Family-friendly holiday rentals in Pine Castle

5 out of 5 average rating, 138 reviews

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.

Home in Davenport

All 5 star stay with Waterpark, GameRm, Ariel Buzz

★ WELCOME TO IMAGINATION STATION★ The SHORT bullet point version for busy parents - 5 bedrooms, 4 bathrooms - Ground floor is a Queen bed with a bathroom directly across the hall - Upstairs has 3 bedroom: One is master adult room with ensuite bathroom. The other 3 are kid rooms. StarWars have ensuite bath. Mermaid and Buzz share the hallyway bathroom - Stroller, crib, high chair, pack-n-play free for your use - About 5 houses down from club house (walkable) - Pool has safety fence and door al

A private heated pool is surrounded by a screened enclosure, featuring a brightly colored tiled edge. Sun loungers are positioned nearby, offering a relaxing space to unwind. A covered BBQ grill is accessible on the patio, creating an inviting setting for outdoor gatherings.

4.93 out of 5 average rating, 109 reviews

3BR / 2BR Heated Pool Home 7 Min to Disney |

✨ Experience comfort, style, and a private heated pool 💦 (optional) just 7 minutes from Disney World! This 3BR/2BA Kissimmee home is perfectly located near theme parks, shopping, and dining — and designed for families looking to unwind in a sparkling-clean, beautifully curated space. 📍Prime Kissimmee Location ⭐7 Min– Walt Disney World ⭐5 min–Orlando Premium Outlets ⭐15 min – Universal Studios, SeaWorld, Epic Universe 🎢 ⭐ 25 min – MCO Airport ✈️ ⭐ Walk to Walmart, Publix & Starbucks ☕️

Guest house in College Park

A charming exterior view of the studio garage apartment is shown, featuring a dark door adorned with a floral decoration. Stone steps lead up to the entry, surrounded by lush greenery and plants. The garage door is white with double panels, complementing the neutral wall color.

4.99 out of 5 average rating, 114 reviews

The Studio

Nestled off of a quiet brick street behind a 1922 bungalow, this studio garage apartment is a blend of cozy charm and convenience. Ideal for a solo traveler, but can accommodate two. The Studio has a private entry encompassing 3 rooms (bed/kitchen/bath). WiFi(200mbps); Roku TV, Netflix) provided. Quality grocery stores, restaurants, bars and lakes are a short walk away. Access to major highways are minutes away, making this location perfect for the business or leisure travel.

The living room area features a spacious sofa adorned with decorative orange pillows. A soft bucket chair sits adjacent. A dark coffee table holds a magazine and the remote control, while warm lighting is provided by a nearby lamp.

4.8 out of 5 average rating, 123 reviews

Cozy Home, Minutes from Airport & Near Everything

This centrally located house is priced low and ideal for long-term bookings. This cozy 1 bedroom, 1 bathroom, ground floor house is centrally located within 3 to 20 miles of all major attractions in Orlando. It has a big backyard (not fenced) with a small concrete patio with 2 chairs/small table. There is free parking for up to 2-3 cars in front of your entrance. It is within walking distance from some restaurants, shops, etc but a car is highly recommended.

4.87 out of 5 average rating, 230 reviews

A sparkling pool is surrounded by a paved patio, featuring several lounge chairs with blue cushions. Large umbrellas provide shade for relaxation. Lush greenery is visible in the background, enhancing the outdoor setting.

Home in Belle Isle

Year around Heated Pool 7 min from MCO Airport!

Welcome to Casa Linda Pool! This stylish 3BR, 2.5BA home sleeps 8 and features a private heated pool, fully equipped kitchen, open living space, and an amazing outdoor kitchen with BBQ grill, cooktop, and cooler for your drinks. Just minutes from Orlando Airport, Disney, and Universal. Perfect for families or groups looking to relax and enjoy Florida in comfort. Fast Wi-Fi, A/C, washer/dryer, and free parking included. Book now and enjoy your Orlando getaway!

4.99 out of 5 average rating, 152 reviews

A living area features a plush sofa and two armchairs arranged around a circular coffee table. Natural light filters through the window, illuminating the space. A vibrant area rug anchors the seating area, while a bouquet of flowers adds a touch of color on the table.

Home in Winter Garden

Downtown Winter Garden, Florida

Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.

The living area features a black leather couch adorned with colorful cushions, set on a soft blue area rug. A dining table with white chairs is positioned nearby. Bright light enters through sliding doors, while modern décor, including a painting and potted plants, enhances the space.

4.78 out of 5 average rating, 185 reviews

Renovated home 12-25 min Airport &Universal Disney

Looking for a place to host your group at a private home, for a few days or over a month?! We have a house just for you, located in a charming neighborhood near major attractions in Orlando. ✔Airport is 12-15 minutes away and the theme parks are 20-30 minutes away! This ✔clean, decorated, 4-bedroom, 2-bathroom house with a ✔full kitchen can comfortably host ✔8-10 guests for a relaxing vacation or work retreat. We hope you enjoy your stay!

