Holiday houses in The Villages
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Top-rated holiday rentals in The Villages
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Patio Villa Near BrownWood
Enjoy your beautiful Colony Patio Villa in PINELLAS. Near Brownwood Town Square, Eisenhower regional rec center, & Bonifay and Evan’s Prairie CCs. WALKING DISTANCE to Big Cypress, 3 executive courses, and PINELLAS PLAZA (with Winn Dixie, restaurants & more) January to March bookings must be for a full calendar month (beginning and ending on the 1st and last, respectively) The Villages is an Active 55+ Community. Young visitors are allowed for limited periods with plenty of family activities.
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.
Home away from home entire house
Located in an excellent area in the Chatham neighborhood, of the Bromley villas. This home offers easy access to restaurants, shopping and recreation. For nightly entertainment you're a short distance away from Lake Sumter land and Spanish Spring town Square where you will find many restaurants, grocery stores and free nightly live entertainment. This home is fully equipped with everything you need. Pets are allowed. Recreational guest passes included. Golf cart not included with reservation.
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
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!
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.
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!
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.
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!
Peaceful Farm Cottage Near Villages | Garden, Pets
Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.
Beautiful Designer Home -Golf Cart- Walk to Sumter
This stunning designer home comes with a golf cart and is within walking distance to Lake Sumter Market Square. It sleeps 4 adults in 2 bedrooms. 5G Wi-Fi. Kitchen is loaded with amenities & spices, lots of comfy lounging spaces, an inside laundry room, 2-car garage, landscaped yard and easy access to Hwy 466. 3-day min. May-Sep, 7-night min. Oct, Monthly stays only Nov-Apr. You will love staying in this stylish home away from home.
The Villages Oasis
Welcome to The Villages Oasis! This charming villa offers a relaxing getaway with its private pool and hot tub. Enjoy comfortable accommodations with two bedrooms, a fully equipped kitchen, and convenient amenities like air conditioning and Wi-Fi. Located on Morse Road just a 5 minute drive from Spanish Springs, you'll have easy access, shopping, and more. Enjoy the perfect blend of relaxation and recreation in this beautiful Florida retreat.
Popular amenities for The Villages holiday rentals
Other great holiday rentals in The Villages
The Swift Fox
The Villages, De La Vista West 1762
By Eastport and near Middleton/Sawgrass with Cart
SUNSATIONAL!!
Newer Villa in The Villages near Brownwood
The Villages, Heated Pool Walk to Sawgrass
Ideal location! 3/2 Stetson model w/4 man golfcart
Perfect Home in The Villages!
When is the best time to visit The Villages?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $277 NZD | $303 NZD | $289 NZD | $223 NZD | $199 NZD | $189 NZD | $178 NZD | $173 NZD | $182 NZD | $190 NZD | $215 NZD | $225 NZD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°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 970 holiday rentals in The Villages
Verified guest reviews
Over 15,100 verified reviews to help you choose
Family-friendly holiday rentals
720 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 460 rentals that welcome pets
Holiday rentals with a pool
310 properties feature pools
Rentals with dedicated workspaces
470 properties have a dedicated workspace
Wi-Fi availability
800 of The Villages holiday rentals include Wi-Fi 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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