Family-friendly holiday rentals in Haines City

Townhouse in Four Corners

4.96 out of 5 average rating, 166 reviews

Near Disney/Baby Friendly/Water Park/Mini-Golf/Gym

Welcome to your stylish, themed vacation home in one of the most popular resort communities in the Four Corners/Championsgate area just 15 minutes away from Disney World and close to other local theme parks. The home is crafted with love for your enjoyment & comfort. This beautiful townhome has 3 bedrooms, 2.5 bathrooms, all new furniture, and super fast 1 Gbps internet speed. You will have free access to a large beach-entry pool, kids water park, beach volleyball, mini-golf, restaurant & gym.

The two-story home is illuminated under a night sky, featuring clear glass windows that reflect soft light. Landscaped greenery surrounds the property, with a stone driveway leading to a garage. A large patio area is visible on the right side.

4.9 out of 5 average rating, 120 reviews

Breathtaking Home

New two story home with private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities located right across the street with an amazing clubhouse (private owned), Bar & Grill restaurant, water park (extra fee), arcade, gym, volleyball court, soccer & football fields, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

The exterior of the home features a light-colored facade with a welcoming entrance. A neatly landscaped yard includes vibrant green shrubs and a palm tree. The driveway leads to a single-car garage with a white door, set against a backdrop of clear blue skies.

4.9 out of 5 average rating, 183 reviews

Southern Dunes Villa - Pool - Golf - near Disney

Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. Only 13 miles from LEGOLAND and 22 miles from WALT DISNEY WORLD, this is the perfect place to relax after a busy day at the parks. Impeccably maintained, our villa features upgraded furniture, electronics, mattresses and flooring. Southern Dunes is a gated golf community that prides itself on the quality of its golf course and the security and beauty of its homes.

Guest house in Lake Alfred

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.

4.93 out of 5 average rating, 183 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.

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.

4.92 out of 5 average rating, 132 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.

Guest house in Lake Hamilton

A bright bedroom features a spacious bed with white linens and decorative pillows. Light-colored walls are complemented by a ceiling fan. Natural light enters through a nearby window, and simple decor adds a relaxed feel. A chair is placed beside the bed for added comfort.

4.89 out of 5 average rating, 265 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!

4.86 out of 5 average rating, 155 reviews

A well-maintained villa is showcased, featuring a welcoming entrance with a single-car garage. Lush greenery and colorful shrubs line the brick pathway, while tall palm trees and vibrant landscaping enhance the cheerful exterior. Bright clouds are visible in a clear blue sky.

Villa in Haines City

Sandy's Southern Dunes Villa

This villa is in the Southern Dunes Golf & Country Club, which is an immaculately kept, secure complex, which maintains a 24-hour manned gate, making this a safe place to stay. There are community swimming pools, tennis courts, a gym, library and children's playground for those days when meeting Mickey Mouse is just too much trouble. With a Super-Walmart a minute away plus Dicks and several well-known restaurants just further away, virtually everything is on hand.

4.94 out of 5 average rating, 108 reviews

A serene bedroom features a spacious bed with decorative pillows. A nightstand with a clock and a small plant is placed beside the bed. The wall showcases an art piece of leaves against a deep blue background, and sunlight filters through the window with white blinds.

Guest suite in Davenport

NEW Cozy 1 bedroom w/ living room close to Disney

Kick back and relax in this calm, stylish space. 2 people max. It has a seperate entrance through the garage. The property is a single family house with 2 units. The space is private, does not share space. Includes wifi, A/C and parking. 1BR w/ Queen Bed, 1 Bathroom with a tub, has washer/dryer installed and a cozy Living room with a 55 inch TV. A 25 min drive to DIsney World and 35 to Universal Orlando. A Walmart Supercenter 8min away. Gas station 3 min away.

4.92 out of 5 average rating, 202 reviews

A spacious bedroom is displayed, featuring a cozy bed adorned with neutral-toned bedding and green accents. Sliding wooden barn doors provide a modern touch, while natural light filters through partially curtained windows, highlighting the room's inviting atmosphere.

Cottage in Davenport

$69! Cozy Cottage + Outdoor Fun -Close to Disney!

Book with us now and receive access to all of these amenities✨: •Lightning Fast Internet ⚡️ •Outdoor Movie Theater 🎥 •Ping Ping Table/Pool Table 🏓🎱 •Complimentary Coffee & Breakfast ☕️ •Safe Gated Location •Large Enclosed Covered Patio •Comfortable Queen Sized Bed •Cable TV (Adjustable) •Modernized Brand New Full Bathroom •Nearby All Major Attractions •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •And Much More! Book with us now!

