Family-friendly vacation rentals in Hollywood

Hart Estates: 2 bedroom retreat on Wadmalaw Island

Cozy Coastal Escape on Beautiful Wadmalaw Island 🌊 Unplug, unwind, & experience true Lowcountry charm at this peaceful island retreat just outside of Charleston. 🏡 Spacious cozy 2-bedroom home thoughtfully built by the Hart family ✨ Professionally cleaned ☀️ Light-filled spaces perfect for slow mornings & relaxed evenings ⏰ Early check-in when possible (available for an additional fee) 🧳 Complimentary early luggage drop-off 📍Lifelong local host happy to share insider tips & recommendations

Family · Kitchen · Quiet

Cozy Apartment in Secluded Wooded Neighborhood

UPDATE:Brand new king bed!Centrally located to all things “Charleston”! Minutes to Magnolia Gardens, Middleton Place, Downtown, Folly Beach, Angel Oak, and a ton of wonderful places to indulge the taste buds! You will find well thought out accommodations in a cozy loft style setting. This is a completely separate space at the back of my home with its own private entrance and plenty of parking. I provide a stocked coffee bar, mini fridge w/ freezer,and many thoughtful touches throughout the space

Indoor spaces · Kitchen · Air conditioning

★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*

Indoor spaces · Kitchen · Hot tub

Villa overlooking Charleston close to Folly Beach

Nestled in a bird sanctuary on an oak filled tidal creek lot with expansive porch views of Charleston harbor, come share a coffee with friends and family and watch a spectacular marsh morning sun rise. Located minutes to the famous "Edge of America" Folly Beach, beach chairs, coolers and towels are provided for an enjoyable beach excursion. Centrally located, you are a short trip to historical Charleston, James Island County Park Splash Zone, and neighboring barrier islands. Off street parking.

Kitchen · Family · Wifi

Walk to restaurants! New, beautiful & clean home

Welcome to Curlew Corner! A new, private upstairs guesthouse in one of Charleston’s most desirable neighborhoods. With a king bed+sofa bed, this is an ideal spot for couples, friends, or small families looking for a getaway in a beautiful city! Location! The guesthouse is within walking distance to many eateries, bars, a music venue, cinema, farmer’s market, yoga studio, playground, boat landing, and beautiful water views. Close to downtown Charleston and Folly Beach, you can’t beat this spot!

Indoor spaces · Family · Amenities

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!

Kitchen · Family · River

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!

Kitchen · Indoor spaces · Location

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!

Family · Kitchen · Hospitality

The James: “Tiny” Home b/w Downtown & Folly

The James is a unique 530 sq ft retro coastal tiny home located in a gorgeous neighborhood on James Island ◡̈ 10 mins to downtown Charleston 12 minutes to Folly Beach Walking distance to restaurants The James sleeps up to 6 people and 2 dogs (NO PET FEE) & boasts a private fenced yard & patio with an outdoor shower and Clawfoot tub! The James is ideal for solo travelers, couples, families, those traveling w/ their dog(s), those w/ limited mobility and groups of friends. #BNB-2023-02

Indoor spaces · Kitchen · Checkout

Waterfront Nature’s Retreat Cottage 2Bd/2B

Take it easy at this unique & tranquil waterfront getaway where you will be able to enjoy the stunning views of the Ashley river and beautiful sunsets over Magnolia Gardens. The 2 BR Cottage is located on 1.5 acres on private property Whether you are here for work or play, this property is centrally located: Min from airport, outlets, breweries, restaurants, I-26, 526, Boeing, 20 min from DT Charleston 30 min from the beach. NO PARTIES NO SMOCKING NO PET NO SWIMMING NO DOCK ACCESS 5 PERS

Family · Kitchen · Hiking

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

Kitchen · Family · Checkout

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!

Family · Indoor spaces · Outdoor spaces