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Family-friendly holiday rentals in Winter Haven

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Winter Haven

  • Total holiday rentals

    Explore 260 holiday rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 12,270 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 110 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wi-Fi availability

    260 of Winter Haven holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Haven rentals

  • 4.8 Average rating

    Winter Haven stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Winter Haven

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

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Guest favourite
Three thoroughbred horses graze peacefully on a lush green pasture. The area is surrounded by tall trees, providing shade and a natural backdrop. A glimpse of a trailer can be seen in the background, indicating the farm's working environment.
Guest suite in Winter Haven

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. The dock has plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door. Please note there is no barrier around pool and all children (anyone under age of 18)must be supervised at all times. Guests must swim at their own risk. You may see horses in the paddocks. The pool deck overlooks the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

Indoor spacesFamilyAmenities

4.95 out of 5 average rating, 314 reviews
Top Guest favourite
The exterior of the home features a sleek black façade with large windows allowing natural light in. A neatly landscaped yard includes tropical plants and colorful foliage, enhancing the inviting entrance. The driveway leads to a single-car garage, with ample space to welcome guests.
Home in Winter Haven

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Just 6 miles to Legoland! This stylish home is perfect for vacation. 2 ensuite bedrooms, 2 additional rooms and 2 additional semi private sleeping areas there is room for everyone. Every space is newly furnished with stylish pieces and comfortable beds. The pool area is fully screened so you can enjoy the Florida weather without the bugs. The open concept space is perfect for large groups and families and the kitchen is ready for you to make a meal. A laundry room houses a washer and dryer.

FamilyKitchenBarbecue

4.99 out of 5 average rating, 147 reviews
Guest favourite
A large outdoor space features a private pool surrounded by loungers in blue and a shaded dining area. A patio table with chairs is placed in the foreground, while a safety fence encloses the pool area, providing a secure environment.
Home in Winter Haven

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

Indoor spacesKitchenLayout

4.98 out of 5 average rating, 123 reviews
Guest favourite
The indoor area features colorful Lego-themed decor, including a bed covered with a vibrant quilt, and a comfortable sofa with bright cushions. A TV is mounted on the wall. A refrigerator and kitchen area are visible, with a game table and playful rug adding to the lively atmosphere.
Tiny home in Winter Haven

Tiny Lego Home

Tiny Lego home just 12 minutes from Legoland/Peppa pig. Everything to keep the kids entertained. Massive playground and dining/ grilling area, Large outdoor Lego building area, Indoors every thing Lego. Wall legos, table legos and more. If you like Legos this is the place to stay. The kids will be in Lego heaven! Recently added swimming pool with deck and soccer field in playground area. The outdoor playground park is a shared space for any guests who may be staying at complex.

KitchenIndoor spacesCheck-in

4.92 out of 5 average rating, 162 reviews
Top Guest favourite
A view of the blue lake house is presented with a well-manicured lawn leading up to it. The house is framed by mature trees, providing shade. A wooden walkway extends toward the entrance, while the serene lake is visible in the background.
Cottage in Eagle Lake

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

KitchenFamilyCheckout

4.99 out of 5 average rating, 310 reviews
Guest favourite
A serene backyard features a clear swimming pool surrounded by a tiled deck. Sun loungers are positioned around the pool, with a shaded dining area beneath a striped umbrella. Lush greenery and tall trees provide a natural backdrop, enhancing the outdoor space.
Home in Cypress Gardens

Florida Oasis w/ Pool near LEGOLAND

We have added a modern twist to the design of this 1950's home with all the modern appliances and finishes. This home is nestled in-between 2 lakes among the Winter Haven Chain of Lakes! The backyard is a Florida Oasis of a great pool and pool deck with plenty of fun available with games for you and the kids, or just enjoy laying peacefully in the sun! 2.5 mile drive from Legoland 3.5 mile drive from Downtown Winter Haven with great restaurants and small town unique shops.

