Family-friendly vacation rentals in Pine Castle

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pine Castle

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

Home in Kissimmee

4.87 out of 5 average rating, 244 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

Top guest favorite

A quaint exterior view of a small house surrounded by lush greenery. The porch is framed by a railing and features a couple of chairs, while string lights add a charming touch. Colorful flowers bloom in the foreground, enhancing the serene atmosphere.

Guesthouse in Orlando

4.94 out of 5 average rating, 419 reviews

Garden House near Orlando's cultural hub

On a quiet cobblestone street, yet close to art and culture, more than 3 dozen restaurants in walking distance, Florida Hospital and family-friendly activities. You’ll love our place because of the location, the large bathroom with jacuzzi, the skylights, window seat, porch swing. It is nestled in our back yard surrounded by trees and has its own private entrance via a rustic walk way of pavers and stones. Couples, families, most anyone will find it charming. STR 1009942 (City registration)

Guest favorite

The light-filled living room features a stylish gray sofa, wooden side tables, and a coffee table. Natural light enters through the large window, illuminated by soft curtains. Decorative plants enhance the inviting ambiance, complemented by warm wooden flooring.

Home in Orlando

4.91 out of 5 average rating, 105 reviews

Charming 2BR Cottage, Downtown Orlando

Bright, cozy 1940’s cottage located in a quiet, safe, family-friendly Downtown Orlando neighborhood. 2 bedroom, 1 bath, onsite parking, full kitchen, washer and dryer, fenced-in back yard and patio area, working desk space in bedroom. Walking distance to the local gems and eateries of Audubon Park and the Mills 50 District! Central location minutes away from Winter Park and Downtown local attractions. 20-30 minutes from Universal, Disney and MCO. Great for a work trip or an Orlando getaway!

Superhost

A spacious room features a large bed with a decorative coverlet and a matching color scheme. A ceiling fan hangs above, providing airflow. A kitchenette area with a coffee maker is visible, along with a mounted TV on the wall. Bright curtains partially illuminate the space.

Guest suite in Orlando

4.76 out of 5 average rating, 499 reviews

Private Studio by EPIC, IOA ,Disney and Fl Mall

Welcome to Orlando! This private room includes it's own entry and it is completely separate from the house. You will have your own bathroom as well as mini kitchen. Basic essentials such as towels,soap and more will be provided for you and you will be near all of Orlando's most famous attractions! Florida Mall - 4 Minute drive Airport - 11 Minute drive Downtown Orlando - 14 Minute drive Millenia Mall - 14 Minute drive Universal Studios - 15 Minute drive Disney Springs - 19 Minute drive

Top guest favorite

A private pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant greenery. The sparkling blue water of the pool reflects the sky, while a paved pathway leads to the entrance. A serene atmosphere is created by the nearby plants and outdoor decor.

Home in Maitland

4.95 out of 5 average rating, 168 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Guest favorite

A comfortable seating area features a dark gray sectional sofa adorned with decorative pillows. A patterned area rug lies underneath, complementing the wooden floor. A dining table with colorful chairs is visible in the background, alongside a TV stand and natural light filtering through sheer curtains.

Guest suite in Orlando

4.95 out of 5 average rating, 177 reviews

Upscale Urban Chic Apartment

This warm “Carriage House Apartment” offers a cozy relaxed studio suite, it's 500 sq ft in a premiere established neighborhood. Built in 1938, updated for modern fine living with charm. Enjoy scenic views, romantic evening strolls through tree lined streets to nearby parks and lakes. Ample on street parking. Walking distance to shopping, bars, fine dining, the Orlando Regional Medical Center and near major attractions. Live a local’s life in the heart of Orlando, Florida.

Top guest favorite

A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.

Treehouse in St. Cloud

4.96 out of 5 average rating, 991 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Superhost

The living room features a dark sofa adorned with red and gray cushions, complemented by a black coffee table. A bucket chair is positioned nearby. Two small framed photographs hang on the light-colored wall, and natural light filters in through the window beside the front door.

Home in Orlando

4.78 out of 5 average rating, 134 reviews

Comfy 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.

Top guest favorite

A modern living area features a large sectional sofa and a glass coffee table. Natural light floods the space through multiple windows, enhancing the warm wooden flooring. A round dining table is set for four, while a decorative artwork piece adorns the wall.

Condo in Orlando

4.86 out of 5 average rating, 147 reviews

Beautiful Downtown Condo 1/1

This fully furnished 1/1 apartment, comes fully equipped with all the necessities you need for your vacation or short stay to Orlando, The City Beautiful. We have fully remodeled our house and would like to share the experience with you. The bedroom come with California king bed. Our kitchen has pots, pans, plates and silverware, as well as a Nespresso coffee machine for your morning wake up! We have our laundry machines in-house and yes, you can use them.

Top guest favorite

A charming guesthouse is nestled among lush tropical vegetation, surrounded by diverse greenery and tall trees. Sunlight filters through the leaves, casting dappled light on the exterior and patio area, creating a serene and inviting atmosphere.

Guesthouse in Windermere

4.94 out of 5 average rating, 270 reviews

Paradise nook near Orlando's theme parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

Top guest favorite

The exterior of a colonial-style home features inviting porches with several seating arrangements. The main entrance has a prominent door framed by windows, while symmetrical bay windows accentuate the facade. Lush greenery surrounds the property, enhancing the welcoming appearance.

Home in Lake Cherokee

4.99 out of 5 average rating, 178 reviews

Not just 2 private bedrooms; the entire upstairs!

Completely private upstairs apartment. We live on the first floor. We offer two bedrooms, private bath, sitting room/desk and kitchenette, all EXCLUSIVELY yours. TV, coffee, breakfast bars and muffins are provided. Lounge on the front porch or enjoy a leisurely stroll around two beautiful lakes. Walk downtown (15-20 minutes) to restaurants and bars or just around the lake for a relaxing outdoor breakfast.

Top guest favorite

A quaint shed is set amidst a lush green yard, featuring a stone pathway leading to a small outdoor seating area. A round, floral-patterned table is accompanied by two matching chairs. Flowering plants and delicate hanging baskets add a touch of nature to the inviting space.

Tiny home in College Park

4.96 out of 5 average rating, 709 reviews

Tiny House Shed in Downtown

Nestled behind my 1920s bungalow in one of Orlando’s best neighborhoods, The Shed is a local experience. Located in the city center, just a 5 min Uber to Amway, Soccer Stadium, and walking distance to the Sun Rail and hospital. Perfect for couples, traveling professionals, and those new to Airbnb. Note: I rent out my main house, so you may see guests in the backyard. No smoking/vaping.