Holiday houses in The Villages

A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.

4.96 out of 5 average rating, 134 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, 324 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.

A modern home with a welcoming facade features a dual garage and a front entrance illuminated by a stylish light fixture. Large windows reflect the evening light, while a manicured lawn with minimal landscaping is visible in the foreground.

5 out of 5 average rating, 25 reviews

3/2 Designer Home W/ Golf Cart

Make this home your Villager get away! This is a designer home fully furnished with everything you will need for your vacation. This home is perfectly located minutes away from Sawgrass where you can enjoy live music every night. 🎶 The home is only an 18 minute drive from Brownwood which is a crowd favorite town-center. Home comes with a 4 seater golf cart perfect for adventuring to the pickleball courts, golf courses, pools & so much more! Come enjoy the sunshine in the beautiful Villages😀

A well-maintained home is visible, with a neatly landscaped driveway leading to a garage. An orange golf cart is parked prominently in front, surrounded by lush green grass and a manicured shrub nearby. A white picket fence adds charm to the yard.

4.98 out of 5 average rating, 120 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

A single-story home features a simple façade with a covered entryway and a spacious driveway. Lush green grass borders the driveway, complemented by small landscaping elements. The neighborhood displays well-maintained properties on either side, under a clear blue sky.

4.96 out of 5 average rating, 57 reviews

The Sunshine Retreat with Golf Car

Come and enjoy this beautiful 2 Bed/2 Bath Patio Villa Home. We have made it very relaxing and welcoming for your stay. You will enjoy just a 3 minute golf car ride to Sawgrass, 15 minute golf car ride to new Eastport and a 20 min ride to Brownwood. It’s only a 5 minute walk to the pool and Aviary rec center is about a 5 minute golf car ride away. Golf Car included with home. Renter assumes all liability and will be responsible for any damage or injury caused by the use of the golf car.

An outdoor view of the home's exterior is presented, featuring a silver golf cart parked on a concrete driveway. The well-maintained front yard includes a white picket fence and landscaped areas with shrubs. A spacious garage is visible in the background under a clear blue sky.

4.91 out of 5 average rating, 57 reviews

Stunning Villa 2B/2B With Golf Cart

Make this stunning home your retirement Villager get away! Located in the Village of Newell home is minutes away from Sawgrass, swimming pools, pickleball, golf, and so much more. This home comes with a 2 seater golf cart and an outdoor grill perfect for any season. Live music is a nightly occurrence and only a 5 minute golf cart ride away. Enjoy the sunshine with biking and walking paths only seconds away from the front door! We would love to host your next Villages, FL vacation!

An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.

4.99 out of 5 average rating, 82 reviews

New Luxury Home-Pool-Waterfront View-3 King Suites

Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

Place to stay in The Villages

An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.

5 out of 5 average rating, 97 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!

4.84 out of 5 average rating, 103 reviews

An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.

Villa in The Villages

Location Can’t be Beat! With cart!

Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

A spacious living area is highlighted by a large, L-shaped sectional sofa with patterned pillows, surrounded by two blue armchairs. A round wooden coffee table sits centrally on a decorative rug, while natural light flows through windows that offer a view of the outdoors.

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, 47 reviews

The exterior of a villa is showcased at dusk, featuring a well-maintained landscape with palm trees and shrubs. A two-car driveway leads to a garage, with soft lighting illuminating the entrance. The sky reflects pink and purple hues overhead.

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.

The exterior of the home displays a well-manicured front yard with decorative plants and a white picket fence. A paved driveway leads to a two-car garage featuring a symmetrical design, accompanied by a clear blue sky above.

4.95 out of 5 average rating, 87 reviews

King Bed, Small Dogs OK, and 4-Seater Golf Cart!

Your NEW home includes a very comfortable KING BED. 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!!

Popular amenities for The Villages holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in The Villages

A spacious living area is presented, featuring a light-colored sofa paired with white accent tables. A ceiling fan above enhances airflow, and modern kitchen appliances are visible in the background. Natural light floods the space, highlighting the hardwood flooring and simple decorative touches.

5 out of 5 average rating, 18 reviews

Bay Breeze Villa

4.95 out of 5 average rating, 21 reviews

Spotless Villa Near Brownwood Sq- Lanai & King Ste

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, 96 reviews

Fabulous Courtyard Villa close to Sumter Landing

5 out of 5 average rating, 24 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

4.94 out of 5 average rating, 16 reviews

Outdoor Fun at the Pool + 2 Golf Carts!

The exterior of a single-story home is showcased, featuring a well-maintained front yard with greens and flowering shrubs. A paved driveway leads to a two-car garage, while the entrance is framed by neat landscaping. The sky above is clear and bright.

4.94 out of 5 average rating, 17 reviews

The Villages, Citrus Grove home away from home

4.96 out of 5 average rating, 80 reviews

A golf cart in a vibrant green color is parked outside a garage with a door adorned by multiple windows. The home features beige siding, and a lush green lawn is visible, complemented by a white picket fence in the background.

Villa in The Villages

Melody Lane's Crafting Getaway - Cricut Included

The exterior of the villa features a charming design with a white picket fence surrounding well-maintained landscaping. Lush green grass and neatly trimmed shrubs complement the palm trees, while a clear blue sky provides a bright backdrop.