Family-friendly holiday rentals in Bartow

4.99 out of 5 average rating, 181 reviews

The charming yellow cottage is framed by a white picket fence, featuring a porch with two rocking chairs. The entrance is marked by a light blue door, with windows reflecting a bright and cheerful ambiance. Lush greenery and flowers create a welcoming landscape.

Cottage in Homeland

Garden Cottage at The Garden Gate Bed & Breakfast

At the Garden Gate, a fully licensed and professional bed and breakfast, we hope you will find respite; a quiet place to rest, relax and reconnect. The 1905 Garden Cottage, carefully restored and beautifully appointed, will be your home while you are here. Enjoy the view of the cottage garden and its seasonal vegetables and flowers from your front porch rocking chair. Fresh baked cookies and chocolates will greet you upon arrival and you will enjoy a full gourmet breakfast in the morning.

Guest suite in Winter Haven

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.

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. The dock has plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door. Please note there is no barrier around pool and all children (anyone under age of 18)must be supervised at all times. Guests must swim at their own risk. You may see horses in the paddocks. The pool deck overlooks the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

4.95 out of 5 average rating, 314 reviews

The exterior of the home features a sleek black façade with large windows allowing natural light in. A neatly landscaped yard includes tropical plants and colorful foliage, enhancing the inviting entrance. The driveway leads to a single-car garage, with ample space to welcome guests.

4.99 out of 5 average rating, 147 reviews

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Just 6 miles to Legoland! This stylish home is perfect for vacation. 2 ensuite bedrooms, 2 additional rooms and 2 additional semi private sleeping areas there is room for everyone. Every space is newly furnished with stylish pieces and comfortable beds. The pool area is fully screened so you can enjoy the Florida weather without the bugs. The open concept space is perfect for large groups and families and the kitchen is ready for you to make a meal. A laundry room houses a washer and dryer.

Superhost

A living area features a beige sofa adorned with decorative pillows, positioned across from a wooden dresser and a flat-screen television. A geometric area rug is placed on the light wood flooring, while a soft light enters through sheer curtains covering a window.

Guest house in Bartow

Simple Apartment in quiet suburb

This property is about 1 hour from Tampa & Orlando, away from traffic and noise. This 1 bedroom apartment offers a comfortable bed with simple amenities. We are not far from many attractions such as Disney, Universal Studios, LegoLand, Busch Gardens, Seaworld, and more. The property has its own private entrance to come and go as you wish. Pickelball are courts nearby as well as grocery stores, local coffee shops, and local restaurants - all within 5 min. driving distance of the property.

4.78 out of 5 average rating, 144 reviews

A large outdoor space features a private pool surrounded by loungers in blue and a shaded dining area. A patio table with chairs is placed in the foreground, while a safety fence encloses the pool area, providing a secure environment.

4.98 out of 5 average rating, 123 reviews

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

Tiny home in Winter Haven

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 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.

4.92 out of 5 average rating, 162 reviews

4.99 out of 5 average rating, 310 reviews

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

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!

An outdoor dining area is shown under a shaded pergola, featuring a large table surrounded by comfortable chairs. The spacious pool is visible in the background, with a patio area adorned with colorful tiles. Lush greenery frames the scene, adding a tranquil vibe.

4.95 out of 5 average rating, 107 reviews

4/2 House near Legoland w Optional Heated Pool

Relax with the whole family at this peaceful home in Winter Haven 5mins to Legoland and the new Peppa Pig theme park, perfect for your next family vacation! Right across the street from lake Ned park with lake View from the front porch and office, bring your small water toys as there is a public boat ramp across the street. There are many restaurants as well as a Publix grocery store all within 2 miles from the home! Downtown winter haven is a short 10 minute commute.

An inviting swimming pool is surrounded by a spacious patio area, featuring lounge chairs and a shaded table with an umbrella. The serene view of Little Lake Otis and lush greenery is visible in the background under a partly cloudy sky.

4.91 out of 5 average rating, 222 reviews

Legoland Lakehouse Canoe & Kayak Retreat

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

A charming lake home is showcased with a light-coloured façade and blue shutters. A welcoming entrance is flanked by decorative chairs, with well-maintained landscaping featuring green grass and flower beds enhancing the outdoor appeal.

4.98 out of 5 average rating, 124 reviews

Lake View, Game Room, 10 min Legoland

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby!

A private backyard features a clean in-ground pool surrounded by a paved patio. Two lounge chairs are positioned beside the pool, and a dining set with four chairs sits nearby. Lush greenery and a white privacy fence enhance the serene outdoor setting.

4.97 out of 5 average rating, 148 reviews

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 11 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

Tiny home in Cypress Gardens

The exterior of the tiny house is showcased, featuring a welcoming front porch with steps leading up. Landscaping includes vibrant tropical plants and a stone pathway. The structure is set against a clear blue sky, highlighting the charming design and inviting ambiance.

4 a Tiny House w/ Bunk Bed in Quiet Marina Unit 14

Our cozy tiny house is perfect for when less is more :-). An intimate space for a long reflective weekend or a more affordable option for a few days with the kids at nearby Legoland. Offering a queen-size Murphy bed and two additional single-size bunk beds, the Cypress Inlet Tiny House can comfortably accommodate up to four people. Equipped with a mini-fridge, a microwave, and a Keurig duo (drip & pod) coffee maker.

4.86 out of 5 average rating, 176 reviews

Popular amenities for Bartow family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A cozy living area features a light brown sectional sofa and a matching sofa adorned with patterned cushions. A modern coffee table sits in the center, with a remote control placed on top. A large artwork of a character hangs above, flanked by two lamps.

