We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Family-friendly vacation rentals in Winter Haven

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winter Haven

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

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Home in Winter Haven

4.89 out of 5 average rating, 261 reviews

The Old Haven - An Enduring Piece of Nostalgia

This charming home was built in 1908 and is located 45 minutes from Tampa/Orlando. Fully furnished, this space is perfect for families and friends providing plenty of space to sleep 8 people comfortably. With games, puzzles and Dvds, backyard fun for kids while the parents watch from the porch. Enjoy downtown entertainment within walking distance! Home is centrally located to dining, shopping, and small town fare. 4 bar restaurants walking distance on the lake. Live music from Lake sometimes.

Jul 24 – 31

ﺩ.ﺇ554 per night

Home in Haines City

4.95 out of 5 average rating, 140 reviews

Luxury Home 4/3 near Disney, 2 Masters

Luxury 4 bedroom home located in a quiet, gated community about 15 miles from Disney World. The travel time to Disney will depend on the traffic but is usually between 30 and 40 minutes. Fully furnished with 2 master King bed suites, one queen bedroom and one bedroom with 2 twin beds. 3 full baths. 5 high definition televisions, high speed Wifi, free long distance phone calls to US, Canada and UK. Large pool and spa. Large game room with many games and activities for children of all ages.

Apr 29 – May 6

ﺩ.ﺇ723 per night

Home in Lakeland

4.91 out of 5 average rating, 121 reviews

Central Lakeland Home Convenient to Parks & Sports

My historic home is waiting for you! Open, modern space w/ 2 bedrooms + bonus room, back porch & all the amenities needed for a short stay or staycation. Walk Lk. Hollingsworth, tour FSC campus, easily travel to Disney, Busch Gardens, LEGOLAND, Lk. Myrtle Sport Complex, and more! Close to downtown, the location is perfect for guests visiting for Detroit Tigers Spring Training, or the Sun 'n Fun Fly In. Enjoy a quiet brick paved street, away from noisy traffic, but close to everything in town.

Jul 17 – 24

ﺩ.ﺇ481 per night

Cottage in Polk City

4.85 out of 5 average rating, 199 reviews

Cozy Historical Cottage

This lovely cottage of 1,000 sqft of living space, two bedrooms, one bath, dining room. Enjoy the view from the patio overlooking the backyard or relax in the Florida room on a traditional swing. The Van Fleet Trail and Freedom Park are just a few yards away. Popular attractions like Fantasy of Flight, Dinosaur World, Lego Land, and Disney are nearby. The Lakeland Mall is 10 minutes away movies & restaurants. Just a short walk away you'll find two family restaurants. Book your stay today!

Dec 15 – 22

ﺩ.ﺇ315 per night

Cottage in Lake Wales

4.88 out of 5 average rating, 109 reviews

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

Apr 26 – May 3

ﺩ.ﺇ481 per night

Home in Davenport

4.93 out of 5 average rating, 200 reviews

Family pool villa - 20 minutes to Disney!

This family-friendly pool villa includes: • FREE Parking, • FREE High-speed WiFi, • FREE In-villa laundry facilities, and • A fully equipped kitchen! Located in the beautiful gated community of Tuscan Hills. GREAT LOCATION Golf: 3min Disney World: 15-20min Universal Studios: 45min SeaWorld: 20min Discovery Cove: 20min Legoland: 45min Kennedy Space Center: 75min Beaches: 90mi GREAT SHOPPING International Premium Outlets, 189 stores: 35min Vineland Premium Outlets, 160 stores: 25min

Apr 24 – May 1

ﺩ.ﺇ563 per night

Condo in Davenport

4.92 out of 5 average rating, 379 reviews

Mediterranean Resort! 2+2 Condo. 10 mins to Disney

Tuscana Resort Orlando is a Mediterranean-style villa resort minutes from DisneyWorld. Universal, Sea World & LEGOLAND are close as well. The amenities are top notch with a beautiful swimming complex that includes pool, hot tub, cabanas, kiddie pool, fitness centre etc. The very spacious 2-bed/2-bath condo is 1200sqft! Recently renovated/painted/new stainless steel appliances! Sleeps 8. Tile Throughout! Gorgeous Kitchen! 55” Smart TVs. FREE WIFI/Cable/Netflix. A/C. Washer/Dryer.

