Family-friendly holiday rentals in Haines City

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.

4.94 out of 5 average rating, 186 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, 136 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.

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.

4.89 out of 5 average rating, 121 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, arcade and gym (extra fee), soccer & football field, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

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, 269 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, 157 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.

Guest house in Auburndale

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.

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.

4.94 out of 5 average rating, 110 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, 204 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!

Apartment in Four Corners

The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.

4.87 out of 5 average rating, 166 reviews

"Ocean's Gate" - 2BD/2BA condo near Disney

Welcome to our beautiful ground-level condo! With the prime location at ChampionsGate Resort near Disney World and major parks, this 2BD/2BA condo unit is designed for your best accommodation. Spread out in 1,558 Sq. Ft., the unit offers a fully equipped kitchen, a cozy living room, a working station, and comfortable bedrooms. With access to the Clubhouse and resort amenities, you’ll spend amazing days in our home!

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.

4.82 out of 5 average rating, 146 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.

4.89 out of 5 average rating, 141 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.

4.89 out of 5 average rating, 138 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, 137 reviews

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

Villa in Kissimmee

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

4.93 out of 5 average rating, 162 reviews

A private pool area with a raised hot tub is enclosed by a screen, offering safety and quality views of the surroundings. The pool is accented by textured stonework and features a basketball hoop. A vibrant sunset casts colorful hues across the sky.

Villa in Davenport

Private Villa near Disney & Universal W/Pool & Spa

4.99 out of 5 average rating, 138 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, 136 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!

4.98 out of 5 average rating, 124 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

Magical 5BR Family Vacation Villa

An aerial view of the resort reveals a sprawling water park, featuring winding lazy rivers and multiple pools surrounded by lush palm trees. Access to sports courts and landscaped areas can be seen, offering a vibrant atmosphere for leisure activities.

4.95 out of 5 average rating, 121 reviews

Lazy River, Pool, Slide, Cafe / 4 Bedroom Villa

Villa in Championsgate Village

A vibrant game room displays an air hockey table and foosball station, with colorful LED lights casting an engaging glow. An adjoining indoor theater features plush seating and a large screen, while a private pool area invites relaxation, surrounded by lush greenery and floatation devices.

4.97 out of 5 average rating, 102 reviews

Pool Movies|Water Park|Movie Theater|Arcade|Themed

5 out of 5 average rating, 99 reviews

The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.

Home in Four Corners

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 113 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

4.96 out of 5 average rating, 51 reviews

A modern townhouse is pictured within a gated community. The exterior features a tiled roof and multiple balconies, complemented by landscaped gardens. Paved walkways lead to the entrances, while surrounding greenery offers a serene backdrop.

Townhouse in Haines City

Modern townhouse Balmoral Resort

4.96 out of 5 average rating, 156 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

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, 169 reviews

Modern Southern Dunes Pool House on Golf Course

Campervan/Motorhome in Lake Wales

A wooden barrel sauna is situated in a serene garden space surrounded by bamboo. The sauna features two benches and a wooden door, with soft lighting highlighting its natural texture and the tranquil atmosphere of the area.

4.85 out of 5 average rating, 102 reviews

Bamboo Bus -Sauna/ Pool/Fire pit/Grill

The image presents a collage featuring a private pool area with a screened enclosure under a blue sky, a cozy bedroom with green accents and a whimsical theme, and an elegant living space with modern furnishings. Natural light brightens each area, showcasing inviting design elements.

4.95 out of 5 average rating, 111 reviews

Great Location | Heated Pool | Awesome Design

Place to stay in Davenport

A modern dining area features a white marble island surrounded by wooden chairs. The room is accented by a floral wallpaper and a decorative mirror. Natural light streams in through the window, illuminating the cozy seating area with a dark sofa and decorative pillows.

4.86 out of 5 average rating, 116 reviews

2 BM/French Country Style DPLX

4.94 out of 5 average rating, 102 reviews

A creatively themed bedroom features dark walls adorned with a Halloween motif. A spacious bed with vivid bedding is complemented by decorative lamps. The room includes a wall mural depicting a moonlit scene and a festive Christmas tree, enhancing its playful atmosphere.

Townhouse in Davenport

LazyRiver+NearDisney+Arcade+Water Park+HotTub

Family-friendly home rentals with a pool

5 out of 5 average rating, 4 reviews

Family Pool Home w/ Game Room & Themes

5 out of 5 average rating, 44 reviews

5bd Villa Eman Private Pool/Hot Tub close2Legoland

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 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, 55 reviews

La Casita in Kokomo Bay

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.

4.95 out of 5 average rating, 80 reviews

Southern Dunes Lakeview Poolhome

A vintage-style clock is mounted on the wall, featuring the iconic 'Platform 9¾' sign with a green light illuminating its face. The clock's circular frame is accented by a black metal bracket, adding a whimsical touch to the room's decor.

4.95 out of 5 average rating, 65 reviews

Harry Potter's 6bd 6.5ba Hogwarts Experience

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.

4.96 out of 5 average rating, 139 reviews

DisneyWorld 15min!Themed 4 BD home w/private pool!