Family-friendly holiday rentals in The Villages

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.

Pool and fun right out back

Bring the family to this beautiful place with lots of room for fun. With the Waterlily Rec Center right out back you can walk to the family pool in just a few steps. Pickle ball, exercise equipment, corn hole, bocce ball, shuffleboard and a walking/biking path is all right out the back door. A golf cart is included for golfing and access to the rest of The Villages. 1 minute to the Waterlily golf cart bridge and 8 minutes to Brownwood Square. Or Edna’s on the Green is just a few minutes away.

Across pool, golf cart, modernized, private

Spend your summer - whatever time of the year it may be - at Summer on the Hill, our freshly remodeled vacation home in the village of Summerhill. Summer on the Hill combines the conveniences of home with the tropical atmosphere of a Florida oasis. On a large lot, surrounded by majestic oak trees with a private lanai and screened front porch across the street from the neighborhood adult pool there is no better place to relax. Golf cart included. Spend your summer ANYTIME at Summer on the Hill!

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.

Robin's Song in Brownwood

WELCOME to the beautiful ROBIN's SONG conveniently located in The Village of Atwood where you are just minutes from all the fun and activities in The Villages. Just a 2 minute ride on the Yamaha GOLF CART (extra charge) into the famous BROWNWOOD PADDOCK SQUARE where you will enjoying shopping, dinning and live music each evening from 5 to 9 p.m. Just a minute ride to THE GRAND TRAVERSE PLAZA housing Publix, or the relaxing Brownwood Hotel and Day spa featuring the Wolfgang Puck Restaurant.

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

Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. Golf cart included in price for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

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.

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.

Private 3/2, 2 Golf Carts, Pizza Oven, Game Table!

3-bedroom (sleeps 6), 2-bath home in The Villages with 2 golf carts! Screened & covered patio includes grill, pizza oven, fire table, outdoor seating, table and privacy - rare in The Villages! Access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in family room, all bedrooms & patio, fully equipped kitchen, gaming table & more! 10 minutes to Spanish Springs & Sumter Landing Town Squares.

Get it all - Pool, Jacuzzi, Golf View, & Golf Cart

Book your next Villages vacation with Everything! Sparkling pool with Jacuzzi and 4 person golf cart. Fantastic Golf views because it's located right on Hole #1 of Tierra Del Sol Champonship Golf Course. It includes a well stocked kitchen, coffee bar, office space with desk, Large Screen Smart TV's, BBQ grill, and a wonderful shaded patio. Close to everything! 2.3 miles to Spanish Springs Town Square, and 3.2 miles to Lake Sumter Landing.

Brewed Awakening-3/2 w/ Private Pool and Golf Cart

The heart of this home lies in its resort-style patio, a true outdoor sanctuary designed for ultimate enjoyment. The expansive patio area boasts a shimmering, shapely pool, inviting you to take a refreshing dip on warm summer days. Entertain with ease in the spacious outdoor living area. Whether you're hosting a poolside soirée or enjoying a quiet evening, the patio offers unparalleled versatility for all your entertainment needs.

Fenney Waterview Retreat w/Pool in The Villages

If you are looking for a Tranquil escape, then this is the right home for you. Sit by the pool and overlook the sun dance upon the sparkling water as you sip on your drink or read a great book. This Ultra Clean 3 bed/3 bath home has all of the comforts you'll be looking for. There's plenty of space for you and friends or family as everyone has their own space in the home.