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Kid-friendly holiday rentals in Winter Haven

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Winter Haven

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

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Condo in Orlando

4.86 out of 5 average rating, 288 reviews

BreathtakingView-1BR/2BA-1 MILE TO DISNEY-Sleeps 6

Located 1 mile to Disney Springs in a Gated-Community A NEWLY REFURBISHED Spacious 1-bedroom, 2-bath Condo in Lakefront luxury @ Blue Heron Beach Resort nestled on shores of 400+ acre Lake Bryan, 2 blocks off I4 @ Lake Buena Vista exit. This luxurious condo overlooks the Pool & Lake Bryan. Sleeps 4 It’s all here! The ultimate Walt Disney World vacation right here at your fingertips! From the best of Disney or Work Travel this property offers the perfect environment to spend a lifelong memory

Guest favourite

Holiday home in Kissimmee

4.86 out of 5 average rating, 37 reviews

BEST HOUSE! Marvel, Princesses, Potter, StarWars

The best Orlando homes, under 10 minutes (2 miles) from Disney's Maingate! "Happily Ever After" Luxury Playhouses sleep up to 20 guests in 8 bedrooms, 4 of which are gorgeous King Master Suites with 5 stunning bathrooms. Fully stocked kitchen with Mickey dinnerware! Magical HARRY POTTER 3D home theater with Oculus/XBOX/PS4. STAR WARS, ENCANTO, MOANA, & CINDERELLA rooms full of toys & costumes for all ages/sizes! The tropical LITTLE MERMAID Pool & Hot Tub are always heated to your comfort!

Home in Kissimmee

4.9 out of 5 average rating, 52 reviews

Free Pool Heat! Baby Safe w *Indoor PlayGround*

*Free POOL HEAT*Close to Disney Parks! Home equipped for baby! Full nursery, double stroller, highchair, packnplay, outlet covers, baby gates, toys, books, bouncy, and more. Kids love the Toy Story indoor playground with ball-pit, trampoline & slide, the fun doesn't stop at Disney! 6 themed bedrooms (3 Kids & 3 Adult themes), 5 baths, appliance stocked kitchen, a movie/game loft w/ 2 queen sofa sleepers, in-ground pool and Jacuzzi with BABY GATE! Fully furnished high-end patio and pool area.

Townhouse in Kissimmee

4.85 out of 5 average rating, 159 reviews

"The Haven" Newly Remodeled Luxury Townhome

This amazing townhome has recently been upgraded by the new owner to make it an even more impressive vacation rental. Over $20,000 was spent to upgrade beds, mattresses, all linen, towels, decor and many of the appliances. The home is completely modern and updated to impress any traveler to the area. The children will be wowed by the stunning Avengers loft/game room and the themed Toy Story and Harry Potter bedrooms. If all that wasn`t enough, the home is just 100 yards from the clubhouse.

Townhouse in Kissimmee

4.87 out of 5 average rating, 110 reviews

Orlando Disney new House at Resort with lake view!

Renewed house in Resort with fantastic lake view and an Amazing Clubhouse. (NO resort fees) | 1 min | Old Town Kissimmee | 3 min | Publix® | 3 min | McDonald's®, Wendy's®, Miller's Ale House® and much more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | Premium Outlet® I-4 | 9 min | DISNEY® AREA (All Parks) | 10 min | ESPN Sports | 10 min | Convention Center | 14 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 60 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Guest favourite

Home in Winter Haven

4.96 out of 5 average rating, 91 reviews

Glass Haven: Serene Getaway 7 min from Legoland!

Come relax with your whole family in this peaceful home! Our 2 bedroom 2.5 bathroom home is very spacious and can accommodate up to 7 people. Enjoy your day only 7 minutes to LEGOLAND. You will have pool access as well as access to many board games and arcade games within the home. Fun for the whole family! Our home is wheelchair accessible with an elevator that goes between floors so your family can accommodate well if needed! We do not allow parties. The home is strictly no-smoking.

Guest favourite

Condo in Kissimmee

4.95 out of 5 average rating, 153 reviews

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Guest favourite

Apartment in Kissimmee

4.86 out of 5 average rating, 218 reviews

Modern Great Villa near Disney & Parks

This place is 5 up to 20 minutes to all of orlando's amusement and water parks!. One of the best units in this resort, just book and see for yourself. An excellent unit with great reviews. There is an awsome pool and jacuzzi onsite (Please note, sometimes the jacuzzi breaks down and may not work during your stay). high speed wifi. easy smooth self checkin with a private keypad code that is being replaced between each new guest, walking distance to many shops and plazas, free parking.

Guest favourite

Townhouse in Kissimmee

4.91 out of 5 average rating, 55 reviews

Modern Family Friendly 3 bed 2.5 bath Townhome!

Welcome to our stylish, family-friendly getaway that can comfortably host up to 6 guests! Gated community with 24-hour security. This stunning home offers a lot! Notable mentions include • Modern, baby-friendly amenities • Resort pool and kids splash pad • Outdoor covered children’s play area • Clubhouse and gym • Conveniently located near world-famous attractions Ideal for an unforgettable vacation with your loved ones. Check in 4pm, check out 11am. NO CHECKOUT CHORES!

Guest favourite

Townhouse in Kissimmee

4.93 out of 5 average rating, 183 reviews

Beautiful family home near all attractions.

