Holiday rentals in The Villages

4.94 out of 5 average rating, 142 reviews

Remodeled 2/2 Baja style villa w/4 person cart

4 person, yamaha gas golfcart offered at this baja style 1000 sqft 2BR, 2BA courtyard villa! It comes fully furnished with pots, pans, linens, and does have a blow dryer and keurig! located in the De La Vista South area just off Morse, this villa is just a short cart ride to Spanish Springs or Sumter Landing. The villa has new stainless appliances, beautiful plank flooring, and fresh paint. King bed in the master, queen bed in the guest bedroom. All bedrooms have smart TV's, cable in LR only

4.95 out of 5 average rating, 20 reviews

Cheerful King Bed Home in the Villages

Welcome to your perfect getaway in The Villages! This charming 2-bedroom, 2-bathroom home is ideally located for you to enjoy all the best amenities the area has to offer. Fenney Pitch and Putt is nearby, offering a fun and relaxing experience. The Sugar Cane Recreation Center, with its beautiful walking trail & adult pool is perfect for leisurely days under the sun. Also nearby is the popular Fenney Grill, with a resort style family pool, you can enjoy delicious meals and refreshing drinks.

4.96 out of 5 average rating, 163 reviews

Home away from home entire house

Located in an excellent area in the Chatham neighborhood, of the Bromley villas. This home offers easy access to restaurants, shopping and recreation. For nightly entertainment you're a short distance away from Lake Sumter land and Spanish Spring town Square where you will find many restaurants, grocery stores and free nightly live entertainment. This home is fully equipped with everything you need. Pets are allowed. Recreational guest passes included. Golf cart not included with reservation.

4.98 out of 5 average rating, 112 reviews

Private 2/2 Villa w/ New 4 Seat Gas Golf Cart

Relaxing home in quiet neighborhood w/ private yard, screened porch - rare in The Villages! Roanoke Retreat is a beautifully remodeled 2 bed/2 bath home - only 15 minute golf cart ride to Spanish Springs, 20 minutes to Sumter Landing . Rental includes 4 seat gas golf cart w/ access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in every room, fully equipped kitchen, new BBQ grill. 55+ community but no age restriction to visit

4.91 out of 5 average rating, 70 reviews

Villa la Bella

Stay in one of the most desirable locations in The Villages in the village of Sable Chase. Our beautifully remodeled and newly updated villa is just minutes from Sumter Landing in the heart of The Villages. Bright and airy feeling, tastefully designed and decorated, it features hardwood floors throughout. The 2BD, 2BA house with cozy lanai and new stainless gas grill also includes a Yamaha gas golf cart for your use. Your Villages vacation is ready for you at Villa la Bella!

4.99 out of 5 average rating, 116 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!

5 out of 5 average rating, 42 reviews

Villa in The Villages

Palm Oasis Retreat - Dog Friendly w/golf cart

Looking for a beautiful courtyard villa in a great location? Look no more! Conveniently located between Brownwood and Lake Sumter Landing, and close to Colony Plaza which includes grocery, gas, restaurants and more. This newly renovated villa is in the sought after Village of Charlotte. Located right in the middle of all the fun, this property is a short golf cart ride to the Charlotte Neighborhood pool, Captiva Recreation Center, shopping, and restaurants.

Superhost

4.86 out of 5 average rating, 122 reviews

Patio Villa, 5 mins from Sumter, FREE Gas Cart!

Adorable Patio Villa in a Prime Location. FREE GAS GOLF CART! Located in the heart of The Villages, in the village of Caroline. 5 minutes from Lake Sumter Landing, with bountiful options for golf, food, and entertainment just a short golf cart ride away. This isn’t your average, ‘bare bones’ investment rental. This is where our family stays when they come to visit. It is furnished with quality linens, furniture, kitchen equipment, Xfinity, & Roku.

4.9 out of 5 average rating, 42 reviews

Beautiful Designer Home -Golf Cart- Walk to Sumter

This stunning designer home comes with a golf cart and is within walking distance to Lake Sumter Market Square. It sleeps 4 adults in 2 bedrooms. 5G Wi-Fi. Kitchen is loaded with amenities & spices, lots of comfy lounging spaces, an inside laundry room, 2-car garage, landscaped yard and easy access to Hwy 466. 3-day min. May-Sep, 7-night min. Oct, Monthly stays only Nov-Apr. You will love staying in this stylish home away from home.

