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Family-friendly holiday 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.

28 Oct – 4 Nov

$200 SGD 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.

25 Nov – 2 Dec

$256 SGD 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!

26 Oct – 2 Nov

$116 SGD 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.

24 Nov – 1 Dec

$163 SGD 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.

24 Jun – 1 Jul

$178 SGD 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

16–23 Apr

$209 SGD 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.

16–23 Apr

$233 SGD 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.

10–17 Dec

$181 SGD per night

Guest favourite

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.

4–11 Dec

$113 SGD 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.

18–25 Nov

$95 SGD per night

Guest favourite

Townhouse in Kissimmee

4.92 out of 5 average rating, 226 reviews

Beautiful Farm House Decor near Disney, Sleeps 6

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

18–23 Sep

$142 SGD 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).

23–30 Apr

$523 SGD per night

Holiday rentals for every style

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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

3–10 Aug

$180 SGD per night

Guest favourite

Apartment in Champions Gate

4.85 out of 5 average rating, 262 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

10–17 Aug

$158 SGD 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

28 May – 4 Jun

$228 SGD per night

Guest favourite

Apartment in Orlando

4.97 out of 5 average rating, 296 reviews

Luxurious Waterfront Resort near Disney &Universal

24 Sep – 1 Oct

$236 SGD per night

Guest favourite

Apartment in Kissimmee

4.84 out of 5 average rating, 249 reviews

Lake View Family Condo Disney Universal Orlando

3–10 Sep

$156 SGD per night

Guest favourite

Home in Davenport

4.94 out of 5 average rating, 171 reviews

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

10–17 Jan

$282 SGD per night

Guest favourite

Townhouse in Kissimmee

4.95 out of 5 average rating, 251 reviews

Disney/Universal Home Away from Home!

30 Aug – 6 Sep

$209 SGD per night

Guest favourite

Serviced apartment in Davenport

4.83 out of 5 average rating, 120 reviews

Penthouse 3 beds Bahama Bay resort

11–18 Nov

$222 SGD 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

28 Aug – 4 Sep

$320 SGD per night

Guest favourite

Guest house in Windermere

4.94 out of 5 average rating, 239 reviews

Small Guesthouse near Orlando's Theme Parks

21–28 Mar

$183 SGD per night

Guest favourite

Home in Lakeland

4.91 out of 5 average rating, 121 reviews

Central Lakeland Home Convenient to Parks & Sports

4–11 Nov

$253 SGD per night

Guest favourite

Home in Orlando

4.85 out of 5 average rating, 124 reviews

The Prince House w/Free Parking (Central Location)

21–28 Jul

$204 SGD 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

$435 SGD per night

Guest favourite

Home in Kissimmee

4.89 out of 5 average rating, 176 reviews

PrivateJacuzzi-BBQ-ResortPool-Gym-7mlsDisney

4–11 Sep

$203 SGD 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

7–14 Apr

$158 SGD per night

Guest favourite

Home in Clermont

4.86 out of 5 average rating, 117 reviews

Cozy Family Home near Disney

29 Jul – 5 Aug

$188 SGD 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

15–22 Jan

$190 SGD per night

Guest favourite

Guest suite in Kissimmee

4.83 out of 5 average rating, 509 reviews

Private 2 bedroom w/bathrm in portion of POOL home

16–23 Jan

$92 SGD 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

$195 SGD per night

Guest favourite

Cottage in Kissimmee

4.96 out of 5 average rating, 421 reviews

Bright & Cozy Cottage Near Disney

28 Feb – 7 Mar

$162 SGD 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

$209 SGD per night

Guest favourite

Home in Davenport

4.87 out of 5 average rating, 109 reviews

Sandy Ridge Villa, Large South Facing Pool & Spa

19–26 May

$214 SGD per night

Home in Davenport

4.92 out of 5 average rating, 241 reviews

Orlando Disney area home

11–18 Dec

$194 SGD per night

Home in Davenport

4.79 out of 5 average rating, 102 reviews

Mintra’s Villa Pool & Spa

20–27 Apr

$197 SGD 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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