Family-friendly vacation rentals in Wildwood

4.98 out of 5 average rating, 172 reviews

The exterior of a converted Chinook helicopter is showcased, featuring a fenced area and a welcoming entryway. The surrounding landscape includes greenery and sky, with details of the helicopter's design visible, blending seamlessly into the natural setting.

Plane in Brooksville

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!

KitchenFamilyCleanliness

A private outdoor area features a heated pool and spa, surrounded by screen enclosure. Comfortable seating is arranged beside the pool, complemented by an outdoor dining setup. The space is designed for relaxation with a stylish stone paver patio and clear blue skies above.

4.93 out of 5 average rating, 15 reviews

Pool and Spa Luxury Retreat

Escape to this charming 3BR/2BA home in The Villages, FL! Enjoy a private heated pool & spa, perfect for relaxation. Walk to the nearby recreation center or take a short 1-mile ride to Eastport. This home includes a 4-person golf cart, making it easy to explore all The Villages has to offer. Comfortably furnished with modern amenities, it’s ideal for a peaceful retreat or an active getaway. Book now for the perfect blend of convenience and leisure! Heating of the pool and spa included in rate.

FamilyIndoor spacesGetting around

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.

4.97 out of 5 average rating, 97 reviews

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.

Indoor spacesKitchenGrill

The exterior of a single-story home is showcased, featuring a well-maintained lawn and a gravel pathway. A seating area with chairs is positioned on the front porch. The garage is visible on the right, and colorful clouds are present in the evening sky.

4.91 out of 5 average rating, 23 reviews

Incredi-Bill Jo's

Get ready for an incredible stay at our Incredi-Bill Jo's stylish and cozy pool home. You'll be steps away from world class shopping, dining, entertainment, sports, recreation and GOLF. This three bedroom home is close to all of the amenities that make The Villages the number one destination for active adults year after year. And to make your stay even more incredible, you'll have the convenience and use of a beautiful golf cart! Come and see what all the fuss is about!

Indoor spacesFamilySleep quality

4.96 out of 5 average rating, 102 reviews

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

Your NEW home includes a very comfortable KING BED and GOLF CART!! With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house NOVA WATER filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!! 2 SMALL DOGS OK.

KitchenIndoor spacesTV

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.

5.0 out of 5 average rating, 110 reviews

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. One 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.

Indoor spacesFamilyAccuracy

5.0 out of 5 average rating, 20 reviews

Eastport Emerald Escape 2BR Luxury in Well Point

Escape to The Eastport Emerald 🌴, a luxurious 2-bed, 2-bath villa in The Villages' Village of Well Point. This bright, open-concept home is ideal for snowbirds, vacationers, and extended stays, featuring 1GB fiber Wi-Fi, a chef's kitchen with gas range, and a private screened lanai. Enjoy self check-in with smart lock 🔑, community pools 🏊, lake access, and waterfront walking paths. Just a golf cart ride ⛳️ to Eastport Square and Sawgrass Grove.

KitchenHospitalityComfort

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.

5.0 out of 5 average rating, 31 reviews

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.

FamilyKitchenGrill

5.0 out of 5 average rating, 259 reviews

Guesthouse in Lady Lake

Cute & Cozy Tiny Guesthouse

Take it easy at this cozy and peaceful getaway located in a safe and quiet neighborhood near The Villages. It's conveniently located all within 1.5 miles to Walmart, Aldi, Waffle House, McDonald's, Pizza Hut, Cracker Barrel, BJ's Wholesale and many other shops and restaurants. Plus, The Villages Hospital. We are also located two miles from The Villages Spanish Springs town square which has free entertainment from 5pm to 9pm every night of the week.

FamilyIndoor spacesValue

5.0 out of 5 average rating, 9 reviews

New Home! Wildwood Area

Welcome to your perfect Florida getaway! This cozy and comfortable home in Wildwood offers the ideal place to relax while staying just minutes from The Villages, local restaurants, shopping, and beautiful outdoor attractions. 5 miles away from Brownwood Paddock Square. Whether you’re visiting family, exploring Central Florida, or enjoying the vibrant lifestyle of The Villages, this home provides a peaceful and convenient stay.

Indoor spacesCleanlinessHospitality

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.

4.96 out of 5 average rating, 158 reviews

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

Indoor spacesKitchenBreakfast

5.0 out of 5 average rating, 11 reviews

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 spacesFamilyLaundry

Popular amenities for Wildwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.92 out of 5 average rating, 148 reviews

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

Indoor spacesFamilyValue

Place to stay in The Villages

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.

