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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.

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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.

Home in Haines City

4.95 out of 5 average rating, 139 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.

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!

Cottage in Lake Wales

4.88 out of 5 average rating, 107 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.

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

Condo in Davenport

4.92 out of 5 average rating, 377 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.

Home in Davenport

4.81 out of 5 average rating, 131 reviews

Welcoming fully equipped villa in Davenport

A lovely villa located in central Florida with the Parks and other entertainment all within driving distance. 3 bedrooms and 3 bathrooms with large south facing pool/spa and a lanae providing some shelter and a games room for the wet days. The villa is comfortably furnished and has a fully equipped kitchen. Other amenities include wifi, cable and phone, so we hope you have everything you could possibly need to make your stay a home from home, and enjoy the villa as we do.

Cottage in Kissimmee

4.94 out of 5 average rating, 371 reviews

Entire Cottage close to Disney, Universal, Airport

A full cottage for 4! The perfect place stay. Located just 20 minutes from Disney and Universal. Shopping and Restaurants are less than 5 minutes from the cottages. All new furnishings, fresh linens, fresh paint! Privately owned. This cottage is our favorite!!! We also just updated the A/C. Check out unit We also have three other cottages on property, the Bitty Bungalow, Bitty Bliss, and the Bitty Blossom. All cottages are within 70 yards of each other.

Guest suite in Kissimmee

4.86 out of 5 average rating, 567 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.

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).

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!

Guest suite in Winter Haven

4.96 out of 5 average rating, 257 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)

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Popular amenities for Winter Haven family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Condo in Champions Gate

4.85 out of 5 average rating, 262 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

Condo in Kissimmee

4.84 out of 5 average rating, 249 reviews

Lake View Family Condo Disney Universal Orlando

Townhouse in Davenport

4.92 out of 5 average rating, 202 reviews

Disney Villa at Regal Palms*Near Pool/Lazy River

Condo in Orlando

4.97 out of 5 average rating, 296 reviews

Luxurious Waterfront Resort near Disney &Universal

Apartment in Orlando

4.9 out of 5 average rating, 313 reviews

Beautiful View, Newly Renovated 1 Mile to Disney

Condo in Orlando

4.91 out of 5 average rating, 406 reviews

Cozy Cay Condo Convn Ctr Vista Cay 2BR 2Ba 4 bds

Apartment in Davenport

4.83 out of 5 average rating, 120 reviews

Penthouse 3 beds Bahama Bay resort

Townhouse in Kissimmee

4.95 out of 5 average rating, 161 reviews

Beautiful family home near all attractions.

Family- and pet-friendly home rentals

Home in Lakeland

4.82 out of 5 average rating, 130 reviews

Florida Lake View With Private Pool And Fishing

Townhouse in Kissimmee

4.92 out of 5 average rating, 226 reviews

Beautiful Farm House Decor near Disney, Sleeps 6

Home in Lakeland

4.91 out of 5 average rating, 121 reviews

Central Lakeland Home Convenient to Parks & Sports

Home in Orlando

4.85 out of 5 average rating, 124 reviews

The Prince House w/Free Parking (Central Location)

Villa in Kissimmee

4.87 out of 5 average rating, 142 reviews

Minutes from Disney Gated LakeView Pvt Heated Pool

Villa in Kissimmee

4.78 out of 5 average rating, 406 reviews

7BD with Movie Theater Pool & Jacuzzi near Disney!

Condo in Kissimmee

4.83 out of 5 average rating, 170 reviews

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

Villa in Kissimmee

4.92 out of 5 average rating, 181 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

Family-friendly home rentals with a pool

Guest suite in Kissimmee

4.83 out of 5 average rating, 509 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Home in Davenport

4.87 out of 5 average rating, 109 reviews

Sandy Ridge Villa, Large South Facing Pool & Spa

Cottage in Kissimmee

4.96 out of 5 average rating, 421 reviews

Bright & Cozy Cottage Near Disney

Condo in Kissimmee

4.92 out of 5 average rating, 263 reviews

Beautiful Beach Style Condo minutes from Disney

Home in Davenport

4.92 out of 5 average rating, 241 reviews

Orlando Disney area home

Home in Kissimmee

4.79 out of 5 average rating, 256 reviews

3 bedroom Orlando Florida pool home

Home in Davenport

4.79 out of 5 average rating, 102 reviews

Mintra’s Villa Pool & Spa

Home in Davenport

4.86 out of 5 average rating, 205 reviews

Disney World Area Villa Orlando * Pool * Sleeps 10

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

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