Holiday rentals in Lake Sumter

A decorative entrance sign for Villa De La Vista South is set against lush greenery and vibrant flowering plants. The sign stands prominently atop a circular flower bed, with a clear blue sky and soft clouds in the background.

4.94 out of 5 average rating, 17 reviews

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.

5 out of 5 average rating, 23 reviews

An open living space features a cozy sleeping area and a small dining arrangement. Wooden beams highlight the ceiling above. Natural light enters through the door and windows, while a television and kitchenette with appliances are visible against the walls.

Flat in Lady Lake

Desperado 2 - Cozy Peaceful Apt. Lady Lake FL.

Escape to your unique and private 2nd story apartment nestled on 2 acres of serene land and just a short 7-minute drive to The Villages. Enjoy the tranquility of nature while still being close to vibrant entertainment, shopping and dining options. Your cozy and well appointed space offers the perfect blend of seclusion and convenience making it an ideal getaway for relaxation and rejuvenation. *perfect for vacation *perfect for traveling workers *perfect for visiting family in the The Villages

4.96 out of 5 average rating, 331 reviews

A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.

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.

The exterior of a single-story villa is depicted, featuring a light-colored stucco facade and a two-car garage. Paved driveway curves towards the entrance, with decorative landscaping including a potted plant and stone accents. Windows are adorned with decorative arches, enhancing curb appeal.

4.95 out of 5 average rating, 158 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

The image captures a welcoming street view of a residential area with charming homes featuring varied architectural styles. Lush palm trees and neatly trimmed shrubs outline the landscaped front yards. The sky is bright with fluffy clouds, contributing to the overall inviting atmosphere.

4.94 out of 5 average rating, 99 reviews

1199 Merryweather - Walk to Lake Sumter Landing Sq

Wow! Gorgeous 2br/2ba courtyard villa; 5-star reviews. Walk to Creekside Landing pool & town square in THE most sought after location in the community. Private yard. Granite counters, vaulted ceilings, big birdcage, French doors & vinyl plank floor. No carpet. Newer recliners, patio chairs, and sofa. King in master. Queen in guest br. Cable. WIFI. Rent a golf cart (optional). No pets here. I manage a pet friendly 3br across street (sleeps 6). Apr & Dec 2026=5nt min. Other 2026=just 2nt min.

4.95 out of 5 average rating, 38 reviews

An open-concept living space is visible, featuring a kitchen island with a speckled countertop. A dining table with several chairs is positioned nearby, while a comfortable seating area showcases a large TV, lighting, and decorative plants, contributing to a welcoming environment.

Villa in The Villages

Location! Charming, Premium Courtyard Villa

LOCATION!!! This charming private, end of the block, courtyard villa is a very short walk to Sumter Landing. Walk to Caroline Community Pool and Rec Center. Near Mallory Hill Golf Course and Country Club. New to the rental market, this villa is pristine!! High end finishings throughout. Spacious open floor with 3 private bedroooms, 2 bathrooms, Lanai and Private Backyard. **Golf cart use is available for reservations that are 7 days or more. Golf cart use is subject to approval of host.

5 out of 5 average rating, 5 reviews

Entire 1BR home- The Villages- Spanish Springs

Beautifully decorated villa! Enjoy a stylish experience at this 1 BR Villa located 5 minutes from all of the fun at Spanish Springs Square. (Restaurants, Entertainment and more.) Property is off Morse Blvd which makes it convenient to Lake-Sumter Landing Square as well. You can enjoy a nice show at the Sharon Performing Arts Center or @ The Studio Theater and have fun at the Squares all in one stay! Promo-Guests that stay 28 days or more, will receive a $50 credit for the amenities fee.

The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.

4.97 out of 5 average rating, 102 reviews

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.

4.96 out of 5 average rating, 114 reviews

Two golf carts are parked on the driveway of a villa, one black and one red. Lush greenery, including palm trees, enhances the front yard, which is well-maintained and features a blend of grass and decorative plants. A clear blue sky and sunshine create a bright atmosphere.

Villa in The Villages

Villa 2 Master Suites/2 Golf Carts Great Location

DUE TO CANCELLATION FEB & 1/2 MAR AVAILABLE! 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!

A screened-in patio area showcases two hanging chairs with cozy cushioning, accompanied by a low coffee table. A lush green artificial lawn enhances the space, while a ceiling fan provides airflow. Beyond the screens, outdoor seating is visible under a shaded canopy.

5 out of 5 average rating, 38 reviews

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.

4.96 out of 5 average rating, 232 reviews

The A-frame cabin features a striking black exterior with large windows that reflect the surrounding greenery. A spacious wooden deck is highlighted, equipped with a picnic table. Lush trees frame the cabin, creating a serene and inviting outdoor setting.

Cabin in Ocala

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!

The exterior of the home showcases a well-manicured lawn with vibrant landscaping. Palm trees and shrubs frame the entrance, while a driveway leads to the two-car garage. The home features a charming façade, complemented by a clear blue sky above.