KitchenFamilyComfort

4.79 out of 5 average rating, 350 reviews
Guest favourite
An outdoor dining area is shown under a shaded pergola, featuring a large table surrounded by comfortable chairs. The spacious pool is visible in the background, with a patio area adorned with colorful tiles. Lush greenery frames the scene, adding a tranquil vibe.
Home in Cypress Gardens

4/2 House near Legoland w Optional Heated Pool

Relax with the whole family at this peaceful home in Winter Haven 5mins to Legoland and the new Peppa Pig theme park, perfect for your next family vacation! Right across the street from lake Ned park with lake View from the front porch and office, bring your small water toys as there is a public boat ramp across the street. There are many restaurants as well as a Publix grocery store all within 2 miles from the home! Downtown winter haven is a short 10 minute commute.

KitchenIndoor spacesBathroom

4.95 out of 5 average rating, 107 reviews
Guest favourite
An inviting swimming pool is surrounded by a spacious patio area, featuring lounge chairs and a shaded table with an umbrella. The serene view of Little Lake Otis and lush greenery is visible in the background under a partly cloudy sky.
Home in Winter Haven

Legoland Lakehouse Canoe & Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

KitchenFamilyRiver

4.91 out of 5 average rating, 222 reviews
Top Guest favourite
A charming lake home is showcased with a light-coloured façade and blue shutters. A welcoming entrance is flanked by decorative chairs, with well-maintained landscaping featuring green grass and flower beds enhancing the outdoor appeal.
Home in Winter Haven

Lake View, Game Room, 10 min Legoland

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby!

Indoor spacesFamilyWalkability

4.98 out of 5 average rating, 124 reviews
Top Guest favourite
A private backyard features a clean in-ground pool surrounded by a paved patio. Two lounge chairs are positioned beside the pool, and a dining set with four chairs sits nearby. Lush greenery and a white privacy fence enhance the serene outdoor setting.
Home in Cypress Gardens

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 11 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

KitchenIndoor spacesComfort

4.97 out of 5 average rating, 148 reviews
Guest favourite
The exterior of the tiny house is showcased, featuring a welcoming front porch with steps leading up. Landscaping includes vibrant tropical plants and a stone pathway. The structure is set against a clear blue sky, highlighting the charming design and inviting ambiance.
Tiny home in Cypress Gardens

4 a Tiny House w/ Bunk Bed in Quiet Marina Unit 14

Our cozy tiny house is perfect for when less is more :-). An intimate space for a long reflective weekend or a more affordable option for a few days with the kids at nearby Legoland. Offering a queen-size Murphy bed and two additional single-size bunk beds, the Cypress Inlet Tiny House can comfortably accommodate up to four people. Equipped with a mini-fridge, a microwave, and a Keurig duo (drip & pod) coffee maker.

Indoor spacesFamilyTV

4.86 out of 5 average rating, 176 reviews
Top Guest favourite
A modern living area features a sectional sofa adorned with blue and white decorative pillows. A round coffee table with a marble top sits on a textured area rug. Natural light fills the space through sheer curtains, complemented by a stylish console table and a round mirror.
Home in Winter Haven

Cozy 3 bedrooms 2 bathrooms

Relax with the whole family at this peaceful and charming home in Winter Haven.This home is centrally located and is within walking distance to Lake Howard , downtown winter haven and plenty attractions We are located 10 minutes from Legoland, Peppa Pig Park, five minutes to Advent Health Fieldhouse, five minutes to Winterhaven Hospital, 45 minutes to Walt Disney World, SeaWorld and Busch Gardens.

