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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.

8–15 Aug

₹12,576 per night

Guest favourite

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.

4–11 Nov

₹14,076 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!

27 Sep – 4 Oct

₹7,256 per night

Guest favourite

Apartment in Davenport

4.97 out of 5 average rating, 152 reviews

Disney Orlando Bahama Bay Resort Theme Parks &More

1st floor Caribbean style condo with fully equipped kitchen, eating area, living room, 3 bedrooms, and 2 full bathrooms. The unit has everything you need including linens, towels & kitchen items. Resort amenities include pools, hot tubs, kids splash pad, tennis court, basketball court, lake, beach area, walking trails and more. We're located near Walt Disney World theme parks, Universal, SeaWorld, restaurants, entertainment and all that Orlando has to offer. Please add us to your WISH LIST.

30 Nov – 7 Dec

₹10,191 per night

Guest favourite

Cottage in Lake Wales

4.88 out of 5 average rating, 108 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.

10–17 Mar

₹11,156 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

7–14 Feb

₹12,800 per night

Guest favourite

Home in Clermont

4.93 out of 5 average rating, 188 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow full disinfecting of the house.

10–17 Jul

₹14,605 per night

Guest favourite

Apartment 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.

9–16 Nov

₹11,301 per night

Guest favourite

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.

7–14 Jul

₹6,436 per night

Guest favourite

Cottage in Kissimmee

4.96 out of 5 average rating, 421 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.

17–24 Sep

₹8,416 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).

2–9 Jan

₹32,251 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!

28 Jul – 4 Aug

₹9,431 per night

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Popular amenities for Winter Haven family-friendly rentals

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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

30 Sep – 7 Oct

₹11,250 per night

Guest favourite

Apartment in Champions Gate

4.85 out of 5 average rating, 262 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

8–15 Oct

₹11,024 per night

Guest favourite

Apartment in Orlando

4.97 out of 5 average rating, 297 reviews

Luxurious Waterfront Resort near Disney &Universal

29 Aug – 5 Sep

₹14,787 per night

Guest favourite

Apartment in Orlando

4.91 out of 5 average rating, 407 reviews

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

19–26 Oct

₹9,305 per night

Guest favourite

Apartment in Kissimmee

4.84 out of 5 average rating, 250 reviews

Lake View Family Condo Disney Universal Orlando

1–8 Oct

₹9,756 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

₹17,648 per night

Guest favourite

Townhouse in Kissimmee

4.97 out of 5 average rating, 280 reviews

Find a Little Magic in a Townhouse near Disney and Universal

14–21 Dec

₹15,629 per night

Guest favourite

Townhouse in Davenport

4.92 out of 5 average rating, 202 reviews

Disney Villa at Regal Palms*Near Pool/Lazy River

20–27 Nov

₹15,757 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

11–18 Nov

₹20,056 per night

Guest favourite

Townhouse in Kissimmee

4.92 out of 5 average rating, 227 reviews

Beautiful Farm House Decor near Disney, Sleeps 6

18–23 Sep

₹8,693 per night

Guest favourite

Home in Lakeland

4.91 out of 5 average rating, 121 reviews

Central Lakeland Home Convenient to Parks & Sports

10–17 Sep

₹15,844 per night

Guest favourite

Villa in Kissimmee

4.78 out of 5 average rating, 406 reviews

7BD with Movie Theater Pool & Jacuzzi near Disney!

5–12 Dec

₹27,260 per night

Guest favourite

Home in Kissimmee

4.89 out of 5 average rating, 176 reviews

PrivateJacuzzi-BBQ-ResortPool-Gym-7mlsDisney

31 Oct – 7 Nov

₹12,683 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

4–11 Jul

₹9,812 per night

Guest favourite

Villa in Davenport

4.9 out of 5 average rating, 170 reviews

Beautiful villa home near Disney

27 Nov – 4 Dec

₹23,478 per night

Guest favourite

Villa in Kissimmee

4.85 out of 5 average rating, 370 reviews

Amazing Cozy 4Bed/3Bath, Disney Area, Private Pool

17–24 Jan

₹16,399 per night

Family-friendly home rentals with a pool

Home in Davenport

4.86 out of 5 average rating, 205 reviews

Disney World Area Villa Orlando * Pool * Sleeps 10

9–16 Sep

₹13,067 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

17–24 Jan

₹5,757 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

₹12,391 per night

Guest favourite

Cottage in Kissimmee

4.94 out of 5 average rating, 371 reviews

Entire Cottage close to Disney, Universal, Airport

30 Jul – 6 Aug

₹8,248 per night

Guest favourite

Apartment in Kissimmee

4.92 out of 5 average rating, 264 reviews

Beautiful Beach Style Condo minutes from Disney

21–28 Oct

₹8,980 per night

Guest favourite

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

21–28 Apr

₹10,232 per night

Guest favourite

Home in Davenport

4.81 out of 5 average rating, 131 reviews

Welcoming fully equipped villa in Davenport

9–16 Jan

₹11,927 per night

Home in Davenport

4.92 out of 5 average rating, 241 reviews

Orlando Disney area home

7–14 Sep

₹12,678 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
7.7T reviews

Destinations to explore