5.0 out of 5 average rating, 127 reviews

Safari themed private addition with pool/hot tub.

KitchenIndoor spacesDecor

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

4.81 out of 5 average rating, 252 reviews

Woodpecker Treehouse Retreat

Indoor spacesFamilyAccess

4.88 out of 5 average rating, 216 reviews

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

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 236 reviews

An outdoor porch features a two-person Jacuzzi, inviting relaxation while overlooking a lake. Warm lighting is provided by lanterns, creating an ambient atmosphere against the backdrop of a colorful sunset and silhouettes of trees.

Tiny home in Dade City

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

FamilyIndoor spacesHot tub

4.97 out of 5 average rating, 109 reviews

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 spacesBathroom

4.93 out of 5 average rating, 147 reviews

Cottage in Clermont

Private Country House | 16 Guests | Gatherings

Indoor spacesFamilyAccess

5.0 out of 5 average rating, 136 reviews

Home in Davenport

Themed Disney Villa | Pool | Arcade | Resort ºoº

FamilyKitchenGetting around

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 352 reviews

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

FamilyIndoor spacesComfort

4.99 out of 5 average rating, 172 reviews

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

FamilyIndoor spacesAccuracy

A decorative sign is mounted on the wall, featuring a blue background with white text that reads 'welcome to our happy place.' The sign is framed in a simple wooden border, adding a homey touch to the interior.

4.81 out of 5 average rating, 116 reviews

Carlton Courtyard Villa - Walk to Sumter Landing

KitchenIndoor spacesPool

4.97 out of 5 average rating, 119 reviews

Two golf carts are parked on the driveway of a villa, one black and one red. Lush greenery, including palm trees, enhances the front yard, which is well-maintained and features a blend of grass and decorative plants. A clear blue sky and sunshine create a bright atmosphere.

Villa in The Villages

Villa 2 Master Suites/2 Golf Carts Great Location

Indoor spacesFamilyBackyard

The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.

4.97 out of 5 average rating, 105 reviews

Fabulous Courtyard Villa close to Sumter Landing

Indoor spacesKitchenCleanliness

4.97 out of 5 average rating, 183 reviews

The cabin is surrounded by lush greenery, positioned on a private peninsula. A spacious deck with seating faces the water, offering a serene view of the canal. Natural light filters through the trees, illuminating the inviting structure.

Cabin in Floral City

Private Waterfront Cabin Retreat with Kayaking

KitchenFamilyOutdoor spaces

4.97 out of 5 average rating, 205 reviews

Cottage in Coleman

Romantic Escape on Peaceful Mini Farm

KitchenIndoor spacesView

4.98 out of 5 average rating, 410 reviews

A wooden door with a pointed roof stands surrounded by lush green foliage. The door features two windows with sheer curtains, providing a glimpse of the natural surroundings, while a stone pathway leads up to it, enhancing the inviting entrance.

Farm stay in Ocala

Tiny Hobbit cabin on lovely Fort Brook Horse Farm

FamilyKitchenBreakfast

Family-friendly home rentals with a pool

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.

4.98 out of 5 average rating, 113 reviews

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

FamilyKitchenBathroom

4.86 out of 5 average rating, 274 reviews

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!

Indoor spacesFamilyValue

Superhost

5.0 out of 5 average rating, 3 reviews

Htd Pool & Attached Hot Tub. Rare corner propty

FamilyKitchenHospitality

A charming home exterior showcases a light blue facade and a white picket fence, surrounded by vibrant landscaping. A two-car garage is positioned prominently, with decorative plants adding interest. The clear blue sky provides a bright backdrop, accentuating the inviting appearance of the house.

4.97 out of 5 average rating, 38 reviews

Brownwood Square - Villages Home

Indoor spacesFamilyGetting around

The exterior of a modern single-story home is showcased at twilight, featuring a neatly landscaped front yard with tropical plants. A cozy seating area is visible by the entrance, and a two-car garage complements the home’s facade under a colorful sunset sky.

4.83 out of 5 average rating, 12 reviews

King-Sized Comfort

Indoor spacesKitchenLocation

Superhost

5.0 out of 5 average rating, 5 reviews

Heated Pool + GOLF CART - Village of Santiago!

AccuracyCleanlinessHospitality

5.0 out of 5 average rating, 10 reviews

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

Indoor spacesFamilyAmenities

The kitchen features modern stainless steel appliances and a large island with seating for four. The quartz countertops complement the rich cabinetry and vibrant blue wall. Pendant lights provide illumination, enhancing the sleek design of the space.