Holiday rentals in The Villages

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Top-rated holiday rentals in The Villages

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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.
Home in The Villages
4.96 out of 5 average rating, 141 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

Top guest favourite
The exterior of a modern villa is depicted, showcasing a light-coloured facade with a two-car garage. A white picket fence encircles manicured shrubs and grass. The front porch is partially visible, with large windows inviting natural light.
Home in The Villages
5 out of 5 average rating, 17 reviews

Blue Sky Villa, Your Home Away From Home.

Your enjoyment is our ultimate goal and the Blue Sky Villa Team goes the extra mile to deliver on our promise. From the tranquility of the Master Bedroom to the Master Bathroom with its spa-like shower heads with unlimited filtered hot water, to the open format Kitchen that is stocked with quality appliances and so many extras, to the on-site Laundry Area; your hosts at Blue Sky Villa are focused on your peace and comfort. There's even complimentary unlimited use of a Golf Cart and two bikes.

Superhost
Home in The Villages
5 out of 5 average rating, 3 reviews

Pool House Near Eastport and Middleton

Relax at this peaceful new home in The Villages. Only minutes to Eastport Sawgrass and Middleton. Enjoy the beautiful outdoor area and heated pool (heated for additional $20/day) with plenty of space and seating. There are TVs in the living bedrooms and the lanai to watch from the pool or comfortable outdoor seating. There’s a king bed in the master and queens in each of the guest bedrooms. Your stay includes a gas 4 seater Yamaha golf cart and probably a 2nd cart. That one’s not promised.

Guest favourite
Home in The Villages
5 out of 5 average rating, 5 reviews

Sunset Oasis - 3/2 w/ Pool & Golf Cart

Breathtaking! This 3BR 2BA w/ POOL and GOLF CART, in the Village of Lake Denham, will leave you speechless! Not only is paradise inside the house, but you have an amazing waterfront view while you revel in the private pool. Comfortable beds, open floor plan, it's stunning! Cruise around on the golf cart to discover rec. centers, pools, golf courses for all level of players, and pickleball courts. The squares certainly won't disappoint with their restaurants, shopping and nightly live music.

Guest favourite
The private pool area is enclosed by a screened lanai, illuminated by string lights. A relaxing area features loungers beside the pool, with a raised spa and gentle water feature. Lush greenery surrounds the space, creating a serene atmosphere.
Villa in Lady Lake
5 out of 5 average rating, 24 reviews

Heated Pool Golf Cart Dog Friendly in The Villages

Nestled amidst lush greenery ,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. Conveniently located, just a short golf cart ride away from the squares of Spanish Springs & Lake Sumter offering a variety of entertainment etc. Note: The pool has a jet tub attached to it. The water temperature is the same temperature as the pool, 86 .

Guest favourite
Home in The Villages
5 out of 5 average rating, 12 reviews

Luxury Villages Stay • Golf Cart • Near Brownwood

Welcome to your Villages retreat! Step into comfort and style in this beautifully decorated, designer home fully furnished with everything you need for a relaxing stay. From cozy bedding to modern furniture. Located in the sought-after Village of Osceola Hills, end of Moyer Blvd just south of Route 44, this spacious 3-bedroom, 3-bathroom home (2021 sq. ft.) features a 2-car garage and comes with a golf cart. You're just minutes away from Brownwood (3 miles) and Sawgrass Grove (2 miles).

Top guest favourite
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.
Home in The Villages
4.98 out of 5 average rating, 101 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.

Top guest favourite
A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.
Home in The Villages
5 out of 5 average rating, 46 reviews

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

GREAT LOCATION!! A beautiful 2 bedroom 2 bath home with a 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 2022 Yamaha included! No smoking!!

Top guest favourite
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.
Home in The Villages
4.97 out of 5 average rating, 103 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.

Superhost
Home in The Villages
5 out of 5 average rating, 5 reviews

Luxury Pool Home with a View in The Villages, FL

Enjoy your own private sports pool, spa, and climate-controlled lanai as well as all of the amenities that The Villages has to offer. Free executive golf courses, water volleyball, and water aerobics for stays of 30+ days. Pickleball, tennis, billiards, shuffleboard, bocce ball, outdoor exercise equipment and nightly entertainment for all guests. Get to Brownwood town square in approximately 10 minutes. This home is located on a pond with a natural preserve beyond the pond.

Top guest favourite
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.
Home in The Villages
5 out of 5 average rating, 39 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.

Top guest favourite
Home in The Villages
4.99 out of 5 average rating, 165 reviews

Private 3/2, 2 Golf Carts, Pizza Oven, Game Table!

3-bedroom (sleeps 6), 2-bath home in The Villages with 2 golf carts! Screened & covered patio includes grill, pizza oven, fire table, outdoor seating, table and privacy - rare in The Villages! Access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in family room, all bedrooms & patio, fully equipped kitchen, gaming table & more! 10 minutes to Spanish Springs & Sumter Landing Town Squares.

