Family-friendly holiday rentals in Wildwood

Luxe 2BR in The Villages | Mins to Eastport Square

Enjoy the best of The Villages in this cozy, prime spot. You’ll be just minutes away from the best shopping, dining, & local buzz. ■7 mins to Eastport Town Sq. ■5 mins to Sawgrass Grove ■10 mins to Middleton ■8 mins to Saluki Rec Center This home is furnished with premium furniture throughout. The kitchen is fully equipped with all you need for a nice stay, & each bedroom is well appointed with its own TV & ensuite bathroom. Please note that a $50 charge is applicable to get the lifestyle ID

Latitude Adjustment

Change your latitude in this beautiful two bedroom, two bathroom Patio Villa in The Villages. Located in the Village of Newell, this spacious and modern home has everything you need to make your stay relaxing and fun, including a golf cart! Enjoy a cup of coffee from the Keureg after your morning stroll on one of the nearby nature trails. Pools, pickleball and golf are all five minutes by golf cart, along with dining and entertainment at Sawgrass Grove and twelve minutes to the new Eastport!

The Villages Retreat- Free Coffee, Brand New!

Welcome to The Villages Retreat, a charming house nestled in the heart of Moultrie Creek Village! This delightful property boasts three bedrooms, providing ample space for a comfortable stay, perfect for families or groups visiting to watch their grandkids sports games, or to celebrate their graduation! This Home is Centrally Located and is within 5 minutes from locations such as: The Villages Charter Highschool and it's stadiums, The Tracy Performing Arts Center, and East Port Town Square.

King-Sized Comfort

Take a break and unwind at this peaceful oasis.Welcome to your serene getaway in The Villages! This spacious “Hideaway” in peaceful DeLuna offers 2 king beds, 2 baths, and easy access to pools, pickleball, tennis, and more. Explore over 130 miles of golf cart paths in this vibrant 55+ community featuring 700+ golf holes, 100+ pools, and endless clubs and activities. Just an hour from Orlando’s theme parks and near cruise ports, it’s the perfect mix of fun, comfort, and Florida sunshine!

Newer Villa in The Villages near Brownwood

Kick back and relax in this calm, stylish new villa in the Villages. It is within walking or a 3 minute golf cart ride to Brownwood Town Center where there are dining, shopping and nightly music. It is also near Lake Okahumpka Recreation Center where you can fish or kayak. This area has beautiful nature trails for walking or biking with separate golf cart paths. There is a neighborhood pool and other amenities nearby. It also comes with a complementary golf cart for your convenience.

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!

Opal Oasis in The Villages

Want a newer vacation home close to Sawgrass Grove where free nightly entertainment is available, several pools, recreation centers, biking paths and the town square of Eastport? Look no further. Check out this fully furnished home! The outdoor living is relaxing and tropical as we have an outside patio behind the palms. It will make you feel like the only person on the street! The home is within a 12 minute drive to the Villages High school/ Middleton and 18 minutes to Leesburg

Marsh Bend Waterview Oasis in The Villages

Picture yourself staying at our Sanctuary overlooking the peaceful water view in the Village of Marsh Bend. Take a short stroll across the street to Edna's Beer & Wine Garden or enjoy the nearby pool or Pitch N Putt. This beautiful, ultra clean, new home can be your next oasis and you enjoy preparing a meal in the beautiful kitchen with all of the necessities. 3 Bedrooms and 2 Bathrooms give you plenty of room to enjoy the house for yourselves or have a few guests.

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.

Tiny Hobbit cabin on lovely Fort Brook Horse Farm

Hi everyone! This little cabin is a bedroom with a queen size bed. It is camping. It includes coffee maker,pods Cream , Sugar. It has a/c electricity and a lamp. The restroom and showers are Close by. You have a fire pit that is a grill and table and chairs just out front. You might want to grab some wood and match light charcoal makes cooking on the grill easier. You are welcome to pet the horses and goats. We allow well behaved dogs that are leashed.

The Coconut Lounge 3/2 w/ Hot Tub & Pool Table

Beautifully renovated 3-bed, 2-bath home in The Village of De Soto—perfectly positioned between timeless favorites and the newest hotspots! Enjoy a spacious game room with a POOL TABLE, board-game glass table, cozy couch, and big-screen TV. Relax in the new birdcage with a HOT TUB and plush seating. The enclosed backyard welcomes one small dog (with pre-approval only) for a stay everyone will love.

Begonia on the Bend – Stylish Home Near Sawgrass

🌴 Modern 3BR/2BA Begonia-style home in The Villages’ new Cason Hammock neighborhood. Built in 2021, this spacious 2,083 sq ft retreat features an open layout, oversized garage + golf cart garage, and stylish comfort throughout. Walk to Sawgrass Town Square, McGrady’s Pub, pool, rec center, and Fresh Market. Enjoy The Villages lifestyle with everything you need for a relaxing stay!