Feb 11 – 18

ﺩ.ﺇ547 per night

Home in Babson Park

4.97 out of 5 average rating, 108 reviews

Authentic "Old Florida" on Crooked Lake!

Authentic "Old Florida" on Crooked Lake! Surrounded by palmettos and Florida foliage, our 1930's rustic lakehouse is serene, private, and exceptionally relaxing. Spring-fed Crooked Lake is designated an "Outstanding Florida Waters" lake and is great for swimming, paddle boarding, kayaking, fishing, and waterskiing. Huge screen porch, ping pong table, fully-equipped kitchen, dining room table for 12, spacious living area (great for games) -- you won't want to leave!

Jun 19 – 26

ﺩ.ﺇ1,070 per night

Guest suite in Kissimmee

4.86 out of 5 average rating, 568 reviews

Private Studio in POOL home

Hello! We offer a portion of our home with a King sized bed, a large private bathroom with a Jacuzzi tub, and a Harry Potter play area accessed by rock climbing wall. The mini kitchen has a microwave, bread toaster, coffee maker, and refrigerator. There's an internet TV in the apartment with access to Prime. The pool and garden areas are shared with my family and another set of travelers. We are happy to offer our studio with a 5-star cleanliness rating.

Jan 17 – 24

ﺩ.ﺇ249 per night

Home in Auburndale

4.94 out of 5 average rating, 146 reviews

Lake Whistler Beach House with lakefront pool

The Lake house is a resort with Paddle boards/Kayaks at no cost to our guests. Enjoy the entire yard and non-public lake with a private beach which offers you fishing and water sports (jet skis are additional). The main house has a pool table,air hockey and live darts! Also there is a BBQ, 4 TV's, cable, internet, movie library and washer/dryer, Pool and pool Jacuzzi. Small fenced back yard for pets (pet fee required).

Aug 16 – 23

ﺩ.ﺇ1,346 per night

Guesthouse in Lakeland

4.98 out of 5 average rating, 214 reviews

Modern lakeside retreat by SEU and FSC

This 1/1 lakefront historic cottage, built in 1920, is separate from the main house with its own entrance, parking, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks and fishing poles are provided for your enjoyment during your stay. Come unwind and enjoy the lake views from the hammock and private beach!

Jun 10 – 17

ﺩ.ﺇ407 per night

Guest suite in Winter Haven

4.96 out of 5 average rating, 259 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. Fishing available on site. New dock just finished with plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door, horse paddocks and patio overlooking the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

Mar 7 – 14

ﺩ.ﺇ419 per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Winter Haven family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Apartment in Davenport

4.86 out of 5 average rating, 243 reviews

Recently Award Winning Renovated 2+2 Near Disney

Oct 21 – 28

ﺩ.ﺇ455 per night

Townhouse in Kissimmee

4.94 out of 5 average rating, 181 reviews

New Resort near Orlando Disney Private Hot Tub

May 15 – 22

ﺩ.ﺇ546 per night

Condo in Champions Gate

4.85 out of 5 average rating, 262 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

Jan 9 – 16

ﺩ.ﺇ473 per night

Home in Davenport

4.94 out of 5 average rating, 172 reviews

Star Wars Villa - 5 Bed/4 Bath Star Wars/Frozen Home Private Pool/Spa (Pool Heat Included)

