Family-friendly vacation rentals in Wildwood

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.

Pool and fun right out back

Bring the family to this beautiful place with lots of room for fun. With the Waterlily Rec Center right out back you can walk to the family pool in just a few steps. Pickle ball, exercise equipment, corn hole, bocce ball, shuffleboard and a walking/biking path is all right out the back door. A golf cart is included for golfing and access to the rest of The Villages. 1 minute to the Waterlily golf cart bridge and 8 minutes to Brownwood Square. Or Edna’s on the Green is just a few minutes away.

Whole House-sleeps 10 The Villages Spanish Springs

Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

Robin's Song in Brownwood

WELCOME to the beautiful ROBIN's SONG conveniently located in The Village of Atwood where you are just minutes from all the fun and activities in The Villages. Just a 2 minute ride on the Yamaha GOLF CART (extra charge) into the famous BROWNWOOD PADDOCK SQUARE where you will enjoying shopping, dinning and live music each evening from 5 to 9 p.m. Just a minute ride to THE GRAND TRAVERSE PLAZA housing Publix, or the relaxing Brownwood Hotel and Day spa featuring the Wolfgang Puck Restaurant.

Waters Edge, ¼ mile to Eastport, 3 BR, 2 bath

Welcome to this brand-new 3BR/2BA home, perfectly located 1/4 mile from Eastport Town Square in The Villages! Enjoy a modern, comfortable stay w/ a king bed in the primary suite, two queen bedrooms, & smart TVs throughout. The new kitchen features stainless appliances, quartz counters, & all your cooking essentials. Fast Wi-Fi and an in-unit washer/dryer. Relax outside on the furnished huge lanai, or explore amazing nearby amenities: Waters Edge Pool & Rec Center Bellaire Executive Golf

Perfect "get-away" home for a couple or family!

Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. Golf cart included in price for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

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.

Newest Hotspot in The Villages Eastport/Middleton”

Welcome to Eastport! The Villages’ most exciting new lifestyle destination — Eastport! Whether you're visiting for a weekend getaway or an extended stay, this beautifully furnished 2-bedroom, 2-bath Patio Villa w/golf cart puts you in the heart of everything The Villages has to offer — golf, pickleball, shopping, dining, entertainment, recreation, and serene nature. From the moment you arrive, you’ll see why Eastport is the new standard for luxury, leisure, and active adult living.

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.

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.

5 Springs Close Goats Chicken Free Eggs Memories

COME PLAY AND PET THE GOATS! 5 natural springs 4 to 10 minutes away Fur Babies WELCOME FREE Farm Fresh Eggs Feed the Chickens NO ROOSTERS! Fire pit (we set up the wood daily) Tree swing/bench swing Cornhole Grills Picnic pavilion 5 Acres 2 King Beds 1 Twin pull-out 1 Full size pullout Fully stocked kitchen. Disney 40 min Rock Springs 3 min Kings Landing, Kelly Park, Wekiwa Springs, Barrel Springs, and Wekiva Springs are all less than 5 MILES away. Wekiva Island is a must-visit!

Golf Cart Included, In the Heart of The Villages

Stay in the heart of The Villages, just minutes from Brownwood Square and top-rated golf courses! This charming home offers a short walk to Manatee Family Pool, and easy access to dining, shopping, and entertainment. Relax in a well-appointed space with modern amenities and a private patio. Whether you're here for tee time, exploring the local attractions, or unwinding in Florida’s sunshine, this vacation haven is perfect for your getaway!