
Family-friendly vacation rentals in Hollywood
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Top-rated family-friendly rentals in Hollywood
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★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*
4.98 out of 5 average rating, 777 reviews
Daniel Island Studio For Your Enjoyment!
Finished Room over Garage in historic Charleston, SC, is a cozy and beautiful living space with a full bath and kitchen, as well as a washer/dryer. Conveniently located in Smythe Park, just a mile away from downtown Daniel Island with shops and grocery store (Publix). Approximately 20 - 25 minutes from downtown Charleston. Accessibility limitations: this space requires walking 16 steps to access, and there is not a grab bar in the bath. No pets, smoking, or partying please. Permit #00711
4.92 out of 5 average rating, 306 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!
4.93 out of 5 average rating, 213 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!
4.94 out of 5 average rating, 140 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!
4.97 out of 5 average rating, 164 reviews
Beautiful 2BD/2BA Seabrook Island Villa
Enjoy beach living in this beautiful two bedroom, two bath villa! Just 23 miles from downtown Charleston, Seabrook is a gated, 2200 acre resort community with multiple luxury amenities. This end unit villa overlooks the 15th fairway on Crooked Oaks golf course, and is just steps away from a private pool available only to residents and guests of Live Oak Villas. Beach and pool access, Seabrook Island Beach Club, and dining with spectacular views of the ocean, are located only a mile away.
4.95 out of 5 average rating, 186 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
4.98 out of 5 average rating, 254 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
4.97 out of 5 average rating, 153 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!
4.94 out of 5 average rating, 126 reviews
Charleston Charm ~ Sleeps 10!
This home features 4 well appointed bedrooms, including 2 King and 3 Queen beds. Centrally located to big businesses like Boeing and Bosch, just 10 minutes from the Charleston International Airport, 25 minutes to downtown and 30-40 minutes to local beaches. Enjoy sipping coffee on the private back patio, make breakfast in the cozy kitchen and sit around the table for a big family meal. Why stay in a hotel, when you can relax in the comfort of home!
4.94 out of 5 average rating, 109 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.
4.94 out of 5 average rating, 266 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.
4.97 out of 5 average rating, 116 reviewsPopular amenities for Hollywood family-friendly rentals
Family-friendly home rentals with a hot tub

Heated Pool - Marsh Front - Hot Tub - Walk toBeach
4.83 out of 5 average rating, 222 reviews
Pleasant Place New Build + Pool Great for Families
4.89 out of 5 average rating, 178 reviews
Winter hot tub retreat • Walk to Beach/Restaurants
4.96 out of 5 average rating, 191 reviews
The Endless Summer-Hot Tub-7 beds
4.93 out of 5 average rating, 244 reviews
Luxury Beach Front Pet Friendly
4.89 out of 5 average rating, 221 reviews
Waterfront Home 5 minutes From Downtown Charleston
4.82 out of 5 average rating, 408 reviews
Private HotTub•Comfy Beds•Fenced•Central Location
4.9 out of 5 average rating, 251 reviews
Gated Farmhouse Loft with Pool & Hot Tub
4.95 out of 5 average rating, 288 reviewsFamily- and pet-friendly home rentals

Pet friendly 4BR home Near Magnolia and Middleton
4.91 out of 5 average rating, 107 reviews
Hart Estates: 2 bedroom retreat on Wadmalaw Island
4.98 out of 5 average rating, 106 reviews
The James: “Tiny” Home b/w Downtown & Folly
4.98 out of 5 average rating, 269 reviews
Full Fence/King Suite/Open floor plan
4.95 out of 5 average rating, 123 reviews
Charleston Charmed Cottage - 3 bd/2ba
4.97 out of 5 average rating, 258 reviews
4BR Family Home | Kids + Pets | Folly Beach 12mi
4.9 out of 5 average rating, 160 reviews
Comfy Condo Close to Everything
4.94 out of 5 average rating, 125 reviews
St. Helena Waterfront Retreat
4.97 out of 5 average rating, 119 reviewsFamily-friendly home rentals with a pool

Crushing on Charleston *Pool *Game Room *Fire Pit
4.99 out of 5 average rating, 134 reviews
Little Oak Love | 5 Minutes to Folly | Marsh View
4.97 out of 5 average rating, 271 reviews
Kiawah Island Home w/ Pool - 4 bedroom /4 bath
4.83 out of 5 average rating, 173 reviews
Marshfront 5BD Oasis | Pool, Yard & Steps to Beach
4.97 out of 5 average rating, 190 reviews
Turtle Beach | Live Oak House, Kiawah Island
4.98 out of 5 average rating, 119 reviews
Gorgeous home one block from beach w/ heated pool
4.97 out of 5 average rating, 118 reviews
Sunset Villa- Across From Beach & Close to Pool!
4.91 out of 5 average rating, 122 reviews
Charming Charleston townhouse!
4.9 out of 5 average rating, 266 reviewsDestinations to explore
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- Sullivan's Island Beach
- Isle of Palms Beach
- Hunting Island State Park Beach
- Charleston City Market
- Bulls Island
- James Island County Park
- College of Charleston
- North Charleston Coliseum & Performing Arts Center
- Waterfront Park
- Rainbow Row
- Riverfront Park
- Shem Creek Park
- Magnolia Plantation & Gardens
- Hampton Park
- Edisto Beach State Park
- The Charleston Museum
- Middleton Place
- Hunting Island State Park
- Shelter Cove Towne Centre
- White Point Garden
- Angel Oak Tree
- Kiawah Beachwalker Park
- Cypress Gardens
- Boone Hall Plantation





