Holiday rentals in The Villages

Sunny Sky's Paradise w/Golf Cart

Experience unparalleled relaxation at our stunning new patio villa. This beautifully designed home features an open floor plan, a spacious two-car garage, a screened-in porch, and an outdoor patio. Enjoy the vibrant lifestyle of The Villages with endless activities—all just a golf cart ride away. Our villa is equipped with everything you need: bikes, a golf cart, high-speed internet, smart TVs, and more. Conveniently located near top attractions like Orlando, Disney World, and numerous beaches.

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.

Bay Breeze Villa

Welcome to Bay Breeze Villa, where modern comfort meets coastal charm. This brand-new 2-bedroom, 2-bath patio villa seamlessly blends style and functionality with sleek finishes and an inviting atmosphere perfect for relaxing or entertaining. Located in a vibrant community, close to top-rated restaurants, beautiful golf courses, and nightly entertainment. Embrace the relaxed yet active lifestyle you’ve been dreaming of – Bay Breeze Villa is the perfect place to call your home away from home.

Sunnyside Escape in The Villages | Golfcart | BBQ

With a two-seater golf cart included, you’re just minutes from Brownwood Paddock, 3 pools (only 4 mins away), Publix, Aldi, & Winn-Dixie, all within 5 mins. This home has everything you need for a comfy stay! Enjoy your stay with a BBQ, a comfy patio, or hop on the stationary bike if you’d like to workout. Both bedrooms have styled ensuite bathrooms, each furnished with a queen bed & TV. Please be advised that there's a $50 charge to get the lifestyle IDs & a $20 golfcart insurance fee.

Margaritaville-3/2 w/ Pool & Golf Cart Included

Welcome to Margaritaville! This 3 BR, 2 BA house with a POOL and large lanai is awaiting your stay! The BRs are beachy with 1 king and 2 queens. The open kitchen, dining and living area has a 75" tv - great for relaxing, but the real gem is enjoying the lanai with plenty of seating, a grill, firepit, and a beautiful pool with wall so you are completely secluded from people and surrounded by lush plants. Then hop in the golf cart to enjoy music at any of the nearby squares. Pure Luxury!

Heated Pool Golf Cart Dog Friendly in The Villages

Nestled amidst lush greenery ,Vida Rosa’s private pool provides a serene outdoor oasis, complete with a dining area, loungers, and a gas BBQ. The luxurious accommodations are thoughtfully designed to evoke a sense of calm and elegance. Conveniently located, just a short golf cart ride away from the squares of Spanish Springs & Lake Sumter offering a variety of entertainment etc. Note: The pool has a jet tub attached to it. The water temperature is the same temperature as the pool, 86 .

Luxury Villages Stay • Golf Cart • Near Brownwood

Welcome to your Villages retreat! Step into comfort and style in this beautifully decorated, designer home fully furnished with everything you need for a relaxing stay. From cozy bedding to modern furniture. Located in the sought-after Village of Osceola Hills, end of Moyer Blvd just south of Route 44, this spacious 3-bedroom, 3-bathroom home (2021 sq. ft.) features a 2-car garage and comes with a golf cart. You're just minutes away from Brownwood (3 miles) and Sawgrass Grove (2 miles).

Convenient Home in The Villages

This Quiet Home comes with all of the amenities of the villages, including Golfing, Pickleball Courts, Bocce Ball, Shuffleboard, Billiards, Community Pools (heated to 85 degrees) (card needed - ask for details) The Lenai area is ideal for relaxing with nature. The home backs onto a walking/bike trail (no golf carts or other vehicles). Open Concept with 2 Work Desks. Fast 1G wifi Parking for 1 in the Garage. Washer/Dryer, DW, 4 Smart TVs with video streaming apps and Roku TV live.

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 patio villa in Deluna, The Villages w/ Golf Cart

Enjoy this beautiful 2/2 home in De Luna. With quick access to the turnpike and I-75 to enjoy everything in and around the Villages. This Ruby model villa is close to Brownwood and Ednas’ on the Green & soon to be East Port. It comfortably fit 4 people in two queen beds. The living room can fit two on the pull out sectional. The front screen porch is a wonderful place to wave to your neighbors while you have your morning coffee or just the place to relax before going to bed.

Private Villa + Golf Car by Lake Sumter Square

Welcome to our cozy 3-bedroom, 2-bath courtyard villa in the Village of Virginia Trace, just 4 minutes from Lake Sumter Square. Enjoy the convenience of nearby shopping, dining, and entertainment. The private, fenced yard with a fire pit and grill is perfect for outdoor living. The rental includes an electric atomic golf cart for easy exploring. Inside, the villa is bright and comfortable, with a king bed in the primary room and queen beds in the other two.

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.