Family-friendly vacation rentals in Wildwood

4.98 out of 5 average rating, 173 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!

KitchenIndoor spacesAccuracy

5 out of 5 average rating, 7 reviews

Home in Sumterville

2BR Mins to Pools & Eastport | Middleton | Patio

Unwind in this cozy 2BR retreat in the heart of The Villages. Just 5 mins to Eastport Town Square, 7 mins to Middleton, & 4 mins to Saluki Recreation. You’re minutes from the area’s best shopping, dining, golf courses and entertainment. This home is fully set up for an easy, comfortable stay with a well-equipped kitchen, spacious bedrooms each with its own TV and private ensuite, and a peaceful patio to relax and unwind. Please note that a $50 charge is applicable to get the lifestyle ID.

AccuracyQuietCheck-in

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 spacesFamilyNearby

4.86 out of 5 average rating, 276 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!

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!

FamilyIndoor spacesBiking

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

Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

FamilyKitchenCheck-in

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 out of 5 average rating, 127 reviews

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!

KitchenIndoor spacesValue

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

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.

FamilyKitchenHospitality

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.

4.99 out of 5 average rating, 124 reviews

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!

FamilyIndoor spacesQuiet

4.96 out of 5 average rating, 103 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.

KitchenFamilyHospitality

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 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 spacesKitchenComfort

5 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 spacesSleep quality

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 spacesFamilyPets

Popular amenities for Wildwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 111 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

Indoor spacesFamilyBeach

4.98 out of 5 average rating, 102 reviews

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!

KitchenIndoor spacesLayout

4.85 out of 5 average rating, 100 reviews

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

KitchenIndoor spacesCheck-in

4.96 out of 5 average rating, 170 reviews

A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.

Home in Orlando

Spacious Home with Pool & Hot Tub near Downtown

FamilyKitchenLocation

4.94 out of 5 average rating, 111 reviews

Home in Crystal River

Peaceful Oasis*Near Springs*Game Rm*Spa*Boat Pkg

KitchenFamilyCondition

4.99 out of 5 average rating, 123 reviews

Home in Kissimmee

5BR Mario& Princess Peach•Pool•Theater•Free Resort

KitchenFamilyAccuracy

4.88 out of 5 average rating, 217 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 spacesKitchenCleanliness

4.99 out of 5 average rating, 174 reviews

Farm stay in Pierson

Ruby Oaks Farm w/ Beach Near St. JohnsRiver

KitchenFamilyPool

Family- and pet-friendly home rentals

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 spacesWalkability

4.97 out of 5 average rating, 184 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

Indoor spacesKitchenComfort

4.87 out of 5 average rating, 104 reviews

A charming cottage exterior is framed by lush greenery and palm trees, with a white picket fence surrounding the property. The light blue façade features several windows and a welcoming front door. The well-maintained landscape contributes to the property's inviting ambiance.

Home in Inverness

Dreamy River Cottage

FamilyIndoor spacesCheckout

4.99 out of 5 average rating, 144 reviews

A scenic view of a tranquil canal is presented, bordered by lush greenery. A wooden dock extends into the water, accommodating a boat. Nearby, comfortable outdoor seating is available, surrounded by natural landscaping, offering a peaceful outdoor space.

Home in Summerfield

Getaway on the Waterway- Dock+Kayaks+SUP board

FamilyIndoor spacesComfort

5 out of 5 average rating, 20 reviews

Eastport Emerald Escape 2BR Luxury in Well Point

KitchenNearbyCondition

4.95 out of 5 average rating, 174 reviews

A spacious living area is equipped with two reclining armchairs and a comfortable sofa, arranged around a glass coffee table. A flat-screen television is positioned on a white media console. Natural light filters in through large windows, enhancing the welcoming environment.

Home in Inverness

Inverness 2/2 Fenced Yard w/Hot Tub Availability

KitchenIndoor spacesTV

A single-story home is depicted in a well-kept neighborhood, featuring a manicured lawn with palm trees and shrubs. Two vehicles, including a golf cart, are parked in the driveway, while a cloudy blue sky provides a serene backdrop.

4.96 out of 5 average rating, 115 reviews

FREE Golf Cart + Fabulous Location + Classy Decor!

Indoor spacesFamilyDecor

4.99 out of 5 average rating, 173 reviews

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

FamilyKitchenSleep quality

Family-friendly home rentals with a pool

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.

5 out of 5 average rating, 26 reviews

Designer Home in The Villages, FL.

Indoor spacesFamilyBiking

4.85 out of 5 average rating, 132 reviews

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!

Indoor spacesKitchenCleanliness

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.

4.91 out of 5 average rating, 99 reviews

New, private pool getaway in The Villages, FL

FamilyIndoor spacesAir conditioning

A heated pool is enclosed within a screened patio, featuring gentle water features and surrounded by lush greenery. Two wooden adirondack chairs and a small side table are positioned nearby, inviting relaxation in this outdoor space.

4.9 out of 5 average rating, 20 reviews

The Villages | Heated Pool | Walk to Sawgrass!

FamilyKitchenValue

5 out of 5 average rating, 5 reviews

Heated Pool + GOLF CART - Village of Santiago!

CleanlinessHospitalityAccuracy

5 out of 5 average rating, 42 reviews

Newest Hotspot in The Villages Eastport/Middleton”

Indoor spacesKitchenPool

A clear blue pool is framed by a screened patio, offering a view of the home's outdoor kitchen and seating area. Comfortable lounge chairs surround the pool, with an umbrella positioned for shade. The backdrop features additional residential structures.

5 out of 5 average rating, 35 reviews

The Villages pool property with a 4-person cart

Indoor spacesKitchenBeach

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.