Holiday rentals in Lake Sumter

Getaway on the Waterway: Kayak, SUP, fish, relax!

Welcome to your peaceful Getaway on the Waterway right on the beautiful canal that connects Big and Little Lake Weir! Kick your feet up and wave at the boats going by as you grill or fish from the dock. Play a round of corn hole, hop on one of our paddleboards or kayaks for beautiful ride to either lake! Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, (they also offer sunset cruises and water taxi service to Eaton's Beach restaurant right from our dock!) RELAX and ENJOY!

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.

Heated Pool Golf Cart Dog Friendly in The Villages

Nestled amidst lush greenery and shrubs ,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. The flow between indoor and outdoor spaces offers an ideal retreat. Conveniently located, Vida Rosa is just a short golf cart ride away from the squares of Spanish Springs and Lake Sumter offering a variety of restaurants, shopping, and entertainment.

Charming Villages Retreat

Charming 2B/2B Cottage Villa near Sumter Landing and Spanish Springs Escape to this beautifully updated villa in The Villages. Enjoy a designer kitchen, cozy living room with sectional and 75” TV, and French doors leading to a screened lanai. The private, fenced courtyard is perfect for relaxing under party lights. The master suite includes a walk-in closet and blackout shades. Explore with the included golf cart, access 50 golf courses, 100+ pickleball courts, pools, and nightly entertainment.

Sumter Landing Oasis / Golf Cart

Enjoy a stylish experience at this centrally-located courtyard villa. Walking distance to Lake Sumter Landing Town Square, grocery stores, shops and restaurants. This home is perfectly located to access golf courses, recreational centers, pickleball courts, and the town square. You can hear the music being played at the town square from the backyard! 2 seat gas golf cart is included. Practice your putting on your private putting green! There is a minimum 3 month rental for stays from Jan-March.

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.

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

Virginia Trace | 1 mile to square, walk to pool

1 mile from Lake Sumter Town Square Virginia Trace Villa has everything you need in this updated 3 BR, 2 bath 1740 sq ft villa. A perfect space centrally located to explore The Villages. The villa features a spacious LR area w/ a 65" smart TV, fully stocked kitchen, 2 dining areas, & screened in patio where guests can relax & enjoy the sitting area. In unit washer & dryer. Wifi & parking included. Golf cart accessible. Guest passes available upon request (provide info 3 days prior to check-in).

1198 Merryweather; 3BR at Lake Sumter just 2nt min

Large 3BR/2BA courtyard villa. Affordable luxury & 5-star reviews. PRIME LOCATION in CENTER of community. Upscale furnishings. Short walk to central town square w/shops & restaurants. King, queen, full beds all with newer quilts sleep 6 comfortably. Fast WIFI, 2 brand new Samsung Smart TVs (65" living room); 2 desks for laptop/at-home work. Private yard. Newer patio chairs. Vinyl plank floor. I also manage 2br home across street. Rent both to sleep 10; Rest of 2025=2nt min. Pet ok (w/fee).

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.

Cozy A-Frame Retreat w/ hot tub!

Escape to our cozy A-frame cabin, nestled amidst the serene beauty of nature. Just 10 mins from Santos Trailhead and 35 from Rainbow Springs! After a day of exploration, unwind in the private hot tub, gather around the bonfire pit for s'mores, or snuggle by the fireplace and stream your favorite movie. Whether you seek a romantic retreat or an extended family getaway, our A-frame cabin promises the perfect blend of nature's tranquility and modern comfort!

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