Family-friendly vacation rentals in The Villages

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.

The Villages Retreat- Free Coffee, Brand New!

Welcome to The Villages Retreat, a charming house nestled in the heart of Moultrie Creek Village! This delightful property boasts three bedrooms, providing ample space for a comfortable stay, perfect for families or groups visiting to watch their grandkids sports games, or to celebrate their graduation! This Home is Centrally Located and is within 5 minutes from locations such as: The Villages Charter Highschool and it's stadiums, The Tracy Performing Arts Center, and East Port Town Square.

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!

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.

Marsh Bend Waterview Oasis in The Villages

Picture yourself staying at our Sanctuary overlooking the peaceful water view in the Village of Marsh Bend. Take a short stroll across the street to Edna's Beer & Wine Garden or enjoy the nearby pool or Pitch N Putt. This beautiful, ultra clean, new home can be your next oasis and you enjoy preparing a meal in the beautiful kitchen with all of the necessities. 3 Bedrooms and 2 Bathrooms give you plenty of room to enjoy the house for yourselves or have a few guests.

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.

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!

Welcome to The Sanctuary~Pet Friendly w/Golf Cart

Enjoy a stylish experience at this brand new, centrally located upscale home we call The Sanctuary! Enjoy a brand-new spacious home with stylish furniture, comfortable beds, and an excellent location. Equipped with bikes, a golf cart and portable chairs for those nights at the square enjoying live entertainment, what more could you want? PLEASE NOTE: We require a signed rental agreement and a copy of your ID to finalize your reservation.

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

Begonia on the Bend – Stylish Home Near Sawgrass

🌴 Modern 3BR/2BA Begonia-style home in The Villages’ new Cason Hammock neighborhood. Built in 2021, this spacious 2,083 sq ft retreat features an open layout, oversized garage + golf cart garage, and stylish comfort throughout. Walk to Sawgrass Town Square, McGrady’s Pub, pool, rec center, and Fresh Market. Enjoy The Villages lifestyle with everything you need for a relaxing stay!

3/2 Courtyard Villa in The Village of Citrus Grove

Get comfortable and enjoy plenty of extra room at this spacious home. Large courtyard with a patio and lanai to soak in the Florida weather, open & spacious floor plan, TVs in both living room and master bedroom, and more! Only minutes away from Ezell recreation center and Homestead recreation center; close to pickleball, pools, classes, golfing, etc.