4.89 out of 5 average rating, 137 reviews

Legoland Splash Escape (pool and hotub)

4.95 out of 5 average rating, 171 reviews

A spacious lawn is framed by large oak trees draped with Spanish moss. Comfortable lounge chairs are positioned facing the tranquil water, creating a serene outdoor space. The lake is visible in the background, enhancing the natural beauty of the setting.

Home in Auburndale

Lake Whistler Beach House with lakefront pool

4.98 out of 5 average rating, 133 reviews

Adult-Only Retreat w/ Pool & Spa | 18+, Private

4.99 out of 5 average rating, 158 reviews

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

Charming Tiny House on 5 acres with POOL/ HOT TUB

4.97 out of 5 average rating, 144 reviews

Home in Davenport

Magical 2 pool-Spa & Game Room Villa near “Disney”

4.96 out of 5 average rating, 102 reviews

A screened-in pool area features a clear, inviting swimming pool surrounded by comfortable lounge chairs. A basketball hoop is positioned at one end of the pool, with a scenic view of the lake and trees visible through the enclosure.

Home in Haines City

Southern Dunes Lakeview Poolhome

Guest house in Winter Haven

The living area features a dark brown couch adorned with orange throw pillows, positioned near a small wooden table. A vibrant yellow door and light green cabinetry add a cheerful touch. A rug with floral patterns is laid on the floor, creating a cozy atmosphere.

Cozy guest house w/ fenced yard and hot tub

4.8 out of 5 average rating, 130 reviews

4.96 out of 5 average rating, 116 reviews

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 291 reviews

A cozy living area features a dark futon sofa adorned with striped cushions, a wooden dining table with stationery, and a small kitchenette equipped with essential appliances. A partial divider provides privacy to the sleeping area, which contains a full-sized bed, contributing to the space's functional design.

Flat in Lakeland

Karen's Cottage

4.94 out of 5 average rating, 213 reviews

Guest house in Lakeland

Swan City Studio +Courtyard, mins historic downtwn

A spacious living area features a sectional sofa with an ottoman and two accent chairs, set on a soft, light rug. A ceiling fan provides cooling, while natural light filters through a large window dressed with sheer curtains. A small side table with a lamp complements the decor.

4.82 out of 5 average rating, 130 reviews

Heart of South Lakeland in adorable neighborhood!

A serene backyard features a clear swimming pool surrounded by a tiled deck. Sun loungers are positioned around the pool, with a shaded dining area beneath a striped umbrella. Lush greenery and tall trees provide a natural backdrop, enhancing the outdoor space.

4.79 out of 5 average rating, 350 reviews

Florida Oasis w/ Pool near LEGOLAND

Superhost

A small outdoor seating area is presented with a black round table and two folding chairs, situated on a green lawn area. A door adorned with a floral wreath provides access to the suite. Surrounding plants add greenery to the tranquil space.

Guest suite in Lakeland

Private Studio Suite

4.85 out of 5 average rating, 184 reviews

5.0 out of 5 average rating, 109 reviews

A welcoming porch features a swing adorned with cushions and a decorative pillow. A vibrant area rug lies underfoot, featuring intricate patterns in hues of blue and coral. Lush greenery and ornamental pumpkins enhance the inviting atmosphere, complemented by a small sign stating 'thankful.'

Cottage in Lakeland

Dixieland Delight

A serene lakeside view showcases the tranquil waters of Lake Hollingsworth, surrounded by lush greenery and walking paths. Patterns of vegetation are visible along the shoreline, while distant trees line the horizon, creating a peaceful natural landscape.

4.98 out of 5 average rating, 113 reviews

Lakeland LakeFront 4BD | 3BA FSC SEU Sun & Fun Tigers

4.94 out of 5 average rating, 190 reviews

Cute, Historic District Home - GREAT LOCATION

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 119 reviews

A bedroom showcases a leafy green accent wall, complemented by a light wood bed frame. Natural wood flooring adds warmth to the space. The bathroom features a modern vanity with dual sinks and a potted plant, while the outdoor area reveals a pool surrounded by a screened enclosure, illuminated by soft blue lighting.

Guest suite in Lakeland

Casa Planta Cozy Tropical Oasis Pool View Suite

Superhost

A serene lakefront scene captures a sparkling pool surrounded by palm trees at sunset. The sky features vibrant hues of orange and purple, reflecting in the calm water. Two lounge chairs are positioned beside the pool, creating a peaceful retreat.

Guest house in Winter Haven

The Russell Lake House

4.87 out of 5 average rating, 285 reviews

5.0 out of 5 average rating, 49 reviews

Home in Bartow

Dottie's Place, Comfy Home, Private Pool, BIG Yard

4.93 out of 5 average rating, 30 reviews

3/2 Beautiful Pool Home + Garage + Pet Friendly

The saltwater heated pool is enclosed within a screen patio, surrounded by a well-maintained white fence. Comfortable cushioned seating is visible nearby, along with potted plants adding a touch of greenery. Clear blue skies enhance the peaceful atmosphere of the outdoor space.

4.85 out of 5 average rating, 39 reviews

Relax in Heated Saltwater Pool w/ Screened Lanai

A modern lakefront home is showcased with a clean, spacious facade. Well-maintained landscaping features palm and leafy plants, complementing the beige exterior. A curved driveway leads to a two-car garage, with panoramic views of the lake apparent beyond the property.

5.0 out of 5 average rating, 42 reviews

Winter Haven Waterfront Retreat

5.0 out of 5 average rating, 49 reviews

Family Heated Pool Home Sleep 12 Near Tampa Disney

A rectangular pool is framed by a stone patio, featuring steps leading into the clear water. Sunlight creates gentle ripples on the surface, while the surrounding screened enclosure offers a view of the lush greenery beyond.