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Family-friendly vacation rentals in Wildwood

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Wildwood

  • Total vacation rentals

    Explore 1,040 vacation rentals in Wildwood

  • Nightly prices starting at

    Wildwood vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 15,810 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 430 rentals that welcome pets

  • Vacation rentals with a pool

    420 properties feature pools

  • Rentals with dedicated workspaces

    640 properties have a dedicated workspace

  • Wi-Fi availability

    1,040 of Wildwood vacation rentals include wi-fi 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!

Top-rated family-friendly rentals in Wildwood

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Superhost
A modern living area features a spacious sectional sofa in gray, complemented by a wooden coffee table. The open floor plan connects to a kitchen with stainless steel appliances and seating for four at the bar. Decorative wall elements add interest to the neutral walls.
Home in Lake Panasoffkee

Heated Pool & Kayaking House in Lake Panasoffkee

Bring the whole family to this great place with lots of room for fun. Enjoy this stylish house very close to the lake. Create new memories while staying at this beautiful property and all its amenities such as an indoor pool with nature view. Designed play room with pool/hockey air table and so much fun. With lake access from the its yard and 5 minutes from all restaurants and entertainments at Lake Panasoffkee. This fully renovated house will make your trip a unique and unforgettable experience

KitchenFamilyBackyard

4.85 out of 5 average rating, 117 reviews
Superhost
A treehouse elevates above the ground, surrounded by lush greenery and lit by soft string lights. A cozy fire pit area with wooden seating is positioned beneath the treehouse, inviting gatherings in a natural setting. The space emphasizes tranquility and connection with nature.
Treehouse in Ocala

Woodpecker Treehouse Retreat

Take some time for yourself and enjoy the treehouse, you will marvel at nature, you will be surrounded by beautiful birds of different types, explore the place just 10 minutes from Santos Trailhead and 35 from Rainbow Springs. After you finish visiting Ocala and seeing its incredible recreational areas, enjoy our hot tub with hydro massage, relax in our hanging mesh, gather around the fire pit and make s'mores. Our Treehouse promises the perfect blend of nature's tranquility and modern comfort!

FamilyIndoor spacesSleep quality

4.82 out of 5 average rating, 268 reviews
Top guest favorite
An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.
Place to stay in The Villages

Safari themed private addition with pool/hot tub.

This special Guest house addition is Central to everything in The Villages! Making it easy to plan your visit. In The Village of Osceola Hills @ Soaring Eagle Preserve. Just North of Rt 44. A short golf cart or car ride to Brownwood Square & Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Play over 50 golf courses at a minimal fee, & free rec centers! We have an easy 4 seater Golf-cart rental , & request free Guest passes!

KitchenIndoor spacesCondition

5.0 out of 5 average rating, 128 reviews
Top guest favorite
Two goats are seen in a lush green field, one featuring a predominantly black coat with white markings, while the other is white with black patches. The surrounding grass is tall, contributing to the farm setting.
Ranch in Wildwood

Owl Cove Ranch Sunset Barn Apartment

Welcome to the Owl Cove Ranch barn apartment. This 10 acre farm is located on the wall of The Villages (Hammock of Finney) right off HWY 301 near city of Coleman. Newly renovated 4 Bedroom/2 Bathroom apartment with fully stocked kitchen. We currently have 9 goats, 4 Cows, 2 Donkey's and 4 chickens for the kids to experience the good old fashion farm. Watch beautiful Florida sunsets. Guest passes to the Villages are available with this rental to explore the amazing lifestyle of the Villages!

Indoor spacesFamilyAir conditioning

5.0 out of 5 average rating, 28 reviews
Top guest favorite
An elegantly appointed dining area is highlighted by a dark table surrounded by gray upholstered chairs. Two candles sit atop the table, with a decorative bowl in the center. Soft lights hang overhead, illuminating the blue walls adorned with framed art and decorative shelves.
Villa in The Villages

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!

