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Family-friendly vacation rentals in Wildwood

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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 G$6,275 GYD 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

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!

4.82 out of 5 average rating, 266 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!

5.0 out of 5 average rating, 128 reviews
Guest favorite
A single-story home is situated on a corner lot, surrounded by well-maintained lawns and landscaping. Large trees provide shade, while the blue sky creates a bright backdrop. A screened-in porch and patio area are visible on the side of the house.
Home in The Villages

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.

4.98 out of 5 average rating, 164 reviews
Top guest favorite
A screened-in patio features a refreshing private pool surrounded by lush landscaping. Two chaise lounges are positioned beside the water, while a float rests in the pool. A fountain adds a tranquil element to the relaxing outdoor space.
Home in The Villages

Casa Santin Luxury in The Villages w/Private Pool

A refined Florida Luxury home designed for effortless indoor-outdoor living, Casa Santin blends modern coastal style with relaxed comfort—creating the perfect escape for your next getaway. Your Private Oasis. The highlight of Casa Santin is the stunning screened lanai and private pool—your own resort-style sanctuary. Start your mornings with coffee in the sunshine, spend afternoons poolside, and unwind in the evenings with a western sunset, a glass of wine under the soft glow of the lanai.

4.97 out of 5 average rating, 97 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!

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.

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.

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.

5.0 out of 5 average rating, 115 reviews
Top guest favorite
A spacious living area is highlighted by a large, L-shaped sectional sofa with patterned pillows, surrounded by two blue armchairs. A round wooden coffee table sits centrally on a decorative rug, while natural light flows through windows that offer a view of the outdoors.
Home in The Villages

VIEW-T-FUL! w/Golf cart

Stunning entry with one of a kind picturesque setting and unbeatable location all in one. This lanai was redesigned with no support columns to have this spectacular highly desirable panoramic golf front & water view. Sweeping view of Southern charm, cluster of mature oak trees with Spanish moss. The back of the home facing the morning sunshine lighting up the lanai and screen area for a fine morning of relaxation. Don't hesitate, this home has it all, golf cart too!

4.99 out of 5 average rating, 124 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.

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.

5.0 out of 5 average rating, 6 reviews

Popular amenities for Wildwood family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
Cottage in Clermont

Private Country House | 16 Guests | Gatherings

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

4.88 out of 5 average rating, 218 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

4.85 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

4.97 out of 5 average rating, 111 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

4.94 out of 5 average rating, 101 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

4.97 out of 5 average rating, 105 reviews
Top guest favorite
An outdoor space features a heated swimming pool beside a lanai. A table with chairs and a television is situated under the screened roof, while a hot tub is positioned nearby. Two inflatable rings float in the clear water, surrounded by potted plants.
Home in Citrus Springs

Private Spa *Heated Pool* & Firepit Near Manatees!

4.98 out of 5 average rating, 106 reviews
Top guest favorite
Farm stay in Pierson

Ruby Oaks Farm w/ Beach Near St. JohnsRiver

4.99 out of 5 average rating, 174 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

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

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

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

Updated Villages Getaway Sumter Landing&Golf Cart

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!

4.99 out of 5 average rating, 176 reviews
Guest favorite
A single-story house with light-colored siding is shown under a clear blue sky. A paved driveway leads to a garage, while a golf cart is parked nearby. Neatly trimmed bushes line the front of the home, contributing to a well-maintained exterior.
Home in The Villages

Close to Lake Sumter with Golf Cart!

4.93 out of 5 average rating, 110 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

4.8 out of 5 average rating, 137 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

4.96 out of 5 average rating, 156 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

4.96 out of 5 average rating, 355 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

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

4.94 out of 5 average rating, 103 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

4.91 out of 5 average rating, 99 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

5.0 out of 5 average rating, 61 reviews
Top guest favorite
Home in Wildwood

Stylish Villages Getaway

5.0 out of 5 average rating, 12 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

5.0 out of 5 average rating, 20 reviews
Guest favorite
The exterior of a newly constructed home features a light color palette with a modern design. A spacious driveway leads to a three-car garage, flanked by neatly trimmed greenery and a landscaped yard under a clear blue sky.
Home in The Villages

The Villages-3 bd (3 king)/3 full ba+Cart NEW HOME

4.97 out of 5 average rating, 73 reviews
Guest favorite
A spacious home is showcased amidst lush landscaping, featuring multiple palm trees and colorful shrubs. The exterior highlights a warm yellow facade with a welcoming front porch. A clear blue sky with scattered clouds adds to the inviting atmosphere of the property.
Home in The Villages

The Grandview

4.76 out of 5 average rating, 38 reviews

When is the best time to visit Wildwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,442 GYDG$43,299 GYDG$41,835 GYDG$30,539 GYDG$24,892 GYDG$24,892 GYDG$21,963 GYDG$21,126 GYDG$21,754 GYDG$24,473 GYDG$28,029 GYDG$30,748 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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