Indoor spacesKitchenLocation

4.99 out of 5 average rating, 115 reviews

Popular amenities for Winter Haven family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
A cozy living area features a light brown sectional sofa and a matching sofa adorned with patterned cushions. A modern coffee table sits in the center, with a remote control placed on top. A large artwork of a character hangs above, flanked by two lamps.
Home in Winter Haven

Legoland Splash Escape (pool and hotub)

KitchenIndoor spacesComfort

4.89 out of 5 average rating, 137 reviews
Top Guest favourite
A screened-in pool area features a clear, inviting swimming pool surrounded by comfortable lounge chairs. A basketball hoop is positioned at one end of the pool, with a scenic view of the lake and trees visible through the enclosure.
Home in Haines City

Southern Dunes Lakeview Poolhome

KitchenFamilyDecor

4.96 out of 5 average rating, 102 reviews
Top Guest favourite
Home in Davenport

Magical 2 pool-Spa & Game Room Villa near “Disney”

KitchenIndoor spacesBackyard

4.97 out of 5 average rating, 144 reviews
Top Guest favourite
Home in Cypress Gardens

Adult-Only Retreat w/ Pool & Spa | 18+, Private

FamilyKitchenAir conditioning

4.98 out of 5 average rating, 133 reviews
Top Guest favourite
A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.
Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

FamilyKitchenPool

4.96 out of 5 average rating, 116 reviews
Superhost
A colorful bunk bed structure is featured, decorated in vibrant shades of yellow, blue, and orange. The mural backdrop depicts a jungle scene with a leopard and tropical plants, enhancing the playful atmosphere of the room. Spiral staircases offer access to the upper sleeping area.
Townhouse in Davenport

WaterPark+Arcade+KingBed+Hot Tub+NearDisney

KitchenFamilyPool

4.94 out of 5 average rating, 139 reviews
Top Guest favourite
Townhouse in Davenport

No Airbnb fees! Pvt Pool/GameRoom/Clubhouse 271521

Indoor spacesFamilyLaundry

4.99 out of 5 average rating, 161 reviews
Top Guest favourite
The exterior of a spacious home is presented, featuring a blue façade and a welcoming entrance. Lush tropical foliage surrounds the property, which is highlighted by palm trees and manicured lawns. A vibrant sunset casts colorful hues in the sky, enhancing the serene atmosphere.
Home in Winter Haven

Spectacular Waterfront Home in Winter Haven

FamilyIndoor spacesLocation

4.98 out of 5 average rating, 138 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A spacious outdoor area is visible, featuring a brick patio that opens towards a calm body of water. Nearby, a wooden dock extends into the water, surrounded by greenery and a few lounge chairs. A peaceful landscape is highlighted by gently waving trees.
Cabin in Haines City

Nearby Legoland,Disney,Universal,Seaworld and more

FamilyKitchenSleep quality

4.97 out of 5 average rating, 236 reviews
Guest favourite
An aerial view of a single-story home is presented, showcasing a well-maintained lawn and driveway. The surrounding neighborhood features a mix of greenery and residential structures, contributing to a welcoming suburban atmosphere.
Home in Winter Haven

Extra large home! Bring Your Boat & all the Toys!

KitchenFamilyComfort

4.95 out of 5 average rating, 101 reviews
Guest favourite
The themed bedroom features twin beds, designed to resemble spaceships, with bold, illuminated accents. A wall mural depicts a starry sky, while nearby, a gaming machine displays a classic arcade setup, creating an immersive atmosphere for guests.
Home in Davenport

Amazing Friends 5BR+Private Pool+Lazy River

KitchenIndoor spacesDecor

4.95 out of 5 average rating, 111 reviews
Superhost
A renovated house is framed by mature trees, displaying a fenced front yard that features a paved walkway leading to the entrance. The structure includes a simple facade with large windows, allowing natural light to enter the interior.
Home in Auburndale

three bedroom family house, near legoland

FamilyIndoor spacesWalkability

4.91 out of 5 average rating, 206 reviews
Guest favourite
Cabin in Lake Alfred

The Lake Alfred Citrus Wood Guest Cabin

FamilyKitchenCleanliness

4.94 out of 5 average rating, 307 reviews
Top Guest favourite
A charming white cottage is framed by a well-kept lawn, with a brick chimney visible on one side. Lush green shrubs and trees provide shade around the property, and a pathway leads to the entrance, suggesting easy access to the home.
Cottage in Davenport