Indoor spacesKitchenAmenities

4.86 out of 5 average rating, 278 reviews
Top guest favorite
Home in Wildwood

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.

FamilyKitchenDecor

5.0 out of 5 average rating, 42 reviews
Superhost
An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.
Villa in The Villages

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.

FamilyIndoor spacesHospitality

4.84 out of 5 average rating, 134 reviews
Top guest favorite
An aerial view showcases a spacious property surrounded by lush greenery. The home features a neat driveway and is complemented by several nearby buildings, including a recreation center with a pool. Sunlight highlights the rooftops and well-maintained lawns.
Home in The Villages

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 four-seater golf cart is included. It’s only minute to the Waterlily golf cart bridge and eight minutes to Brownwood Square. Or Edna’s on the Green is just a few minutes away.

FamilyIndoor spacesAccuracy

5.0 out of 5 average rating, 115 reviews
Guest favorite
A private heated pool is framed by a spacious lanai with a sleek, white deck. The pool features a shimmering blue surface and tiled border. Surrounding walls provide privacy while natural light pours in from above, creating a bright and inviting space.
Home in Wildwood

New, private pool getaway in The Villages, FL

The whole group will enjoy easy access to everything from this centrally located 3B/3BA home in the village of St Catherine. Just steps away from Sawgrass marketplace where you can enjoy dinner, nightly entertainment, pickle ball, and golf at the brand new Southern Oaks 18 hole championship golf If staying in is your idea of relaxation, enjoy the oversized lanai and private heated pool while watching your favorite shows or sports on the 65" smart TV.

KitchenIndoor spacesSleep quality

4.91 out of 5 average rating, 99 reviews
Top guest favorite
A living room is showcased with two blue sofas facing a glass coffee table. Soft lighting is provided by two table lamps and a large TV is positioned on a dark wood console. Colorful wall art adds brightness to the space, complemented by a dining area in the background.
Home in Wildwood

Private home in The Villages

Welcome to your perfect get-away in The Village of St. John’s. The cozy 3/2 villa is bright, fully equipped and comfortably furnished and includes guest passes. Enjoy the convenience of nearby shopping, dining and entertainment at Brownwood Paddock Square. Stroll on the walking trail which leads along Lake Okahumpka to the Recreation Center. Whether you’re here for excitement or relaxation, this is the perfect base for your stay in The Villages.

Indoor spacesKitchenAccess

5.0 out of 5 average rating, 31 reviews
Guest favorite
Home in The Villages

Htd Pool & Attached Hot Tub. Rare corner propty

New heated pool with attached hot tub and waterfall! Located in the coveted Village of Richmond, experience a rare rental retreat with stunning 270° water views and total privacy near Brownwood Square—minutes from shopping, dining, and medical facilities. Enjoy a breathtaking bird estuary sanctuary while relaxing in the new heated pool with attached hot tub, open-concept living with elegant finishes, and a fenced backyard oasis.

Indoor spacesKitchenLocation

5.0 out of 5 average rating, 6 reviews
Top guest favorite
Home in Wildwood

Stylish Villages Getaway

Welcome to your modern luxury escape in The Villages. Perfect for snowbirds, couples, or families, this brand-new home is designed for comfort and convenience. Enjoy high-end furnishings, elegant interiors, and access to resort-style community amenities. Make the most of your stay with a premium 6-passenger golf cart, electric bikes, and endless entertainment. Stay active, relax, and create unforgettable memories.