An aerial view presents the stylish exterior of KokomoVilla, showcasing a well-maintained garden and driveway. The property is bordered by lush greenery and overlooks the golf course, with a sunset casting a warm glow across the sky, enhancing the serene atmosphere of the neighborhood.

4.81 out of 5 average rating, 142 reviews

KokomoVilla Pool Home at Southern Dunes

Welcome to KokomoVilla at Southern Dunes! Our 4-bedroom pool home offers a serene golf course view in the renowned Southern Dunes Golf & Country Club. Perfectly positioned between Disney and Legoland, this luxurious retreat is ideal for families and golf lovers. Enjoy a fully equipped home, private pool, and easy access to Central Florida’s attractions. KokomoVilla is not just a stay, but an unforgettable experience!

Tiny home in Winter Haven

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.

4.88 out of 5 average rating, 137 reviews

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.

The exterior of the home features a fresh white brick façade with contrasting dark shutters on the windows. A circular driveway is lined with vibrant landscaping, including flowering plants and greenery. The property is well maintained, with a clear view of the entrance and a sunny blue sky overhead.

4.9 out of 5 average rating, 134 reviews

Villa Blanca

Relax with the whole family at this peaceful pool home located off the quiet roads along the higher elevation of the Florida ridge. Propane tank for home generator. In ground pool covered by enclosed screen. Property fronts the old Sun Air Golf course (not active). An active bar and grill still operates in the old country club at the end of the neighborhood. Right in the center of both Legoland and Disney World

Popular amenities for Haines City family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 135 reviews

A private pool area is illuminated in a soft green hue, surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, with a table set under an umbrella. String lights create a warm ambiance as the evening sky darkens.

Villa in Davenport

Magical Disney House-Pool & Hot Tub,Free Waterpark

4.86 out of 5 average rating, 286 reviews

A spacious swimming pool is surrounded by palm trees and landscaped gardens. Lounge chairs line the poolside, offering a place to relax. The resort's clubhouse is visible in the background, showcasing a welcoming design with large windows.

Flat in Davenport

Recently Award Winning Renovated 2+2 Near Disney

A bright and open living area features modern furnishings, including a sectional sofa and stylish yellow accent chairs. A large flat-screen TV is mounted on the wall, while decorative elements and a vibrant area rug contribute to the space's contemporary aesthetic.

4.9 out of 5 average rating, 150 reviews

Awesome Vacation Home w/ Private Heated Pool/Spa

4.99 out of 5 average rating, 127 reviews

The collage showcases various areas of the lakeside home. Highlights include a private patio dining set, a resort-style pool, a comfortable living space with a dining table, and vibrant bedrooms featuring bunk beds and colorful decor. The picturesque lake view complements the outdoor spaces.

Townhouse in Kissimmee

Lake View - 5 Miles to Disney!

A colorful bunk bed structure is featured, decorated in vibrant shades of yellow, blue, and orange. The mural backdrop depicts a jungle scene with a leopard and tropical plants, enhancing the playful atmosphere of the room. Spiral staircases offer access to the upper sleeping area.

4.95 out of 5 average rating, 105 reviews

Themed Home + Near Disney + Arcade + King Bed + Water Park + Spa

4.92 out of 5 average rating, 175 reviews

A Star Wars themed bedroom features two twin beds with themed bedding. A decorative quilt with a pattern of star fighters is placed over one bed, while the other is dressed in a space-themed cover. A bedside table holds a lamp shaped like a lightsaber, with blue walls adorned with framed artwork.

Apartment in Kissimmee

Themed Resort Condo | Pool | Spa | Mins to Disney

The vibrant water slide stands prominently beside a rock formation, flowing into a clear blue pool surrounded by tropical palm trees. Below, a spacious game room featuring foosball and air hockey tables is visible, alongside a view of the inviting pool area.

4.86 out of 5 average rating, 111 reviews

Whimsical 6BR Solterra Oasis - Themed Rooms & Pool

A vibrant game room features arcade machines themed around racing and superheroes. Adjacent, an outdoor space showcases a heated pool and hot tub, complemented by a fully equipped kitchen. The playful bedrooms are designed for immersive adventures inspired by Toy Story and Marvel.

4.99 out of 5 average rating, 137 reviews

Spectacular! Disney/Universal Themed Home

Family- and pet-friendly home rentals

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.

4.95 out of 5 average rating, 288 reviews

Horse Farm on a Beautiful Lake

4.95 out of 5 average rating, 277 reviews

The open studio layout features a spacious bed with patterned bedding, adjacent to a modern kitchen equipped with white cabinetry and appliances. A cozy blue sofa offers additional seating. Natural light filters through the window coverings, illuminating the wood-paneled ceiling and inviting atmosphere.

