Family-friendly holiday rentals in Wildwood

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.

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!

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.

Villages-Private Heated Pool-Central Location

Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

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!

Embers Place | Modern! | Private! | Arcade! | New!

🏡 Charming 4-Bedroom Retreat in Ocala, FL – Ideal for Families, a Couples Getaway 💑 & Groups 👯‍♀️! Welcome to our new, beautifully appointed home ✨ located in the heart of Ocala, Florida 🌴. This spacious 4-bedroom, 2-bathroom retreat offers the perfect blend of comfort 🛋️, luxury & convenience, close to I-175, making it an ideal getaway for anyone seeking a peaceful escape!

3/2 Courtyard Villa in The Village of Citrus Grove

Get comfortable and enjoy plenty of extra room at this spacious home. Large courtyard with a patio and lanai to soak in the Florida weather, open & spacious floor plan, TVs in both living room and master bedroom, and more! Only minutes away from Ezell recreation center and Homestead recreation center; close to pickleball, pools, classes, golfing, etc.

Brand New! Modern Guesthouse!

New Morden gateway! This guesthouse is located in the peaceful community of Lake Panasoffkee and located just one hour from Walt Disney World and Orlando. One hour to Tampa/Busch Gardens/Clearwater/Sarasota. The suite is a beautiful queen size bedroom, 1 bath, kitchen and a living room with a fold-out couch. This suite includes 2 smart TV's and Wi-Fi.

Peaceful Cottage in the Heart of Wildwood

Peaceful home... -Full kitchen for cooking any meal. -Pet friendly with $25 pet fee per dog. No cats please. -Keurig coffee maker for that morning cup of joe. -WiFi and smart tv. -Washer and dryer available for use. -Large lanai with a fenced in backyard for privacy. -Close to all amenities. -One mile from The Villages!