Indoor spacesFamilyPool

5.0 out of 5 average rating, 12 reviews

Popular amenities for Wildwood family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
An enclosed patio features a heated saltwater pool, accentuated by stone tile and decorative mosaic. Nearby seating options are visible, including a lounge chair under a shaded canopy. Lush greenery surrounds the area, providing a sense of privacy and tranquility.
Home in The Villages

Villages-Private Heated Pool-Central Location

Indoor spacesKitchenView

4.94 out of 5 average rating, 161 reviews
Superhost
A custom home is framed by lush greenery and mature trees. The landscaped yard features a manicured lawn, and the house showcases a welcoming façade with multiple windows, allowing natural light to enhance its inviting presence.
Home in Summerfield

A+ Privacy | Hot Tub | BBQ + Dining | Family +Pets

FamilyIndoor spacesAir conditioning

4.85 out of 5 average rating, 101 reviews
Guest favorite
The exterior of a spacious single-story house is visible, featuring a light-colored facade and a greenery-laden yard. A palm tree is seen in the foreground, while the driveway leads towards a garage on the right side.
Home in The Villages

Entire 3 BR Home(Sleeps 8)+Hot Tub in The Villages

FamilyIndoor spacesComfort

4.92 out of 5 average rating, 153 reviews
Top guest favorite
Cottage in Clermont

Private Country House | 16 Guests | Gatherings

KitchenIndoor spacesAccuracy

4.93 out of 5 average rating, 149 reviews
Guest favorite
A modern living space is illuminated by soft sunlight streaming through large windows. The wooden flooring creates a warm ambiance, while a sleek sectional couch and decorative partition subtly define the area. A potted plant adds a touch of greenery to the environment.
Home in Summerfield

Modern Lake Weir House

KitchenIndoor spacesCondition

4.88 out of 5 average rating, 218 reviews
Guest favorite
A vibrant bedroom is showcased with a tropical-themed quilt featuring large leaf patterns in teal and white. A decorative pillow with a starfish design is positioned on a spacious bed, complemented by a nightstand adorned with a small decorative palm tree.
Home in The Villages

3 BR 2 BA Coastal-vibe,Golf Cart,Pools, Pickleball

Indoor spacesFamilyAmenities

4.94 out of 5 average rating, 101 reviews
Guest favorite
A spacious outdoor area features a hot tub with bubbling water, surrounded by a screened patio. A swimming pool gleams in the sunlight, while a vibrant tree house play area with a slide and swing set adds a colorful touch to the yard.
Home in Spring Hill

TreeHouse, Swings, HotTub, HeatedPool, ClearSpring

KitchenIndoor spacesLayout

4.97 out of 5 average rating, 111 reviews
Guest favorite
The pool area is illuminated at night with vibrant lights, casting colorful reflections on the water. The curved shape of the pool is complemented by a spa and surrounded by lush greenery. A safety fence surrounds the space, enhancing privacy.
Home in Lecanto

Serene Paradise Heated Pool/HotTub/TikiBar 4 BR's

FamilyKitchenGetting around

4.97 out of 5 average rating, 105 reviews

Family- and pet-friendly home rentals

Guest favorite
A single-story home is showcased with a light exterior and an attached two-car garage. Neat landscaping featuring low-maintenance gravel and diverse shrubs surrounds the entrance. A clear blue sky and a few palm trees contribute to the inviting atmosphere of the property.
Home in The Villages

Walk to Sumter w/cart - Beautiful Courtyard Villa

Indoor spacesKitchenAir conditioning

4.89 out of 5 average rating, 118 reviews
Top guest favorite
Home in The Villages

King Bed, Golf Cart, Small Dogs & Water Filter!

Indoor spacesFamilyPool

4.96 out of 5 average rating, 105 reviews
Top guest favorite
Home in The Villages

Updated Villages Getaway Sumter Landing&Golf Cart

FamilyKitchenCleanliness

4.97 out of 5 average rating, 106 reviews
Top guest favorite
Home in The Villages

Private 3/2, 2 Golf Carts, Pizza Oven, Game Table!