Classic Cottage in country setting

Indoor spacesFamilySleep quality

4.99 out of 5 average rating, 132 reviews
Top Guest favourite
A themed bedroom inspired by 'Nightmare Before Christmas' features a decorative mural with a crescent moon and whimsical trees. The bed is adorned with vibrant bedding, and a warm light illuminates the room. A closet area displays themed decorations, enhancing the enchanting atmosphere.
Townhouse in Davenport

LazyRiver+WaterPark+KingBd+Arcade+HotTub

FamilyIndoor spacesCheckout

4.94 out of 5 average rating, 143 reviews
Top Guest favourite
A modern lakefront home is showcased with a clean, spacious facade. Well-maintained landscaping features palm and leafy plants, complementing the beige exterior. A curved driveway leads to a two-car garage, with panoramic views of the lake apparent beyond the property.
Home in Cypress Gardens

Winter Haven Waterfront Retreat

KitchenFamilyComfort

5.0 out of 5 average rating, 42 reviews

Family-friendly home rentals with a pool

Guest favourite
A well-maintained villa is showcased, featuring a welcoming entrance with a single-car garage. Lush greenery and colorful shrubs line the brick pathway, while tall palm trees and vibrant landscaping enhance the cheerful exterior. Bright clouds are visible in a clear blue sky.
Villa in Haines City

Sandy's Southern Dunes Villa

Indoor spacesKitchenWi-Fi

4.86 out of 5 average rating, 181 reviews
Top Guest favourite
The exterior of the home features a light-colored facade with a welcoming entrance. A neatly landscaped yard includes vibrant green shrubs and a palm tree. The driveway leads to a single-car garage with a white door, set against a backdrop of clear blue skies.
Home in Haines City

Southern Dunes Villa - Pool - Golf - near Disney

Indoor spacesFamilyAir conditioning

4.91 out of 5 average rating, 202 reviews
Guest favourite
Home in Haines City

Breathtaking Home

KitchenFamilyWalkability

4.89 out of 5 average rating, 133 reviews
Superhost
A serene lakefront scene captures a sparkling pool surrounded by palm trees at sunset. The sky features vibrant hues of orange and purple, reflecting in the calm water. Two lounge chairs are positioned beside the pool, creating a peaceful retreat.
Guesthouse in Winter Haven

The Russell Lake House

FamilyIndoor spacesComfort

4.87 out of 5 average rating, 285 reviews
Guest favourite
A two-story, tropical style home is showcased, featuring a vibrant exterior in warm shades. A Tesla is parked prominently in the driveway, with lush palm trees and greenery flanking the entrance. The garage is accessible, contributing to the property's inviting curb appeal.
Home in Haines City

Luxury Tropical Themed Villa With Lake View!

KitchenIndoor spacesAccuracy

4.92 out of 5 average rating, 111 reviews
Top Guest favourite
Home in Haines City

Harry Potter's 6bd 6.5ba Hogwarts Experience

KitchenFamilyValue

4.96 out of 5 average rating, 104 reviews
Guest favourite
Home in Cypress Gardens

Legoland Escape

KitchenFamilyBathroom

4.9 out of 5 average rating, 31 reviews
Guest favourite
A vibrant bunk room includes four bunk beds and a cozy seating area with a pink canopy. An arcade game machine offers entertainment options, while a pool area features loungers and colorful striped decor. The bathroom presents a bright shower curtain and inviting tub.
Home in Cypress Gardens

Family Fun: Pool, Arcade Games

FamilyIndoor spacesQuiet

4.88 out of 5 average rating, 50 reviews

When is the best time to visit Winter Haven?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$255 NZD$275 NZD$278 NZD$271 NZD$253 NZD$251 NZD$238 NZD$232 NZD$224 NZD$229 NZD$248 NZD$256 NZD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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