Cabin in Lake Alfred

The Lake Alfred Citrus Wood Guest Cabin

4.99 out of 5 average rating, 112 reviews

A charming white cottage is framed by a well-kept lawn, with a brick chimney visible on one side. Lush green shrubs and trees provide shade around the property, and a pathway leads to the entrance, suggesting easy access to the home.

Cottage in Davenport

Classic Cottage in country setting

A spacious living area features a large sectional sofa arranged around a round coffee table. Bright lights illuminate a modern kitchen equipped with white cabinetry and an island with seating. A ceiling fan is suspended above, enhancing the airy ambiance.

4.95 out of 5 average rating, 147 reviews

Stylish Stay in Davenport

Holiday home in Haines City

A private pool is set within a screened enclosure, providing a view of the surrounding greenery and golf course. Lounge chairs with blue cushions are positioned nearby, inviting relaxation. The pool water appears clear and inviting under the natural light filtering through the enclosure.

4.86 out of 5 average rating, 166 reviews

Modern Southern Dunes Pool House on Golf Course

A large outdoor pool is surrounded by palm trees and lounge areas. The water is clear, reflecting the sky and clouds above. Paved pathways border the pool, providing access to seating and sunbathing spots.

4.85 out of 5 average rating, 239 reviews

⭐⭐⭐⭐⭐ 20 MINUTES FROM DISNEY WORLD/UNIVERSAL PARK

An inviting outdoor space features a gently curving pool with a built-in hot tub, surrounded by a screened enclosure. Comfortable lounge chairs are arranged nearby, with two patterned hammocks and a dining area visible in the background. Soft evening colors fill the sky above.

4.78 out of 5 average rating, 119 reviews

There is no other place you want to be than here.

4.93 out of 5 average rating, 138 reviews

The exterior features a light blue structure complemented by a covered carport. A well-maintained lawn with decorative stones and shrubs adds to the inviting atmosphere. Large windows provide natural light into the living spaces.

Home in Kissimmee

Winter Villa in Florida by the Lakes

Family-friendly home rentals with a pool

An inviting pool area is captured with a winding swimming pool bordered by a concrete deck. Several lounge chairs are positioned around the pool, complemented by a dining table adorned with a small plant. Lush greenery surrounds the space, enhancing the outdoor setting.

4.98 out of 5 average rating, 46 reviews

Cozy, Relaxing & Fun Gateway!

A screened-in pool area features a heated pool, lounge chairs with colorful cushions, and an outdoor TV mounted on the wall. A small table with a book and a bottle is positioned nearby, creating a relaxed atmosphere for outdoor enjoyment and entertainment.

4.96 out of 5 average rating, 25 reviews

Private Heated Pool~Game Loft~Arcade~Near Disney

An expansive pool area is surrounded by lounge chairs and palm trees, featuring a large beach-entry pool sparkling under blue skies. Nearby, a vibrant kids' water play area features a large pirate ship structure. A spacious living area is designed with light furnishings and a large TV, while a children's bedroom showcases Disney-themed twin beds with playful decor.

4.99 out of 5 average rating, 112 reviews

3bd/2.5b Close to Disney °Luxury Paradise Living

A children's bedroom features a vibrant underwater theme, with blue walls and colorful murals depicting marine life. Bedding includes a twin-over-twin boat bunk bed and a separate twin bed. Decorative elements like shells and a net create a playful atmosphere, while curtain-filtered light adds a soft glow.

5 out of 5 average rating, 129 reviews

5 stars! waterpark! GameRm! Ariel Buzz StarWars

4.95 out of 5 average rating, 133 reviews

A spacious living area is presented with a sectional sofa, a wooden coffee table, and a wall-mounted television. Large windows allow natural light and views of the outdoor patio. The room features light-colored walls and art pieces that add a modern touch.

Home in Winter Haven

Legoland Getaway 7 mins • Sleeps 7 • Elevator

A single-story home is showcased, featuring a light-colored exterior and a neatly landscaped front yard. Lush palm trees and shrubs enhance the lush green lawn. A driveway leads to a garage, while clouds drift in a clear blue sky overhead.

5 out of 5 average rating, 50 reviews

La Casita in Kokomo Bay

4.98 out of 5 average rating, 121 reviews

The image showcases a vibrant collage of the villa's features. The top left displays a colorful Encanto-themed bedroom with a playful bed. The top right features the modern living area with large windows and comfortable seating. The bottom left presents a private pool area, and the bottom right highlights a Mario-themed game room with arcade games.

Villa in Davenport

5BR Family Vacation Villa w/Free Pool Heat