4.98 out of 5 average rating, 41 reviews

Great location w/ golf cart! Lake Sumter-Brownwood

This home greets you with a driveway Pelican painting, amazing landscaping and a decorative glass entry door. Savanna shutters and comfortable furniture throughout the home. 12 minute golf cart ride to Lake Sumter and 17 minutes to Brownwood Square. Use the included golf cart to get there! Sea Breeze Rec Center with pool, pickleball, etc. is just a few minutes away. Grocery stores closeby. Quiet neighorhood. Dogs under 25 lbs allowed.

4.95 out of 5 average rating, 126 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

4.96 out of 5 average rating, 103 reviews

Villa in The Villages

Villa 2 Master Suites/2 Golf Carts Great Location

Beautifully Remodeled Private Courtyard Villa with two King Master Suites. Both bedrooms come with King Posturepedic Pillow Top Mattresses and Premium bedding, each with their own private bathroom & 32" HDTV's. LOCATED PERFECTLY in the De La Vista North neighborhood between Spanish Springs & Sumter Landing both offering dinning and shopping. The property comes with 2 Golf Carts making getting around SUPER easy & FUN!

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Popular amenities for The Villages holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in The Villages

4.96 out of 5 average rating, 55 reviews

Beautiful Villages 2/2 Home. Perfect Location

ScottRating, 5 stars2 weeks ago

Thanks we are frequent visitors and stay was amazing! Would recommend!

4.96 out of 5 average rating, 26 reviews

Villanova - 2B/2B in The Villages with Golf Cart

JenniferRating, 5 stars3 weeks ago

We enjoyed our stay & the location was great for us as well. The home was perfect for our needs & we appreciated having a washer & dryer for our use. We would definitely stay again if needed in the future.

5 out of 5 average rating, 16 reviews

Perfect home-families/friends in The Villages, FL!

JohnRating, 5 stars6 months ago

Jeff and Aggie were excellent hosts and this is an outstanding house. My wife and I and our three adult children really enjoyed this house. The bedrooms and bathrooms are excellent, the kitchen and living area is large and outstanding and the pool/outdoor kitchen was impressive. This was a great experience, there were no issues or concerns at all. In addition, the communication was outstanding. Everything went very well.

5 out of 5 average rating, 11 reviews

TikiTiki walk/ride 2 Lake Sumter *Pool & Hot Tub*

MellisaRating, 5 stars5 days ago

By far the most well stocked Airbnb we’ve stayed in! Location was prime to everything, the hosts were very gracious and communicative as well. Adults and kids will have a blast in this house with so many games, activities and fabulous pool and hot tub area. Seriously could not ask for more in a great vacation rental!!

4.94 out of 5 average rating, 72 reviews

Golf Cart, King Bed, Small Dogs, and Water System!

AnnRating, 5 stars2 weeks ago

1000 words isnt enough . so warming and relaxing home. so much to do. book at least 10 days 7 is not enough . u will have memories that will draw you back. . This home exceeds any home i ever rented. around every bend on the golf cart paths you will find anouther bend of fun that goes on and on.... if u are craving a fast food for a quick bite to eat, where else can u go thru drive thru on a golf cart !

5 out of 5 average rating, 16 reviews

Private Villa by Lake Sumter Square

TerryRating, 5 stars1 month ago

I had a truly wonderful stay at Laura’s Airbnb this week! From the moment I arrived, Laura was incredibly helpful and welcoming. She’s not only a fantastic host but also a wealth of knowledge about the area—her recommendations made my trip even more enjoyable. The place itself was spotless, cozy, and full of charm. Every little detail showed care and thoughtfulness. Laura went above and beyond to make sure I felt comfortable and accommodated. I couldn’t have asked for a better experience. Highly recommend! If you're lucky enough to stay here, you're in for a treat. Five stars, two thumbs up.

4.94 out of 5 average rating, 86 reviews

Walk to Sumter w/cart - Beautiful Courtyard Villa

TinaRating, 5 stars2 weeks ago

Perfect, quiet and just like being at home! Loved getting a paper in the am, Nice touch! Great convenient area!