Kid-friendly vacation rentals in Winter Haven

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Winter Haven

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

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Guest favorite

Guesthouse in Winter Haven

4.95 out of 5 average rating, 202 reviews

The Paradise Hide Away

This is a beautiful and private place newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! Talk to me if you need different check in/out times? Dogs are allowed with permission. There is a $200 fully refundable pet security deposit to cover any damages that may occur since Airbnb doesn’t cover damages caused by pets plus a non refundable pet fee of $50 per pet for every 1-7 day period and must be paid before checking in !

Dec 27 – Jan 3

G$16,442 GYD per night

Guest favorite

Guesthouse in Lake Alfred

4.95 out of 5 average rating, 119 reviews

Adorable Agave Suite w/ private pool and entrance

Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private back entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.

Aug 23 – 30

G$18,628 GYD per night

Guest favorite

Villa in Lake Wales

4.99 out of 5 average rating, 179 reviews

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

Nov 6 – 13

G$31,984 GYD per night

Guest favorite

Apartment in Winter Haven

4.99 out of 5 average rating, 137 reviews

STAR WARS Galaxy WORLD near LEGO land/Disney World

In a land far far away here it is Star Wars Galaxy world apartment. 6 months in the making. If you love Star Wars you will be amazed and thrilled. Two balconies included one overlooking lake and one looking over Garys world museum. Play a game of pool .. Full kitchen with washer dryer included. All the modern technology included laptop. Blue tooth. Charging stations and wireless charging. All Star Wars movies,music, Xbox available. 13 minutes from Legoland,45 min. Disney and universal studios

May 4 – 11

G$28,990 GYD per night

Guest favorite

Apartment in Auburndale

4.95 out of 5 average rating, 214 reviews

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

Jun 3 – 10

G$17,648 GYD per night

Superhost

Guesthouse in Winter Haven

4.87 out of 5 average rating, 232 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

Aug 14 – 21

G$14,944 GYD per night

Guest favorite

Guesthouse in Lake Hamilton

4.9 out of 5 average rating, 143 reviews

Luxury Cottage Near Legoland & Chain of Lakes

The Old Florida Cottage, in the quaint community of Lake Hamilton, just 5-miles from Legoland, less than an hour from Disney, and minutes away from the only public boat access to Lake Hamilton, is your perfect getaway! Enjoy a fully-equipped kitchen, a luxurious suite and modern bathroom, surrounded by Old Florida decor. We look forward to welcoming you to the cottage, with its own entrance and dedicated parking, located on a quiet street. Your home away from home!

Sep 15 – 22

G$28,198 GYD per night

Guest favorite

Home in Winter Haven

4.94 out of 5 average rating, 144 reviews

Cozy Family Home Near Legoland

Relax with the fam after a fun day at LEGOLAND (4.1 miles) or Disney World (36 miles) in our cozy home complete with a well-stocked kitchen, fully-fenced backyard, and comfortable beds. Spend a day on the famous Chain of Lakes (24 canal-connected lakes), catch a free ski show on Lake Silver, wander downtown to shop, or toast a pint at Union Taproom. Winter Haven is centrally located between Tampa and Orlando with plenty of fun nearby for the whole family.

Mar 30 – Apr 6

G$27,276 GYD per night

Guest favorite

Guest suite in Winter Haven

4.91 out of 5 average rating, 140 reviews

2 Bedroom Winter Haven Guest Suite

Private lock-off unit. Only shared between your party. 1st bedroom -Queen bed and sitting area bathroom attached. 2nd bedroom- two twin sized beds Kitchen and living room included and not shared outside of your party. 3 minutes from Winter Haven hospital. Self check in and out. 20 minutes from Legoland. 45 minutes from Disney and Universal This is an older florida neighborhood with a diverse and working class vibe. Located on Lake Maude

Sep 26 – Oct 3

G$21,165 GYD per night

Guest favorite

Guesthouse in Auburndale

4.97 out of 5 average rating, 193 reviews

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Aug 17 – 24

G$13,546 GYD per night

Guest favorite

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)

Nov 16 – 23

G$23,860 GYD per night

Superhost

Home in Winter Haven

4.86 out of 5 average rating, 110 reviews

The Flamingo

The Flamingo has been completely refreshed with paint, flooring, beds, furniture and many kitchen amenities. It is located 5 miles from Legoland, 30 miles to Disney World, near great restaurants, lakes, downtown Winter Haven and various shopping and attractions.

Jul 16 – 23

G$20,392 GYD per night