Family-friendly vacation rentals in Haines City

4.96 out of 5 average rating, 166 reviews

A modern kitchen is featured, showcasing white cabinetry and a marble countertop. The central island is equipped with a sink and offers additional workspace. Sleek stainless steel appliances are present, including a refrigerator and an oven, while pendant lights provide illumination.

Home in Four Corners

New Gtd community Sleeps 6 - 3B/2 bth near Disney

NEWLY BUILT private home. Enjoy a stylish experience with fully equipped kitchen and EVERYTHING brand new. Sleeps up to 6 in 3bed/2bath. Includes 1 KING and 4 Twin beds with a tv in each room. Enjoy the arcade game and lounge in the relaxing open space. Connect to WiFi and enjoy the dedicated workspace. Safe & secure smart house in gated community. Access to resort style pools, sports courts & more. Minutes from several entertainment spots including Disney, shopping & restaurants all close by.

Vacation 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

We invite you to Stay at our Updated 3 Bedroom Southern Dunes Pool home with a Golf View located in the award winning Southern Dunes Golf & Country Club. Of all Orlando golf courses in the Central Florida area, Southern Dunes may be the most unique. Located between Disney and Legoland, and Central Florida attractions. So whether it's the theme parks, golfing, beaches, shopping, water sports, fishing, relaxing or all of these, you'll find yourself perfectly placed for a great Florida vacation.

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.

Guesthouse 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.

The large beach-entry pool features a gentle sloping entrance, surrounded by lush palm trees and shaded umbrellas. Lounge chairs are positioned around the pool, offering a relaxing retreat. In the background, the resort's multi-story building demonstrates a blend of modern architecture and tropical landscaping.

5 out of 5 average rating, 108 reviews

Family-Fun Disney HQ w/Resort Pool, MiniGolf, Gym

Imagine vacationing a stone’s throw from all the Disney theme parks while staying at a resort that also caters to family entertainment! Family dreams come true at this new townhome, where you’ll find a fully equipped kitchen and everything you need for a comfortable stay. All this, plus access to the recreation and entertainment resort features, including large beach-entry pool, water/splash park, mini golf, gym, and volleyball court. See how many "Hidden Mickeys" you can find in the home!

A light-filled living area features a wall-mounted television displaying a vibrant scene. Two blue chairs are positioned around a wooden coffee table, which is topped with a small plant. Greenery adds a touch of nature, and a patterned rug enhances the space's comfort.

4.78 out of 5 average rating, 131 reviews

Stylish 3BR: Pool, Golf Views, Disney, Legoland

Welcome to your ultimate 3BR/2BA getaway—where every day feels like a highlight reel! 🏡💫 💦 Dive, splash, repeat in your private pool ⛳ Sip, savor & soak in those dreamy golf views 🎢 Disney, Universal & Legoland? Just minutes away! Perfect for family fun or golf-lover escapes, this stylish retreat brings modern vibes, a chef-ready kitchen 🍳, and oh-so-comfy chill zones 🛋️. ✨ Like a resort, but all yours! Book now & let the good times roll! 🌴🎉 🌟 Let the memories begin! 😎

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.

Guesthouse 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, 264 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.

4.92 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!

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.

4.89 out of 5 average rating, 133 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

4.94 out of 5 average rating, 101 reviews

A vibrant children's bedroom features a colorful slide leading into a themed bunk bed structure. The walls are decorated with whimsical designs, including playful characters and bright colors. A small ladder allows access to the upper sleeping area, enhancing the playful atmosphere.

Home in Kissimmee

Disney Experience w/Pool, Game Rm, "Magic" Portal

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

4.99 out of 5 average rating, 130 reviews

A vibrant hallway is adorned with deep blue walls, featuring golden stars and a playful Mickey Mouse theme. A picture of Mickey Mouse in a wizard hat is displayed on the wall, complementing the themed decor. A stylish side table is positioned against the wall.

Villa in Four Corners

Mickey Fantasia Family Friendly w/accessibility

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, 149 reviews

Awesome Vacation Home w/ Private Heated Pool/Spa

4.99 out of 5 average rating, 126 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!

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, 135 reviews

Spectacular! Disney/Universal Themed Home

4.96 out of 5 average rating, 126 reviews

Townhouse in Kissimmee

*EPIC Tube Slide Bunk*FREE Pool Heat*5mi to Disney

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

4.95 out of 5 average rating, 146 reviews

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.

Townhouse in Davenport

Stylish Stay in Davenport

4.86 out of 5 average rating, 424 reviews

A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

Villa in Kissimmee

OMG! Disney Area, Movie Theater, Game Room & Pool!

The cozy bedrooms feature vibrant themes, with wall art enhancing the decor. A refreshing pool is visible, showcasing clear, inviting water surrounded by a smooth deck. Soft natural light streams in, creating a tranquil atmosphere throughout the space.

5 out of 5 average rating, 12 reviews

Disney on the Dunes

A screened-in pool area features a vibrant pool surrounded by greenery. A comfortable seating arrangement is offered, alongside a grill for outdoor cooking. The pool floats in a sunny yellow design while golf course views are visible in the background.

4.93 out of 5 average rating, 29 reviews

Disney Golf Dreamhouse with Pool 20 min to Disney!

4.85 out of 5 average rating, 140 reviews

The entrance features wooden steps leading up to a covered porch, flanked by tropical foliage. Two chairs are positioned on the porch, offering a place to relax. The home’s exterior is painted in soft green, complemented by light-colored trim.

Cottage in Winter Haven

5 - Life's a Beach Retreat 1bed/1bath - Unit 13

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!

4.96 out of 5 average rating, 25 reviews

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.

Townhouse in Davenport

Private Heated Pool~Game Loft~Arcade~Near Disney

4.99 out of 5 average rating, 111 reviews

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.

Townhouse in Davenport

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

The single-story home features a welcoming entrance surrounded by lush green landscaping. A private pool is visible through a screened enclosure, furnished with blue lounge chairs. Nearby, an expansive view of the golf course highlights the area’s natural beauty, complemented by an inviting dining and living space indoors.

4.87 out of 5 average rating, 70 reviews

Quiet house with pool on a Top golf course

A two-story, tropical style home is showcased, featuring a vibrant exterior in warm shades. A Tesla is parked prominently in the driveway, with lush palm trees and greenery flanking the entrance. The garage is accessible, contributing to the property's inviting curb appeal.

4.95 out of 5 average rating, 78 reviews

Luxury Tropical Themed Villa With Lake View!

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.

4.97 out of 5 average rating, 74 reviews

Southern Dunes Lakeview Poolhome

A private swimming pool is surrounded by a screened lanai, offering views of the home and lounge chairs. Clear blue water reflects the sky, while protective fencing provides safety. The outdoor space is designed for relaxing and enjoying the warm Florida sun.

4.92 out of 5 average rating, 72 reviews

Heated Pool | Luxury Design | Disney | Golf Course

An outdoor space features a private pool surrounded by a well-maintained lawn. A children's playground structure is located nearby. Comfortable lounge chairs and a shaded seating area are available on the patio, offering a relaxing environment for outdoor enjoyment.