4.87 out of 5 average rating, 154 reviews

The spacious backyard features an in-ground swimming pool surrounded by a paved deck. Lounge chairs and colorful pool toys enhance the area. A covered seating space and dining area are visible, providing options for relaxation and dining under the sun.

Home in Sky Lake

POOL home with Mini Golf! 3 BR/1BA

Welcome to your spacious POOL home located in a quiet neighborhood in Central Orlando! - 10 minutes from airport - 15 minutes from Universal - 25 minutes from Disney Enjoy this cozy & fun 3 bedroom, 1 bathroom home that sleeps up to 8 people comfortably. The LARGE backyard is a true sanctuary with a stunning pool with plenty of patio space to relax, whine down and enjoy the Florida sun. Please read full description before booking!

4.99 out of 5 average rating, 139 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

This home was designed with the idea of imagination in mind. Imagination can take you to places you otherwise could have only dreamt of being in; Walt Disney himself said, "If you can dream it, you can do it". The vibrancy and life that fills this house represents imagination. When you set foot in this house, the real world fades away. Here, life can be a rainbow. People of all abilities are welcome to sing, dance, and have fun here.

4.97 out of 5 average rating, 205 reviews

A spacious bedroom is centered around a comfortable bed covered with a soft, turquoise blanket. A collection of artwork adorns the wall above the bed, while a lamp and a potted plant provide thoughtful accents. An open doorway leads to a kitchenette area in the background.

Guest suite in Orlando

Modern and luxurious studio

Come and enjoy a stay with all the comforts that a hotel room can offer you, with totally independent access and private parking. Only 5 minutes from the Florida Mall, which is the most important shopping center in Central Florida. The space offers a studio with a kitchen, laundry area, and bathroom. Located just 12 minutes from Orlando International Airport (MCO) and only 19 minutes from Universal studio.

4.98 out of 5 average rating, 273 reviews

A charming outdoor patio area is presented, featuring a table with four black chairs and an umbrella for shade. A low wall defines the space, complemented by potted plants and a grassy area. The tiny home entrance is visible, framed by a wooden porch.

Tiny home in Sky Lake

Private Tiny Home w/ Yard + Grill

🌿 A cozy family retreat! Perfect for 2 guests, but can host up to 4. Parents can enjoy a private bedroom with a queen bed, while the spacious loft with two twin beds offers a fun and comfy sleep space for kids or extra guests. There’s also a full-size sofa bed, plus a full kitchen, washer/dryer, and a private patio to relax. Located in a quiet neighborhood just 15 mins from Universal and 27 from Disney. 🏡✨

4.98 out of 5 average rating, 406 reviews

Guest suite in Sky Lake

~Chic Oasis • 6-Guest Suite • Pool Heat • Near All

From our family to yours, welcome to our Elegant Oasis in Orlando. Enjoy a fully equipped guest suite with access to a heated pool and shared backyard, just minutes from Disney, Universal Studios, and the NEW Epic Universe. Unwind in comfort and style after exploring world-renowned attractions. We are dedicated to making your stay unforgettable and look forward to welcoming you again soon. 😊

Popular amenities for Pine Castle family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The open-plan living area features a spacious dining table surrounded by elegant chairs, complemented by designer lighting. A comfortable sectional sofa is positioned opposite a large TV, while large windows allow natural light to illuminate the room.

4.96 out of 5 average rating, 159 reviews

Vista Cay Luxury Vision, Next to EPIC and OCCC

4.88 out of 5 average rating, 105 reviews

No Airbnb Fees! Themed Home/Pool/SPA/Resort 243621

The spacious living area features comfortable seating arrangements, large windows, and a decorative area rug. The view leads to the private screened-in pool, providing a seamless indoor-outdoor experience. The room is illuminated by natural light and complemented by a modern ceiling fan.

4.99 out of 5 average rating, 146 reviews

Game & Theater Room, Castle Bunks, Pool & Spa

4.96 out of 5 average rating, 145 reviews

A clear glass rests on a table beside a cozy lounge chair, accompanied by a notepad featuring a puzzle. The background showcases a tranquil private pool enclosed by protective screening, with sunlight reflected on the water's surface.

Villa in Kissimmee

⁕ Disney parks! Luxury resort villa • Private pool

4.93 out of 5 average rating, 161 reviews

A private, screened-in pool area features a sparkling blue pool with a built-in hot tub on one side. Sunlight reflects off the water, creating a serene environment, while surrounding greenery provides a sense of privacy.

