Family-friendly vacation rentals in Hollywood

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Hollywood

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

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Top guest favorite

An airy loft space features a suspended wooden swing, inviting relaxation under the high, timbered ceilings. Natural light streams through large windows, illuminating cozy furnishings including a bed and a dining area with a wooden table. Unique decor elements enhance the overall character.

Guesthouse in Summerville

4.98 out of 5 average rating, 775 reviews

★Delightful guest house near historic plantations★

Nestled in the Historic Plantation District between Summerville & Charleston, our timberframe "bunkhouse" offers privacy, comfort & convenience. This 850+ sq ft retreat includes full kitchen & bath, 2 dbl beds, twin bed & plenty of living space. There's a private entrance, so come & go as you please (we're right next door if you need us). Minutes from Middleton Place, Drayton Hall & Magnolia Gardens, an easy drive to dntn Charleston, historic S'ville, beaches & golf courses. *Now with WiFi*

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Top guest favorite

A vibrant sunset paints the sky in hues of orange and purple, reflecting beautifully on the calm waters of the Stono River. Silhouetted trees frame the horizon, while the serene landscape offers a peaceful atmosphere.

Cottage in Johns Island

4.93 out of 5 average rating, 213 reviews

Stono River Retreat - Waterfront.

New cozy wood cabin tastefully decorated, situated among the live oak trees on the Stono River (ICW). Cabin is convenient to downtown Charleston, the white sand beaches of Kiawah Island and Folly Beach. Enjoy nearby sights and fabulous local food. End your day relaxing on the screened porch and deck overlooking the serene Stono River & the sunsets! Enjoy the water by launching your kayak or boat on the Stono River at the Limehouse boat landing, just 2 miles away. Abundant wildlife viewing!

Indoor spacesKitchenLong stay

Guest favorite

A serene pathway leads from the grassy area towards a wooden dock extending into the calm waters of the Stono River. Lush greenery is visible on either side, framed by a tall palm tree and dotted with low shrubs, under a clear blue sky.

Home in Johns Island

4.94 out of 5 average rating, 139 reviews

Waterfront home w/ Deepwater dock on Stono River!

3bd/2bath waterfront home with deep water dock on the Stono River on Johns Island! Beautiful lot in quiet neighborhood, with large majestic live oaks. Enjoy beautiful views of the Stono River from the sunroom or patio, ideal for catching pretty sunsets! Great fishing and crabbing right off dock as well as boating, kayaking, or swimming. Bring your own boat to keep at dock! Located across from public boat landing! 2 kayaks, crab pot and 4 bikes included. Come and enjoy this beautiful property!

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Top guest favorite

Guesthouse in Hollywood

4.97 out of 5 average rating, 163 reviews

Farm Stay w Gardens, Cute Animals, Firepit + Porch

Welcome to the farm! This cute little farm studio is ready for your enjoyment! With a horse-front view and rows of flowers in sight, you will be sure to soak in all the feels of farm life, all while being close to West Ashley, 30 minutes from Downtown Charleston, and 35 min from beach access. Tucked in behind the hustle and bustle of city life, you can put your feet up and relax, walk the gardens, or check out the cute farm animals. Truly, this is a unique stay that you don't want to miss!

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Guest favorite

A charming blue house with white shutters is presented in a landscaped yard. Solar panels top the roof, and a bold red front door welcomes visitors. The driveway leads to a single-car garage, framing the home's inviting exterior.

Home in West Ashley

4.91 out of 5 average rating, 107 reviews

Pet friendly 4BR home Near Magnolia and Middleton

Kick back and relax in this calm, stylish home just minutes from some of Charleston's most popular attractions. This home is a perfect central location as you explore all Charleston has to offer. The home is situated on a quiet street with plenty of privacy and convenience. 3-6 mi to 3 of the historic plantations and gardens 8 mi to the N Charleston Coliseum 9 mi to downtown 9 mi to the airport 11 mi to historic Angel Oak tree 12 mi to Park Circle in North Charleston 17 mi to the beach

KitchenFamilyWalkability

Guest favorite

The exterior of a single-story house is displayed, featuring a light grey facade and a welcoming entrance. A gravel driveway leads to the parking area. Surrounded by lush greenery, the yard offers ample space for outdoor activities.

Home in Johns Island

4.96 out of 5 average rating, 121 reviews

Full Fence/King Suite/Open floor plan

Bring the whole family to this great place with lots of room for fun. Yard is fully fenced. Located in the heart of Johns Island, nearby many restaurants, breweries and the famous angel oak tree. Guests love the location since it is away from the hustle and bustle of downtown, but still with 30 minutes of Kiawah, Folly Beach, and downtown Charleston One of few licensed operators on Johns Island. Book with us and rest assured we won’t get shut down before your arrival. ZSTR-12-24-01051

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Guest favorite

The exterior of a brick ranch house is visible, showcasing a well-maintained front yard with greenery and a large tree. A driveway leads up to a single-car garage with a white door. The entrance features a covered porch highlighted by light blue shutters.

