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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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Guest favorite
Guesthouse in Lakeland
4.95 out of 5 average rating, 193 reviews

Santa’s Studio+Cozy Courtyard, Firepit, near dwntn

Your cozy retreat awaits you in Swan City Studio! It is centrally located in Lakeland, a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) The studio comes fully equipped with everything you need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the well appointed modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Private parking is just a few steps down the pathway through the courtyard from your door!

Guest favorite
An inviting outdoor patio is presented, featuring comfortable seating on a woven couch and armchairs under a vibrant blue umbrella. Lush greenery and palm trees surround the area, adding to the tranquil ambiance, while a charming two-story building serves as a backdrop.
Guesthouse in South Lake Morton Historic District
4.89 out of 5 average rating, 186 reviews

Cozy patio level studio In Historic district

This cozy, Patio level studio is on our homes property, it has a KITCHENETTE, WITH LIMITED COOKING. It is nestled in the Historic District of Lakeland and mere steps from Florida Southern a Frank Lloyd Wright designed campus, a tour is recommended! Our cobblestone streets take you to unique neighborhood restaurants. We are walking distance of beautiful downtown Lakeland. We are between two lakes- Lake Hollingsworth, a great 3+ mile walking/running path and Lake Morton which is a bird paradise.

Top guest favorite
The Tiny House is situated in a serene outdoor setting, featuring a light-blue exterior with a metal roof. A wooden porch with rocking chairs extends at the front, while the surrounding landscape includes lush green grass and landscaping along a gravel path.
Tiny home in Lakeland
4.99 out of 5 average rating, 120 reviews

Charming Tiny House on 5 acres with POOL/ HOT TUB

Escape to the heart of Lakeland where our charming Tiny House awaits. Nestled on 5 acres of tranquility, you'll experience the best of both worlds: a peaceful retreat and easy access to local shopping centers just a stone's throw away. The Tiny House is furnished with a queen size bed and a king sized bed in the upstairs loft, kitchen, full bath as well as a designated work area. Take a refreshing dip in the shared pool, unwind in the hot tub, or simply soak up some sun on the lounge chairs.

Guest favorite
A screened-in pool area features a clear, inviting swimming pool with a light blue surface. Two striped lounge chairs are positioned beside the pool, and a small seating arrangement is visible in the background, providing a space for relaxation and outdoor enjoyment.
Guesthouse in Lake Alfred
4.93 out of 5 average rating, 184 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 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.

Top guest favorite
A wooden deck overlooks the calm waters of Lake Ariana, framed by greenery. A small table with two chairs is positioned to enjoy the view, while a potted plant adds a touch of nature to the space. Spanish moss drapes gracefully from nearby branches.
Apartment in Auburndale
4.95 out of 5 average rating, 244 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

Top guest favorite
The indoor area features colorful Lego-themed decor, including a bed covered with a vibrant quilt, and a comfortable sofa with bright cushions. A TV is mounted on the wall. A refrigerator and kitchen area are visible, with a game table and playful rug adding to the lively atmosphere.
Tiny home in Winter Haven
4.92 out of 5 average rating, 134 reviews

Tiny Lego Home

Tiny Lego home just 12 minutes from Legoland/Peppa pig. Everything to keep the kids entertained. Massive playground and dining/ grilling area, Large outdoor Lego building area, Indoors every thing Lego. Wall legos, table legos and more. If you like Legos this is the place to stay. The kids will be in Lego heaven! Recently added swimming pool with deck and soccer field in playground area. The outdoor playground park is a shared space for any guests who may be staying at complex.

Top guest favorite
A view of the blue lake house is presented with a well-manicured lawn leading up to it. The house is framed by mature trees, providing shade. A wooden walkway extends toward the entrance, while the serene lake is visible in the background.
Cottage in Eagle Lake
4.99 out of 5 average rating, 284 reviews

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

Top guest favorite
A serene pool area is enclosed by a protective screen, featuring a clear swimming pool surrounded by a tiled patio. A comfortable seating area is visible in the background, with a stylish egg chair. Lush greenery enhances the tranquil setting.
Guesthouse in Auburndale
4.97 out of 5 average rating, 245 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. The apartment is behind my personal home with no connecting doors. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Top guest favorite
A comfortable living space features a large sectional couch adorned with decorative pillows. A mirror and wall art enhance the ambiance. Natural light enters through the front door, and a dining table is situated nearby. A ceiling fan provides a refreshing atmosphere.
Guest suite in Winter Haven
4.9 out of 5 average rating, 106 reviews

Cute & Cozy in Winter Haven, Florida

The guesthouse Cute & Cozy is private yet adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location from Florida's amazing beaches, just under 2 hours east or west. Maybe an hour drive to Disney, SeaWorld and Universal (depends traffic)

Guest favorite
A spacious outdoor area includes a pool surrounded by a white deck. Seating options are available, featuring lounge chairs and tables. The two-story building provides multiple balconies, framed by lush greenery and palm trees, contributing to a serene environment.
Loft in Auburndale
4.93 out of 5 average rating, 234 reviews

2 Bedroom Apartment near Legoland and Disney

This Private Studio features 2 bedrooms, kitchenette with dining area, private bath, walk-in closet, own entrance and from the Main Studio bedroom a large Balcony with Spectacular lake views. The Kitchenette with dining table and the bathroom is located in between of the 2 Bedrooms. The second Bedroom is only 10'x10' with a Queen bed and Wardrobe. Early Check in or late check outs are not available

Guest favorite
The exterior of the home features a well-maintained facade with light blue siding and white trim. A spacious front porch is accessible by wooden steps, surrounded by landscaping with shrubs and small plants. Trees provide shade in the front yard.
Cottage in Winter Haven
4.9 out of 5 average rating, 148 reviews

3 - Lake Life House 1 bed/1bath - Unit 15

Whether you’re planning to try your hand at fishing in the region’s world-famous Chain of Lakes or scheming up a surprise family retreat to Legoland with the kiddos, this Winter Haven home is ideally located for your getaway! With 1 bedroom, 1 bathroom and access to a boat ramp on a private canal to Lake Eloise. This vacation rental makes it easy to experience the Florida lake life.

Top guest favorite
Three thoroughbred horses graze peacefully on a lush green pasture. The area is surrounded by tall trees, providing shade and a natural backdrop. A glimpse of a trailer can be seen in the background, indicating the farm's working environment.
Guest suite in Winter Haven
4.96 out of 5 average rating, 289 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)

Popular amenities for Winter Haven family-friendly rentals

When is the best time to visit Winter Haven?

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Avg. price€ 125€ 128€ 132€ 124€ 120€ 116€ 120€ 118€ 113€ 113€ 121€ 122
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Quick stats about vacation rentals that are family-friendly in Winter Haven

  • Total vacation rentals

    Explore 240 vacation rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 10,940 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 100 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    240 of Winter Haven vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Haven rentals

  • 4.9 Average rating

    Winter Haven stays are highly rated by guests—averaging 4.9 out of 5!

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