Indoor spacesKitchenGetting around

4.99 out of 5 average rating, 176 reviews
Top guest favorite
A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.
Home in Lady Lake

Cozy Lady Lake Guest House

KitchenIndoor spacesPets

4.96 out of 5 average rating, 355 reviews
Top guest favorite
Guesthouse in Lady Lake

Cute & Cozy Tiny Guesthouse

FamilyIndoor spacesWifi

5.0 out of 5 average rating, 266 reviews
Top guest favorite
A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.
Home in The Villages

2/2 custom pool home with 4 person gas golf cart

Indoor spacesFamilyView

4.96 out of 5 average rating, 156 reviews
Guest favorite
The exterior of the home is framed by lush palm trees and neatly landscaped flower beds. A pathway leads to the entrance, featuring a covered porch with welcoming lights. The manicured lawn offers a serene atmosphere, complemented by well-placed outdoor lighting.
Home in The Villages

The Brownwood Brassie 3BR 2 Bath w/ Golf Cart

Indoor spacesFamilyComfort

4.8 out of 5 average rating, 137 reviews

Family-friendly home rentals with a pool

Top guest favorite
An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.
Home in The Villages

New Luxury Home-Pool-Waterfront View-3 King Suites

Indoor spacesFamilyOutdoor spaces

4.98 out of 5 average rating, 115 reviews
Top guest favorite
The image captures a welcoming street view of a residential area with charming homes featuring varied architectural styles. Lush palm trees and neatly trimmed shrubs outline the landscaped front yards. The sky is bright with fluffy clouds, contributing to the overall inviting atmosphere.
Home in The Villages

1199 Merryweather - Walk to Lake Sumter Sq 3nt min

FamilyKitchenOutdoor spaces

4.94 out of 5 average rating, 104 reviews
Top guest favorite
Home in Wildwood

Spotless 3BR Home w/ Golf Cart, Near Brownwood Sq

FamilyKitchenWalkability

5.0 out of 5 average rating, 11 reviews
Top guest favorite
A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.
Home in The Villages

Pirates & Parrots - The Villages - Golf Cart &Pool

KitchenIndoor spacesQuiet

5.0 out of 5 average rating, 61 reviews
Luxe
An expansive pool area features a sparkling blue pool and a relaxing spa surrounded by a screened enclosure. Lush green trees reflect in the tranquil pond visible beyond the outdoor space, creating a serene backdrop. Two comfortable lounge chairs sit nearby under a shaded awning.
Home in Wildwood

Poolside Paradise-w/ Pool & Golf Cart The Villages

Indoor spacesFamilyHot tub

5.0 out of 5 average rating, 21 reviews
Top guest favorite
A large outdoor pool is surrounded by a spacious deck, featuring neatly arranged lounge chairs. Palm trees are visible in the background, and a covered area with seating can be seen to the left. The sky features a mix of soft blue and wispy clouds.
Home in The Villages

2 min walk to pool, 4 seat cart, 5 min to Eastport

KitchenFamilyLong stay

5.0 out of 5 average rating, 20 reviews
Top guest favorite
A light-filled open-concept space features a modern kitchen with a central island and dining table, surrounded by decorative wall art. Large windows provide views of the outdoor area, enhancing the connection with nature. Stylish light fixtures hang from the ceiling, adding a contemporary touch.
Home in The Villages

Convenient Home in The Villages

KitchenIndoor spacesValue

5.0 out of 5 average rating, 26 reviews
Guest favorite
A modern single-story house is presented with a spacious driveway, flanked by lush green grass. A palm tree adds tropical appeal to the front yard, while a golf cart is parked to the left, contributing to the home's functional charm.
Home in The Villages

Villages-Waterfrnt, 3 king bds/2.5Ba+golf crt

KitchenIndoor spacesQuiet

4.95 out of 5 average rating, 73 reviews

When is the best time to visit Wildwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 657ﺩ.ﺇ 760ﺩ.ﺇ 735ﺩ.ﺇ 536ﺩ.ﺇ 437ﺩ.ﺇ 437ﺩ.ﺇ 386ﺩ.ﺇ 371ﺩ.ﺇ 382ﺩ.ﺇ 430ﺩ.ﺇ 492ﺩ.ﺇ 540
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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