Home in Clermont

Stylish Villa Private Pool-SPA Near Parks Disney!

4.99 out of 5 average rating, 156 reviews

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.

Home in Davenport

Spectacular! Disney/Universal Themed Home

4.91 out of 5 average rating, 253 reviews

A private pool area is surrounded by a screened enclosure, featuring a jacuzzi spa and lounge chairs. The pool is inviting, with light blue water reflecting the sky's pink and purple hues. A serene lake is visible beyond the pool, adding to the tranquil setting.

Villa in Kissimmee

House by the Mouse: Something for Everyone!

4.96 out of 5 average rating, 104 reviews

IS1-107 - Orlando Condo Near Disney | 2BR

Family- and pet-friendly home rentals

A serene pool area is surrounded by lush landscaping and tall palm trees, with sunlight glistening on the clear water. The pool features a gentle curve, and a white fence encloses the backyard, providing privacy and a sense of tranquility.

4.86 out of 5 average rating, 163 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

A spacious living area features a modern sectional sofa and two blue lounge chairs. A large flat-screen television displays a fireplace design, creating a cozy focal point. Natural light fills the room through window coverings, and a potted plant adds a touch of greenery.

4.92 out of 5 average rating, 242 reviews

Cozy House with Private Pool. Kissimmee/Orlando

A spacious living area is displayed, featuring a sectional sofa and a large wall-mounted TV. The open kitchen showcases modern appliances and a dining table for six. Natural light floods the space through sliding glass doors that lead to the backyard.

4.97 out of 5 average rating, 166 reviews

Beautiful House Completely Remodeled

Home in Buenaventura Lakes

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

4.89 out of 5 average rating, 115 reviews

Villa Resort Club

Home in Colonialtown South

A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.

4.97 out of 5 average rating, 163 reviews

Private pool home near Downtown

4.9 out of 5 average rating, 505 reviews

A bright bedroom is presented, featuring a spacious bed with crisp white linens and a decorative orange pillow. Soft overhead lighting highlights the warm tones of the wooden headboard. The room includes an ensuite bathroom, visible through an open door, enhancing accessibility.

Apartment

Westgate Palace Resort 2 bedroom

4.94 out of 5 average rating, 159 reviews

A cozy living area features comfortable seating and a flat-screen TV, complemented by light streaming in through white blinds. A well-equipped kitchen is visible in the background, and an inviting bedroom with a king bed is seen alongside a detached private sauna, surrounded by lush greenery.

Cottage in Orlando

Mills Lakeside

The open living area features modern decor with a neutral palette and touches of greenery. A comfortable seating arrangement includes a black sofa and an accent chair. Large glass doors allow natural light to fill the space, connecting the indoors to the outdoor pool area.

4.98 out of 5 average rating, 103 reviews

The Perfect Home - Heated Pool - Next to Universal

Family-friendly home rentals with a pool

4.67 out of 5 average rating, 12 reviews

Home in Edgewood

Modern Poolside Bungalow in the Heart of Orlando

4.97 out of 5 average rating, 33 reviews

A shared private pool area features a clear blue pool surrounded by light-colored paving stones. Palm trees and green foliage are visible in the background, with a serene lake reflecting the sky. Lounge chairs are arranged nearby, providing a relaxing outdoor space.

Guest house in Orlando

Lakeside Palm Escape

5 out of 5 average rating, 80 reviews

A screened-in pool area showcases a private swimming pool surrounded by loungers in teal. Colorful pool floats are visible in the water. Lush greenery provides a backdrop, while the sun shines brightly overhead, contributing to a refreshing outdoor space.

Home in Oak Ridge

Harmony | 10 Min Universal Studios | Heated Pool

A spacious bedroom features a large bed with a light-colored duvet and decorative pillows. Nightstands with stylish lamps are positioned on either side of the bed. Natural light enters from a window adorned with sheer blinds, illuminating the warm wood flooring.

5 out of 5 average rating, 12 reviews

Casa Lucia Lakeview condo @vista Cay Close to OCC

5 out of 5 average rating, 14 reviews

3BR Presidential-Bonnet Creek-On Disney Grounds!

5 out of 5 average rating, 3 reviews

Home in Oak Ridge

Amazing Pool-Jacuzzi/ 8 Universal/ 15 Disney

4.86 out of 5 average rating, 145 reviews

A modern kitchen features a large, white island at its center, complemented by stainless steel appliances. Sunlight streams through arched windows, illuminating the light grey walls and spacious layout. Wood-like flooring adds warmth, while a cozy living area is visible in the background.

Home in Ocoee

Come as a guest and leave as family, everyone does

A clear view of a private pool surrounded by lush palm trees and a pavered patio. The pool features a unique shape with smooth edges, and white spheres float gently on the water's surface, reflecting natural light.