Home in James Island

4.89 out of 5 average rating, 216 reviews

Make Yourself at Home

Brick ranch, conveniently located between Downtown Charleston and Folly Beach, 5 minutes to King Street, 20 minutes to Mt. Pleasant and 30 minutes to airport. Full house with 3 bedrooms, 2 bathrooms, open kitchen, dining room and large living room with big screen tv. A screened porch, fenced in backyard, washer & dryer , on site parking for 4 vehicles. Walking distance to 2 playgrounds, tennis court, wildlife sanctuary, state park and a great view of Fort Sumpter and the city.

FamilyIndoor spacesLong stay

Top guest favorite

A spacious bedroom features a black metal bed frame adorned with white bedding. Two stylish chairs are positioned beside large windows offering views of the surrounding landscape. A wooden dresser and a woven area rug add elements of comfort and warmth to the room.

Guesthouse in West Ashley

4.98 out of 5 average rating, 252 reviews

Large Guesthouse with Private Dock & Marsh Views

This newly built carriage house is separate from the main house. The cottage is about 1,200 sqft so it very open and spacious and great views of marsh and our tidal creek. We have a separate work area with desk and a massive dinning table if you need more room to work or to gather with friends. Full kitchen, washer and dryer, massive shower, the list goes on. You may not want to leave! Feel free to go sit and have coffee or cocktails on the dock. PERMIT# OP2025-06925

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Guest favorite

A comfortable living area features a light-colored couch and a cozy armchair, paired with a side table. A large television is mounted above a fireplace, while windows allow natural light to brighten the space. Decor includes wall art and a decorative clock.

Home in North Charleston

4.97 out of 5 average rating, 151 reviews

Charming 3 bedroom home in North Charleston

This home is perfect for a getaway with the family, or time away with friends! Cozy up on the comfy couch as you entertain yourself with a good book or watch something on the 65in smart tv. Entertaining your family and friends is easy with arcade room classics like Ms. Pacman, Marvel vs. Capcom, and Mortal Kombat amongst many others. 20 minutes from downtown and 30 minutes from the beautiful beaches! City of North Charleston Short-Term Rental Permit 2026-0488

FamilyIndoor spacesSleep quality

Guest favorite

A serene waterway is flanked by lush greenery and reflected clouds, creating a peaceful natural landscape. The calm waters mirror the sky, with a boat visible in the distance, indicating opportunities for exploration and relaxation.

Home in Johns Island

4.94 out of 5 average rating, 126 reviews

The River Girl, Private Dock, Great Outdoor Spaces

The River Girl is located on Johns Island, a beautiful 20 min drive to downtown Charleston, 20 min to Kiawah, & 20 to Folly Beach. We hope this place provides a comfy spot to rest your head at the end of a fun day exploring. We also want you to take advantage of the slow island life! Go crabbing off the dock and cook your supper! Read a book on the back deck & enjoy the breeze. Light a candle, & take a soak in the tub! Just enjoy yourself. Fully updated!

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Top guest favorite

A spacious pool area is surrounded by lush greenery, featuring vibrant tropical plants. Poolside seating includes lounge chairs, shaded by colorful umbrellas. A patio area is visible, designed for outdoor gatherings, with a backdrop of natural beauty enhancing the serene atmosphere.

Apartment in Johns Island

4.94 out of 5 average rating, 265 reviews

Sailors Rest: Pool & Sauna Johns Island SC Retreat

Escape to Sailors Rest, a Johns Island oasis located just a short drive from Charleston, SC & Kiawah Beach. We offer a unique blend of lush gardens, tropical vibes, & natural beauty, complete with pool, infrared sauna, farm-fresh eggs, 2 Queen beds, fireplace & patio. You would be the only guests on the property. Hosts live on premises. Book Sailors Rest now if you’re looking for friendly southern hospitality and Caribbean inspired living.

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Top guest favorite

A serene cottage sits beside a calm pond, reflecting the surrounding trees. The structure features a spacious porch with rocking chairs, framed by palm trees. Large windows and skylights invite natural light, enhancing the connection with the tranquil outdoor environment.

Cottage in Johns Island

4.97 out of 5 average rating, 116 reviews

Quiet Cottage | Waterfront | Fire Pit

Welcome to our scenic waterfront retreat on Johns Island.We are a handicap friendly cottage with large, flat doorways and no steps. This 2-bedroom, 2-bathroom single-level home offers woods and garden views.There is a dock to Church Creek where you can fish, crab and kayak. The roads are great for walking and biking.. Families and couples will enjoy the serene beauty and wildlife at this comfortable, hidden gem.

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