Vacation rentals with a pool in The Villages

4.95 out of 5 average rating, 124 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

4.96 out of 5 average rating, 310 reviews

Home in Lady Lake

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.

5 out of 5 average rating, 14 reviews

Entire Home with an Office in Fenney

My home is furnished for the ultimate in guest comfort and working online. Accommodates maximum of 2 guests who plan to sleep in the same bed. Only 1 bed provided. Bright office with large desk, printer, TV Furnishings are modern & luxurious, making you feel right at home. Fast Internet & YouTube TV Fully stocked kitchen Coffee & tea is complimentary Filtered home water system Please NON-smokers ONLY welcome NO pets Not suited for children Fees reduced for 28+ days, ask for details

5 out of 5 average rating, 19 reviews

Pirates & Parrots - The Villages - w/Golf Car !

GREAT LOCATION!! A beautiful 2 bedroom 2 bath home with a heated saltwater pool and a hot tub. 77 inch TV with sound system, and 2 car garage/golf cart . Outdoor bar with big screen TV with seating area and a second seating area outside the bird cage. TV’s in both bedrooms. Great out door living! Minutes to everything via golf car: Brownwood 12 Sumter 16 Sawgrass 19. 4 champ golf and 7 exec golf courses 5-10. Publix, Walmart 5 minutes Golf Car 2020 Yamaha included! No smoking!!

4.93 out of 5 average rating, 132 reviews

Pool, golf cart, private backyard. Paradise!

Come and enjoy this relaxing piece of paradise surrounded by lush greenery with your own, small, private pool (not heated). "Serene on the Green" is a beautifully remodeled 3 bedroom, 2 bathroom designer home (1,536 sqft) with a large screened outdoor pool area with lots of privacy. Our location 320 steps from the Santiago Recreation Complex with two golf courses and a short ride to Lake Sumter Landing and Spanish Springs is perfect. A new custom 2021 Yamaha QuieTech golf cart is included!

5 out of 5 average rating, 15 reviews

Heated Pool, Dog Friendly, Golf Cart Included

Welcome to your dream getaway! Our exquisite 2 bed, 2 bathroom home is a true haven of luxury and relaxation. From the moment you step through the front door, you'll be enveloped in an atmosphere of opulence. Indulge in a restful night's sleep in our meticulous bedrooms, each adorned with plush bedding and upscale furnishings. The sparkling pool beckons for refreshing swims, while the adjacent hot tub provides the perfect spot for soaking under the stars. Don't forget the games room.

Place to stay in The Villages

5 out of 5 average rating, 93 reviews

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!

4.91 out of 5 average rating, 66 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!

5 out of 5 average rating, 11 reviews

Incredi-Bill Jo's

Get ready for an incredible stay at our Incredi-Bill Jo's stylish and cozy pool home. You'll be steps away from world class shopping, dining, entertainment, sports, recreation and GOLF. This three bedroom home is close to all of the amenities that make The Villages the number one destination for active adults year after year. And to make your stay even more incredible, you'll have the convenience and use of a beautiful golf cart! Come and see what all the fuss is about!

4.94 out of 5 average rating, 70 reviews

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

Your NEW home includes a very comfortable KING BED, complimentary GOLF CART, and golf clubs. With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house 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!!

4.99 out of 5 average rating, 139 reviews

Whole House 3 Bedroom (sleeps 10) in The Villages

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.