Jan 10 – 17

ﺩ.ﺇ761 per night

Townhouse in Kissimmee

4.97 out of 5 average rating, 281 reviews

Find a Little Magic in a Townhouse near Disney and Universal

Aug 18 – 25

ﺩ.ﺇ674 per night

Condo in Kissimmee

4.94 out of 5 average rating, 300 reviews

Disney World Condo w/ Full Kitchen, Balcony & Pool

Jul 28 – Aug 4

ﺩ.ﺇ430 per night

Condo in Orlando

4.97 out of 5 average rating, 108 reviews

Lakefront Resort Condo near Disney & Universal

Jan 17 – 24

ﺩ.ﺇ677 per night

Apartment in Kissimmee

4.87 out of 5 average rating, 268 reviews

King Bed Family Condo Orlando Disney Universal

Oct 7 – 14

ﺩ.ﺇ400 per night

Family- and pet-friendly home rentals

Home in Orlando

4.85 out of 5 average rating, 124 reviews

The Prince House w/Free Parking (Central Location)

Aug 18 – 25

ﺩ.ﺇ477 per night

Townhouse in Kissimmee

4.88 out of 5 average rating, 246 reviews

Disney fireworks new house - 5 minutes to Disney

Nov 17 – 22

ﺩ.ﺇ383 per night

Guesthouse in Windermere

4.94 out of 5 average rating, 240 reviews

Small Guesthouse near Orlando's Theme Parks

Mar 18 – 25

ﺩ.ﺇ495 per night

Villa in Kissimmee

4.78 out of 5 average rating, 409 reviews

7BD with Movie Theater Pool & Jacuzzi near Disney!

Sep 2 – 9

ﺩ.ﺇ1,187 per night

Home in Kissimmee

4.89 out of 5 average rating, 145 reviews

Luxury Disney Vacation Home on Reunion Golf Resort

Dec 14 – 21

ﺩ.ﺇ2,047 per night

Condo in Kissimmee

4.83 out of 5 average rating, 170 reviews

Disney Adorable Condo in the heart of it ALL! 1/1

Feb 2 – 9

ﺩ.ﺇ428 per night

Home in Kissimmee

4.89 out of 5 average rating, 178 reviews

PrivateJacuzzi-BBQ-ResortPool-Gym-7mlsDisney

Nov 2 – 9

ﺩ.ﺇ606 per night

Apartment in Orlando

4.91 out of 5 average rating, 319 reviews

Orlando Vacation Condo - 3bed/2bath

Aug 24 – 31

ﺩ.ﺇ726 per night

Family-friendly home rentals with a pool

Home in Davenport

4.81 out of 5 average rating, 131 reviews

Welcoming fully equipped villa in Davenport

Sep 2 – 9

ﺩ.ﺇ500 per night

Home in Davenport

4.86 out of 5 average rating, 205 reviews

Disney World Area Villa Orlando * Pool * Sleeps 10

Nov 8 – 15

ﺩ.ﺇ564 per night

Cottage in Kissimmee

4.96 out of 5 average rating, 423 reviews

Bright & Cozy Cottage Near Disney

Feb 1 – 8

ﺩ.ﺇ383 per night

Guest suite in Kissimmee

4.83 out of 5 average rating, 513 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Aug 8 – 15

ﺩ.ﺇ277 per night

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

Oct 30 – Nov 6

ﺩ.ﺇ441 per night

Home in Davenport

4.9 out of 5 average rating, 200 reviews

Disney Area Luxury Villa with Private Pool

Sep 23 – 30

ﺩ.ﺇ529 per night

Cottage in Kissimmee

4.94 out of 5 average rating, 372 reviews

Entire Cottage close to Disney, Universal, Airport

Jul 19 – 26

ﺩ.ﺇ388 per night

Home in Davenport

4.79 out of 5 average rating, 102 reviews

Mintra’s Villa Pool & Spa

Sep 11 – 18

ﺩ.ﺇ537 per night

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

Total rentals
210 properties
Wifi availability
210 properties include access to wifi
Rentals with dedicated workspaces
120 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
80 properties allow pets
Total number of reviews
7.7K reviews

Destinations to explore