Beautiful, spacious and impeccable townhome close to all parks and entertainment with resort amenities. We follow Airbnb's enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights: *We sanitize high-touch surfaces, down to the doorknob. *We use cleaners and disinfectanst approved by global health agencies, and We wear protective gear to help prevent cross-contamination. *We clean each room using extensive cleaning checklist.

Guest favourite

Townhouse in Davenport

4.93 out of 5 average rating, 56 reviews

Disney Theme Home, Resort Access, Waterpark

themed bedrooms, private pool, and resort access 👙heated ameinities pool 💦water slide 💧lazy river 🏐volleyball 🌟themed rooms: Night Before Christmas, Shrek, and Beach 🍹Tropical Tiki Hut 🕹️ Game Arcade 🍦Ice Cream Parlor Less than 20 min drive: Old Town , Disney World , Fun Spot America 🌺ACTIVITIES/ATTRACTIONS ★ 🌴Walt Disney World Resort 🌟Universal Studios Florida 🌺LEGOLAND Florida Resort ⛳️ChampionsGate Golf Club 🌴Orlando Tree Trek Adventure Park

Home in Lakeland

5 out of 5 average rating, 4 reviews

Family-Friendly | Fire-pit | Pool Table & Soccer

Nestled in a serene neighborhood, our cozy duplex home sleeps 7 with 2 queen beds and a bunk bed. Enjoy a fire pit, soccer, and pool table in the private backyard. Private parking adds convenience. Perfectly located, explore Disney World, Legoland, Busch Gardens, and the beautiful beaches of St. Petersburg & Clearwater, all just a short drive away. A perfect base for a memorable Florida adventure!

Holiday rentals for every style

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Popular amenities for Winter Haven kid-friendly rentals

Free parking on premises

Air conditioning

Child-friendly house rentals

Guest favourite

Home in Lakeland

4.99 out of 5 average rating, 74 reviews

Sleep and play near downtown

Guest favourite

Home in Kissimmee

4.91 out of 5 average rating, 126 reviews

Disney closeby, Pool, Spa,Themed Game, Pets OK

Guest favourite

Home in Davenport

4.97 out of 5 average rating, 35 reviews

Funtastic 1 Level 5/4, Near Disney Free Resort&BBQ

Home in Clermont

4.8 out of 5 average rating, 15 reviews

Silver creek getaway

Home in Davenport

4.86 out of 5 average rating, 7 reviews

Disney! Orlando ChampionGates

Guest favourite

Home in Davenport

4.91 out of 5 average rating, 11 reviews

Modern Legends, Near Disney, kings bed ste

Guest favourite

Home in Davenport

4.9 out of 5 average rating, 20 reviews

Heated Pool | Mickey, Simpsons, Forest | Disney

Guest favourite

Home in Kissimmee

4.87 out of 5 average rating, 97 reviews

Hotel Style comfortable Beds

Kid-Friendly apartment rentals

Apartment in Kissimmee

4.74 out of 5 average rating, 184 reviews

King Bed First Floor Family Condo Disney Universal

Guest favourite

Apartment in Kissimmee

4.94 out of 5 average rating, 166 reviews

Lovely one bedroom apartment.

Guest favourite

Apartment in Florida Center

4.96 out of 5 average rating, 27 reviews

Premier Resort One Bedroom APT Next to Universal

Guest favourite

Apartment in Lakeland

4.9 out of 5 average rating, 247 reviews

Downtown Lakeland - 2 bed/1bath Luxury Apartment

Guest favourite

Apartment in Kissimmee

4.93 out of 5 average rating, 56 reviews

Apartment Close to Disney, Parks and Shopping

Guest favourite

Apartment in Winter Haven

4.92 out of 5 average rating, 126 reviews

Quint & Cozy, Confidently Clean Apartment

Apartment in Kissimmee

4.89 out of 5 average rating, 167 reviews

Spacious 3 Bedroom 4 miles to Disney Great Resort

Guest favourite

Apartment in Davenport

4.9 out of 5 average rating, 101 reviews

Remodeled, cozy 1 Bedroom apartment near Disney

Child-Friendly Holiday Condos

Guest favourite

Condo in Kissimmee

4.97 out of 5 average rating, 115 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

Guest favourite

Condo in Kissimmee

4.93 out of 5 average rating, 108 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

Condo in Kissimmee

4.79 out of 5 average rating, 201 reviews

Condo near Disney Orlando 3 Bdr

Guest favourite

Condo in Kissimmee

4.92 out of 5 average rating, 115 reviews

Disney Lux Resort - 2BR w/ Pool, Hot Tub & Lanai

Guest favourite

Condo in Kissimmee

4.92 out of 5 average rating, 111 reviews

Cozy single story condo near Disney

Condo in Kissimmee

4.82 out of 5 average rating, 116 reviews

Lovely 3BR 2BA condo, great amenities and location

Guest favourite

Condo in Kissimmee

4.89 out of 5 average rating, 196 reviews

Marvelous apartment near Disney first floor

Condo in Kissimmee

4.85 out of 5 average rating, 163 reviews

One in a Minion condo your kids will love +450Mbps

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

Total rentals
100 properties
Nightly prices starting at
$64 AUD before taxes and fees
Total number of reviews
5.9K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore