Family-friendly holiday rentals in The Villages

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, 150 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

5.0 out of 5 average rating, 8 reviews

Sunset Oasis - 3/2 w/ Pool & Golf Cart

Breathtaking! This 3BR 2BA w/ POOL and GOLF CART, in the Village of Lake Denham, will leave you speechless! Not only is paradise inside the house, but you have an amazing waterfront view while you revel in the private pool. Comfortable beds, open floor plan, it's stunning! Cruise around on the golf cart to discover rec. centers, pools, golf courses for all level of players, and pickleball courts. The squares certainly won't disappoint with their restaurants, shopping and nightly live music.

A screened-in patio features a refreshing private pool surrounded by lush landscaping. Two chaise lounges are positioned beside the water, while a float rests in the pool. A fountain adds a tranquil element to the relaxing outdoor space.

4.97 out of 5 average rating, 97 reviews

Casa Santin Luxury in The Villages w/Private Pool

A refined Florida Luxury home designed for effortless indoor-outdoor living, Casa Santin blends modern coastal style with relaxed comfort—creating the perfect escape for your next getaway. Your Private Oasis. The highlight of Casa Santin is the stunning screened lanai and private pool—your own resort-style sanctuary. Start your mornings with coffee in the sunshine, spend afternoons poolside, and unwind in the evenings with a western sunset, a glass of wine under the soft glow of the lanai.

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.

4.98 out of 5 average rating, 111 reviews

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.

4.85 out of 5 average rating, 130 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!

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.

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, 105 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.

A spacious living area is highlighted by a large, L-shaped sectional sofa with patterned pillows, surrounded by two blue armchairs. A round wooden coffee table sits centrally on a decorative rug, while natural light flows through windows that offer a view of the outdoors.

4.99 out of 5 average rating, 124 reviews

VIEW-T-FUL! w/Golf cart

Stunning entry with one of a kind picturesque setting and unbeatable location all in one. This lanai was redesigned with no support columns to have this spectacular highly desirable panoramic golf front & water view. Sweeping view of Southern charm, cluster of mature oak trees with Spanish moss. The back of the home facing the morning sunshine lighting up the lanai and screen area for a fine morning of relaxation. Don't hesitate, this home has it all, golf cart too!

4.96 out of 5 average rating, 100 reviews

King Bed, Golf Cart, Small Dogs & Water Filter!

Your NEW home includes a very comfortable KING BED and GOLF CART!! With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house NOVA WATER filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!! 2 SMALL DOGS OK.

An aerial view showcases a spacious property surrounded by lush greenery. The home features a neat driveway and is complemented by several nearby buildings, including a recreation center with a pool. Sunlight highlights the rooftops and well-maintained lawns.

5.0 out of 5 average rating, 108 reviews

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 four-seater golf cart is included. One minute to the Waterlily golf cart bridge and eight minutes to Brownwood Square. Or Edna’s on the Green is just a few minutes away.

4.99 out of 5 average rating, 173 reviews

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.

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, 155 reviews

Briar Meadow Villa - Dogs are welcome!

Dogs are welcome in this nicely furnished Courtyard Villa, with a fenced in backyard. Near Nancy Lopez Legacy Golf & Country Club, Mulberry Grove Rec Center, dog park, Publix, Walgreens, & The Club Health & Rehab Clinic. Easy access to pools, golf courses, dining, shopping & the squares at Spanish Springs & Sumter Landing. Includes gas Golf Cart*, Comcast cable TV, high speed WIFI, & Villages Daily Sun. *Subject to availability

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, 157 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

Popular amenities for The Villages family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.92 out of 5 average rating, 146 reviews

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

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.

4.83 out of 5 average rating, 246 reviews

A charming treehouse sits elevated among large trees, connected by a wooden bridge. Surrounding space features a well-arranged outdoor sitting area with round wooden seating, and ample green grass is visible below, enhancing the natural setting.

Treehouse in Ocala

Woodpecker Treehouse Retreat

4.88 out of 5 average rating, 214 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

4.92 out of 5 average rating, 146 reviews

Cottage in Clermont

Private Country House | 16 Guests | Gatherings

4.98 out of 5 average rating, 177 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

4.95 out of 5 average rating, 103 reviews

Apartment in Ocala

Dreamy Studio in The Heart of Horse Country

A spacious home is showcased amidst lush landscaping, featuring multiple palm trees and colorful shrubs. The exterior highlights a warm yellow facade with a welcoming front porch. A clear blue sky with scattered clouds adds to the inviting atmosphere of the property.

4.76 out of 5 average rating, 37 reviews

The Grandview

Family- and pet-friendly home rentals

5.0 out of 5 average rating, 251 reviews

Guesthouse in Lady Lake

Cute & Cozy Tiny Guesthouse

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, 189 reviews

Home away from home entire house

4.96 out of 5 average rating, 351 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

5.0 out of 5 average rating, 18 reviews

Eastport Emerald Escape 2BR Luxury in Well Point

A heated pool is enclosed within a screened patio, featuring gentle water features and surrounded by lush greenery. Two wooden adirondack chairs and a small side table are positioned nearby, inviting relaxation in this outdoor space.

5.0 out of 5 average rating, 19 reviews

The Villages | Heated Pool | Walk to Sawgrass!

5.0 out of 5 average rating, 13 reviews

The Creative Cottage! Premium Amenities!

5.0 out of 5 average rating, 13 reviews

Home in Lady Lake

House on Golf Course, with Heated Pool & Golf Cart

Superhost

5.0 out of 5 average rating, 4 reviews

Heated Pool + GOLF CART - Village of Santiago!

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 72 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

5.0 out of 5 average rating, 10 reviews

Home in Wildwood

Stylish Villages Getaway

5.0 out of 5 average rating, 11 reviews

The Palm Pool House!

5.0 out of 5 average rating, 43 reviews

The Palms. Luxurious, giant pool, golf, pond view

4.91 out of 5 average rating, 96 reviews

A private heated pool is framed by a spacious lanai with a sleek, white deck. The pool features a shimmering blue surface and tiled border. Surrounding walls provide privacy while natural light pours in from above, creating a bright and inviting space.

Home in Wildwood

New, private pool getaway in The Villages, FL

The exterior of a newly constructed home features a light color palette with a modern design. A spacious driveway leads to a three-car garage, flanked by neatly trimmed greenery and a landscaped yard under a clear blue sky.

4.97 out of 5 average rating, 71 reviews

The Villages-3 bd (3 king)/3 full ba+Cart NEW HOME

4.9 out of 5 average rating, 10 reviews

Living the Dream | Pools, Golf & Entertainment

A decorative entrance sign for Villa De La Vista South is set against lush greenery and vibrant flowering plants. The sign stands prominently atop a circular flower bed, with a clear blue sky and soft clouds in the background.