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Family-friendly holiday rentals in Winter Haven

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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.

22–29 Sep

€ 170 per night

Guest favourite

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.

8–15 Sep

€ 179 per night

Guest favourite

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.

16–23 Jul

€ 155 per night

Guest favourite

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!

22–29 Apr

€ 108 per night

Guest favourite

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.

26 Apr – 3 May

€ 147 per night

Guest favourite

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

19–26 Oct

€ 179 per night

Guest favourite

Apartment 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.

20–27 Feb

€ 161 per night

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.

19–26 Dec

€ 75 per night

Guest favourite

Cottage in Kissimmee

4.96 out of 5 average rating, 422 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

26 Mar – 2 Apr

€ 114 per night

Guest favourite

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).

15–22 Apr

€ 461 per night

Guest favourite

Guest house 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!

7–14 May

€ 125 per night

Guest favourite

Guest suite in Winter Haven

4.96 out of 5 average rating, 258 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)

27 Jul – 3 Aug

€ 119 per night

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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

Flat in Davenport

4.86 out of 5 average rating, 243 reviews

Recently Award Winning Renovated 2+2 Near Disney

21–28 Oct

€ 136 per night

Guest favourite

Flat in Davenport

4.83 out of 5 average rating, 121 reviews

Penthouse 3 beds Bahama Bay resort

23–30 Aug

€ 161 per night

Guest favourite

Apartment in Champions Gate

4.85 out of 5 average rating, 262 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

30 Sep – 7 Oct

€ 149 per night

Guest favourite

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)

10–17 Jan

€ 236 per night

Guest favourite

Apartment in Orlando

4.97 out of 5 average rating, 297 reviews

Luxurious Waterfront Resort near Disney &Universal

2–9 Sep

€ 195 per night

Guest favourite

Apartment in Kissimmee

4.94 out of 5 average rating, 300 reviews

Disney World Condo w/ Full Kitchen, Balcony & Pool

28 Jul – 4 Aug

€ 132 per night

Guest favourite

Flat in Kissimmee

4.87 out of 5 average rating, 268 reviews

King Bed Family Condo Orlando Disney Universal

27 Oct – 3 Nov

€ 126 per night

Guest favourite

Townhouse in Kissimmee

4.97 out of 5 average rating, 281 reviews

Find a Little Magic in a Townhouse near Disney and Universal

7–14 Nov

€ 212 per night

Family- and pet-friendly home rentals

Guest favourite

Home in Lakeland

4.82 out of 5 average rating, 130 reviews

Florida Lake View With Private Pool And Fishing

10–17 Aug

€ 278 per night

Guest favourite

Home in Orlando

4.85 out of 5 average rating, 124 reviews

The Prince House w/Free Parking (Central Location)

9–16 Aug

€ 145 per night

Guest favourite

Guest house in Windermere

4.94 out of 5 average rating, 240 reviews

Small Guesthouse near Orlando's Theme Parks

8–15 Jan

€ 152 per night

Townhouse in Kissimmee

4.79 out of 5 average rating, 222 reviews

Perfect home near Disney, Affordable & Comfortable

11–16 Nov

€ 129 per night

Guest favourite

Villa in Kissimmee

4.78 out of 5 average rating, 409 reviews

7BD with Movie Theater Pool & Jacuzzi near Disney!

5–12 Sep

€ 373 per night

Guest favourite

Home in Kissimmee

4.89 out of 5 average rating, 145 reviews

Luxury Disney Vacation Home on Reunion Golf Resort

5–12 Apr

€ 503 per night

Guest favourite

Home in Kissimmee

4.89 out of 5 average rating, 178 reviews

PrivateJacuzzi-BBQ-ResortPool-Gym-7mlsDisney

5–12 Sep

€ 166 per night

Apartment in Kissimmee

4.83 out of 5 average rating, 170 reviews

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

24–31 Mar

€ 131 per night

Family-friendly home rentals with a pool

Guest favourite

Home in Davenport

4.81 out of 5 average rating, 131 reviews

Welcoming fully equipped villa in Davenport

2–9 Sep

€ 141 per night

Guest favourite

Guest suite in Kissimmee

4.83 out of 5 average rating, 513 reviews

Private 2 bedroom w/bathrm in portion of POOL home

8–15 Aug

€ 85 per night

Guest favourite

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

30 Oct – 6 Nov

€ 140 per night

Home in Davenport

4.86 out of 5 average rating, 205 reviews

Disney World Area Villa Orlando * Pool * Sleeps 10

29 Jan – 5 Feb

€ 183 per night

Guest favourite

Home in Davenport

4.9 out of 5 average rating, 200 reviews

Disney Area Luxury Villa with Private Pool

22–29 Aug

€ 170 per night

Guest favourite

Apartment in Kissimmee

4.92 out of 5 average rating, 264 reviews

Beautiful Beach Style Condo minutes from Disney

15–22 Nov

€ 139 per night

Guest favourite

Cottage in Kissimmee

4.94 out of 5 average rating, 372 reviews

Entire Cottage close to Disney, Universal, Airport

19–26 Jul

€ 123 per night

Home in Kissimmee

4.79 out of 5 average rating, 257 reviews

3 bedroom Orlando Florida pool home

12–19 Jan

€ 136 per night

Quick stats about holiday 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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