Popular amenities for The Villages holiday rentals

When is the best time to visit The Villages?

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Avg. price£119£130£124£96£85£81£76£74£78£85£97£105
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • What are the best places to stay in The Villages?

    Many travelers choose vacation rentals around Spanish Springs, Lake Sumter Landing, or Brownwood, as these areas bring together local dining, entertainment, and scenic spots. Each neighborhood has unique personality and access to golf courses or walking paths.

  • What are the best things to do in The Villages with kids?

    Families often explore community recreation centers, playgrounds, and pools, or attend outdoor music events and markets. Miniature golf and nature preserves are also frequently suggested for a fun family outing.

  • What are some of the best things to do in The Villages?

    Explore the lively town squares—Spanish Springs, Lake Sumter Landing, and Brownwood—for shopping, live music, and local dining. Recreational trails, championship golf courses, and arts centers bring added variety.

  • How is the weather in The Villages?

    The Villages has mild winters around 49–72°F (10–22°C), with warmer, humid summers that reach 92°F (33°C). Rainfall is most frequent in summer, so lightweight layers and rain gear can help you stay comfortable.

  • What are the best places to visit in The Villages?

    Many visitors explore Spanish Springs Town Square, Lake Sumter Landing, and Brownwood Paddock Square for nightly live music, open-air markets, and local shops. Community nature preserves and recreation centers add options for outdoor experiences.

  • What are some hiking trails in The Villages?

    Scenic paths in community nature preserves and walking trails near Lake Sumter Landing are often suggested for gentle strolls. Many neighborhoods have paved and shaded routes suited for a leisurely walk.

  • What are some family activities we can do in The Villages?

    Families can enjoy pools, community recreation centers, weekly outdoor music in the town squares, and local farmers markets. Mini-golf and arts workshops are also popular choices for a shared outing.

  • What are some of the best day trip ideas from The Villages?

    Day trips around The Villages often include nature parks, state forests, or visiting historic downtowns in surrounding towns. Springs, wildlife preserves, and local art districts provide further options for exploring the region.

  • Are there any pet friendly accommodations available in The Villages?

    Various vacation rentals in The Villages welcome pets, particularly in neighborhoods with access to walking trails and green spaces. Nearby parks often provide space for pets to stretch their legs.

  • What are some local tips for visiting The Villages?

    Many guests find it helpful to explore the town squares by golf cart to experience local life. Community clubs frequently welcome newcomers for recreation, and casual attire is comfortable for most outings.

  • What is The Villages known for?

    The Villages is known for its vibrant town squares, active recreation scene—including golf, pickleball, and social clubs—and nightly live music events. Designed as a community hub, it brings together seasonal residents and visitors for local experiences.

  • What are the best hidden gems to explore in The Villages?

    Many enjoy small community gardens, independent art galleries, and backstreet local cafes tucked between the main squares. Less crowded neighborhood pools and walking paths offer a quieter pace.

  • What are the best foods to try in The Villages?

    The Villages has a range of Southern-inspired comfort food, fresh seafood dishes, and classic American favorites. Around town squares, guests often discover local restaurants with regional flavors and specialties.

  • What should I bring for a trip to The Villages?

    Pack lightweight, breathable clothing for warm weather, comfortable walking shoes, a reusable water bottle, and a hat or sun protection. If visiting in summer, an umbrella or rain jacket is useful for frequent showers.

  • What is the nightlife in The Villages like?

    Nightlife in The Villages centers on the lively town squares, where outdoor music performances, line dancing, and gathering spots are common. Visitors often explore casual pubs, wine bars, and evening social events.

  • What are the most popular events or festivals in The Villages?

    Seasonal festivals, such as holiday parades and craft fairs around the town squares, are frequently suggested. Outdoor concerts, classic car shows, and market nights are also popular throughout the year.

  • Are there family friendly vacation rentals in The Villages?

    Family-friendly vacation rentals are available throughout The Villages, especially near recreation centers and walking paths. Many offer access to community pools, playgrounds, and outdoor gathering spaces.

  • When is the best time to visit The Villages?

    Late fall through early spring is often recommended for milder temperatures and comfortable outdoor weather. Summer tends to be hotter and more humid, with frequent rainfall.

Quick stats about holiday rentals in The Villages

  • Total holiday rentals

    Explore 850 holiday rentals in The Villages

  • Nightly prices starting at

    The Villages holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 16,890 verified reviews to help you choose

  • Family-friendly holiday rentals

    790 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 350 rentals that welcome pets

  • Holiday rentals with a pool

    340 properties feature pools

  • Rentals with dedicated workspaces

    550 properties have a dedicated workspace

  • Wifi availability

    850 of The Villages holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Pet-friendly and Laptop-friendly workspace across The Villages rentals

  • 4.9 Average rating

    The Villages stays are highly rated by guests – averaging 4.9 out of 5!

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  2. United States
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  5. The Villages