
Family-friendly holiday rentals in Wildwood
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Wildwood
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

Remodeled 2/2 Baja style villa w/4 person cart
4 person, yamaha gas golfcart offered at this baja style 1000 sqft 2BR, 2BA courtyard villa! It comes fully furnished with pots, pans, linens, and does have a blow dryer and keurig! located in the De La Vista South area just off Morse, this villa is just a short cart ride to Spanish Springs or Sumter Landing. The villa has new stainless appliances, beautiful plank flooring, and fresh paint. King bed in the master, queen bed in the guest bedroom. All bedrooms have smart TV's, cable in LR only

Private Waterfront Cabin Retreat with Kayaking
Your private retreat on an acre nestled on a canal to the Withlacoochee River, wrapping around 2 sides of the property. Relax on your porch overlooking the water as you watch the birds and deer play. Kids will love the tire swing, toys such as Lego, Lincoln logs, pool table and ski ball. Kayaks available to our guests awaiting adventure. Bond around the fire pit, walk the trails, lounge in the hammocks, and fish on the dock. Setup the big screen to watch a movie. Welcome to your get-a-way!

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!

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.

HORSE FARM Retreat, Newer Built Private Guesthouse
Escape to our private guesthouse located in our peaceful but lively 7-acre farm with our family of horses, ponies, Guinea hens, ducks, roosters, chickens, bunnies, cats, & very lovable dogs. Enjoy grabbing fresh eggs, giving animals treats, puppies belly rubs, grilling, making s’mores at the fire pit, and enjoying the farm life! PLEASE read entire listing if little ones will be joining :-) NOTE: Our horses are not available for riding (see our guidebook for great alternate options)

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.

Serenity - In The Villages
Welcome to your dream retreat! This stunning Moonstone Home blends comfort, luxury, and convenience. Minutes from Eastport Square, Publix, and Fenney Rec Center, enjoy nature trails, pools, Fenney Grill, and executive golf—all accessible by golf car. Relax in the private lanai, cook in the chef’s kitchen, or watch SpaceX launches from your patio. With mossy oaks, stylish design, and top amenities, your perfect Villages getaway awaits. Book now and experience the magic!

Waterfront Cottage 2BR 1B
This charming house is located on nearly an acre of woodland. Fish from the dock of the screen room on the canal or kayak to the nearby lake. Relax in the private backyard Jacuzzi. Bike on the nearby Withlacoochee Trail. There are 2 bedrooms plus living room sleeper sofa, and a lanai with a day bed. Fully furnished. Orlando theme parks are 1 1/2 hour away, Busch Gardens 1 hour. Close to Weeki Wachee, Homosassa and Crystal River for manatee viewing or scallop season.

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.
Popular amenities for Wildwood family-friendly rentals
Family-friendly home rentals with a hot tub

Pet Friendly, Modern Tiny Home in Clermont!

Villages-Private Heated Pool-Central Location

Cute cottage-historic district-hot tub

LakeFront Villa-Jacuzi, Springs Manatees nearby

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Beautiful country house

Cozy Farmhouse Luxury/Pets Free/3 min I-75/Hot Tub

Luxury Container Home w/ Hot Tub- 30 min to Disney
Family- and pet-friendly home rentals

Cozy Cottage, private back yard, and free coffee!

Peaceful Cottage in the Heart of Wildwood

Lake Sumter 2/2 Villa FREE gas cart/Pet friendly

Pet-friendly retreat w/ fenced yard & pool

King Bed, Small Dogs OK, and 4-Seater Golf Cart!

Peace and Quiet

Patriotic Manatee Tiny House

Duck Haven - Wildlife Sanctuary - 5 miles to I75
Family-friendly home rentals with a pool

StJohns is a great area for golf, hiking, Kayaking

Sapphire Cottage - sleeps 6, on 5 acres with canal

Ocala Oasis-3 Bedrooms and Heated Pool!

Location Can’t be Beat! With cart!

Brownwood Square - Villages Home

A-Frame Cottage near Disney, Universal, & Lakes

Courtyard Villa On Golf Course w/Cart & Hot Tub

Robin's Song in Brownwood
When is the best time to visit Wildwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £123 | £133 | £129 | £100 | £87 | £81 | £77 | £74 | £77 | £86 | £99 | £108 |
| 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 |
Quick stats about holiday rentals that are family-friendly in Wildwood

Total holiday rentals
Explore 990 holiday rentals in Wildwood

Nightly prices starting at
Wildwood holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 14,760 verified reviews to help you choose

Pet-friendly holiday rentals
Find 430 rentals that welcome pets

Holiday rentals with a pool
380 properties feature pools

Rentals with dedicated workspaces
580 properties have a dedicated workspace

Wifi availability
990 of Wildwood holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wildwood rentals

4.9 Average rating
Wildwood stays are highly rated by guests – averaging 4.9 out of 5!
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- Family-friendly rentals Sumter County
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- Family-friendly rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
- Aquatica
- ICON Park
- Disney's Hollywood Studios
- Island H2O Live!
- Camping World Stadium
- Ocala National Forest
- ChampionsGate Golf Club
- Rainbow Springs State Park




