morning coffee or peaceful evenings. Walk to Spanish Springs for live music, dining and shopping, plus enjoy resort-style amenities including pools, pickleball, tennis, and golf. Free parking.

DecorNearbyComfort

4.96 out of 5 average rating, 223 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 spacesKitchenSleep quality

Superhost

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

4.85 out of 5 average rating, 131 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.

FamilyKitchenDecor

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 spacesComfort

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 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.

FamilyKitchenAmenities

5 out of 5 average rating, 259 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.

KitchenFamilyHiking

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.

4.96 out of 5 average rating, 158 reviews

Villages-Private Heated Pool-Central Location

Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

Indoor spacesFamilyComfort

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

4.95 out of 5 average rating, 105 reviews

Apartment in Ocala

Dreamy Studio in The Heart of Horse Country

Indoor spacesKitchenLong stay

A single-story home with a light beige exterior is set against a clear blue sky. Lush palm trees and manicured landscaping surround the entrance, which features a paver driveway leading to a double-garage door. The overall setting reflects a serene neighborhood ambiance.

5 out of 5 average rating, 26 reviews

On The Links-4bd w/pool in Spanish Springs!

Indoor spacesFamilyNearby

4.98 out of 5 average rating, 101 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!

KitchenFamilyTV

Superhost

A serene lakeside view is presented, featuring calm waters reflecting a gradient of soft colors during sunset. A wooden dock extends into the water, framed by lush greenery and grasses. The landscape conveys a tranquil setting, inviting moments of reflection in nature.

Home in Winter Garden

4.94 out of 5 average rating, 142 reviews

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

Indoor spacesKitchenCleanliness

4.98 out of 5 average rating, 177 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

Indoor spacesFamilyWifi

Superhost

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

4.85 out of 5 average rating, 100 reviews

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

Indoor spacesKitchenBathroom

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 out of 5 average rating, 127 reviews

Safari themed private addition with pool/hot tub.

FamilyIndoor spacesPets

4.97 out of 5 average rating, 107 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

Indoor spacesKitchenHot tub

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 87 reviews

A wooden deck surrounds the home, featuring seating areas with two vibrant chairs and a table centered around a fire pit. An umbrella provides shade for outdoor lounging. The exterior of the house displays a light beige siding with a door and window that allow natural light in.

Home in Weirsdale

Cheerful, two bedroom Animal loving home,

FamilyKitchenQuiet

4.93 out of 5 average rating, 153 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

KitchenFamilyAmenities

4.97 out of 5 average rating, 106 reviews

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.

Home in Leesburg

Waterfront cottage Haynes Creek

KitchenIndoor spacesDecor

Place to stay in Mount Dora

The exterior of the waterfront residence is illuminated with colorful string lights, creating a festive ambiance. A spacious patio area is visible, featuring a dining table and seating. Large glass windows allow for views of the living space inside, enhancing the open-air feel.

4.98 out of 5 average rating, 290 reviews

The Boat House on Lake Dora - Downtown Waterfront

Indoor spacesKitchenBathroom

4.97 out of 5 average rating, 76 reviews

The Promise Land~10 beds~New

Indoor spacesKitchenLocation

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, 113 reviews

FREE Golf Cart + Fabulous Location + Classy Decor!

Indoor spacesKitchenLocation

A screened lanai features comfortable seating and is positioned adjacent to a well-maintained backyard. A tree is situated in the grassy area, providing shade, while a concrete pathway leads to the entrance. A white fence encloses the yard, enhancing privacy.

4.92 out of 5 average rating, 157 reviews

Briar Meadow Villa - Dogs are welcome!

Indoor spacesKitchenNearby

4.96 out of 5 average rating, 136 reviews

A rustic bedroom features a uniquely designed wooden bed with natural log accents and decorative pillows. Complementary wall art and hanging plants create a cozy atmosphere. Light streams in through horizontal blinds, adding warmth to the natural wood and brick elements of the room.

Cabin in Ocklawaha

Countryside Loft at Coco Ranch

FamilyIndoor spacesCheck-in

Family-friendly home rentals with a pool

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

FamilyKitchenGetting around

The open living area showcases a cozy red sofa facing a large TV mounted on the wall. A sleek kitchen bar with three red stools is situated nearby, and a chair with a patterned design complements the modern decor. Natural light is visible from an entrance.

4.9 out of 5 average rating, 73 reviews

The Villages, De La Vista West 1762

KitchenFamilyWifi

4.99 out of 5 average rating, 73 reviews

The exterior of the villa is showcased, featuring a well-maintained facade with a garage and a driveway. Lush palm trees and neatly trimmed bushes contribute to the inviting landscape, while a white privacy wall offers additional seclusion. The dynamic sky adds a vibrant backdrop.

Villa in The Villages

Perfect location Lake Sumpter Villa w/ Golf Cart

KitchenFamilyAccuracy

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, 73 reviews

KingBed w/Cart

FamilyKitchenSleep quality

5 out of 5 average rating, 28 reviews

The private pool area is enclosed by a screened lanai, illuminated by string lights. A relaxing area features loungers beside the pool, with a raised spa and gentle water feature. Lush greenery surrounds the space, creating a serene atmosphere.

Villa in Lady Lake

Heated Pool Golf Cart Dog Friendly in The Villages

KitchenFamilyComfort

4.98 out of 5 average rating, 47 reviews

A spacious property is presented, featuring a two-story cottage with blue accents and a gravel driveway leading to the entrance. A screened-in pool area is visible on the left, surrounded by greenery and mature trees. The overall setting is tranquil and inviting.

Home in Marion County

Cozy Pool Cottage by Lake Weir

Indoor spacesKitchenTV

5 out of 5 average rating, 12 reviews

Home in Weirsdale

Hilltop Hideaway Lake Weir

FamilyKitchenBeach