Vacation rentals in Hollywood

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Top-rated vacation rentals in Hollywood

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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, 724 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*

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 West Ashley
4.94 out of 5 average rating, 109 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 2 bikes included. Come and enjoy this beautiful property!

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, 209 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!

Top guest favorite
A quaint studio space features a warm wood countertop with a sink, complemented by neatly arranged kitchenware. An antique armoire adds character against a textured brick wall. Soft light filters through sheer drapes, illuminating the cozy sleeping area in the background.
Guesthouse in Hollywood
4.98 out of 5 average rating, 106 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 Down Town Charlestion 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!

Superhost
A tiny home exterior is displayed, featuring a mix of dark and warm wood finishes. A spacious deck is furnished with two adirondack chairs and a small table, surrounded by trees and a privacy fence. Surfboards lean against the wall, adding a relaxed touch.
Tiny home in West Ashley
4.85 out of 5 average rating, 175 reviews

Charleston Tiny Home w/ Private Deck +Boat Parking

Welcome to our charming tiny home on the outskirts of Charleston! Nestled in a peaceful neighborhood, this cozy retreat offers a unique and unforgettable experience for your stay. As you step inside, you'll be greeted by a beautifully designed space that maximizes every inch of its compact layout. Outside, you'll find a delightful deck area where you can relax and unwind after a day of exploring. Our tiny home provides easy access to all the attractions that make Charleston so beloved.

Top guest favorite
The exterior of the villa is shown, featuring a light-colored stucco façade contrasted by large windows. Surrounding landscaped areas include planters with vibrant greenery and flowers. A gravel pathway leads to the entrance, framed by the natural beauty of trees in the background.
Home in Summerville
4.93 out of 5 average rating, 128 reviews

Guest House/Villa

Enjoy your stay at this immaculately designed new build Villa. Located on a family property surrounded by 2 acres of trees, in a quiet rural neighborhood. Lots of privacy, peace and quiet, yet only 5 minutes from restaurants and stores. 15 minutes from Downtown Summerville, 40 minutes from Charleston and various coastal attractions. The villa is separate from main house and has no shared space other than the driveway. NO smoking, No pets. Laundry service available for long stays.

Guest favorite
An outdoor patio area features a square stone layout with a firepit at the center. Two wooden chairs are positioned around the firepit, and string lights provide soft illumination in the trees above. A grill is visible nearby, surrounded by greenery.
Guesthouse in West Ashley
4.9 out of 5 average rating, 644 reviews

Cozy Cottage w Games, Firepit, Grill, and More!

Centrally located cottage perfect for exploring the wonders of Charleston! - Amazing location; quick drive to downtown, minutes from Avondale, 12 miles to Folly Beach. - On a beautiful 9 mile bike & walking path - Backyard oasis with games, firepit, grill, and outdoor dining space - Beach chairs, cooler, and umbrella available - Updated interiors with king bed, games, streaming, and fast wifi Enjoy the perfect home base to explore the Lowcountry. We can't wait to host you!

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
4.99 out of 5 average rating, 213 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# OP2024-04998

Top guest favorite
A field of blooming yellow flowers is displayed in the foreground, with delicate petals and green stems. In the background, a white farmhouse is visible, providing a serene country setting. The scene captures the tranquility of the flower field adjacent to the cottage.
Tiny home in Moncks Corner
4.98 out of 5 average rating, 135 reviews

The Goose Cottage at Wild Goose Flower Farm

Located next to the family farmhouse at Wild Goose Flower Farm, The Goose Cottage was designed to immerse guests in our calm and peaceful country life. We are located 15 minutes from the hearts of Cane Bay, Nexton and Exit 194 on I-26, and 45 minutes from Downtown Charleston. Two can sleep in the queen size bed but the sofa also extends into a queen-sized sleeper. Please reach out with further questions or if you would like to inquire about an extended stay.

Guest favorite
An inviting guesthouse is surrounded by lush greenery and vibrant pink flowers, showcasing a wraparound porch with white railings. Tall trees and palm plants create a serene and natural setting, while soft sunlight illuminates the charming structure.
Cottage in Johns Island
4.97 out of 5 average rating, 420 reviews

Captain's Quarters

Nestled at the end of an avenue of Live Oaks, our lowcountry guesthouse offers a peaceful retreat with all of the modern conveniences. Our property is home to beautiful birds, turkey & deer. We are centrally located with easy access to downtown Charleston, Folly, or the airport in 20 minutes, 20 minutes to Kiawah, Seabrook and Wadmalaw Islands. Dinner nearby at Johns Island restaurants, Wild Olive/Royal Tern, or cook up your own fresh catch of the day!

Top guest favorite
The open living area features large windows that frame views of the surrounding trees and creek. Comfortable seating arrangements are present, with two armchairs positioned across from a sofa. Natural light fills the space, highlighting the wood flooring and inviting atmosphere.
Treehouse in Johns Island
5 out of 5 average rating, 132 reviews

Waterfront Treehouse

Marsh and creekside Luxury Treehouse nestled among historic Grand Oaks. Private Elevated TreeHouse that has closeup views of trees and wildlife from every oversized window. Sit back and relax on the large deck watching the ebb and flow of the tide as fish jump, birds hunt and fiddler crabs defend their bank. (This property has been granted an exemption and does not accept pets or Service animals due to allergies.)

Top guest favorite
A charming two-story house is set among lush landscaping, with a spacious lawn and shaded by large trees. A gravel driveway curves toward the home, while a detached garage is visible on the left, providing convenient parking options.
Guesthouse in Johns Island
4.98 out of 5 average rating, 281 reviews

Private waterfront apt in the oaks

Romantic get away for nature lovers. Private 2nd floor studio apartment over garage (guest parking), nestled among large live oaks overlooking tidal creek & dock on wooded property. Less than 30 minutes from downtown Charleston, Folly Beach, Kiawah. Shrimp, fish, crab or just enjoy the hammock on the dock. Or go for a paddle in one of the kayaks provided for a small fee.

Popular amenities for Hollywood vacation rentals

Quick stats about vacation rentals in Hollywood

  • Total rentals

    40 properties

  • Nightly prices starting at

    $50 before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Hollywood?

    Yes! Work meets play with ease at over 20 vacation rentals in Hollywood featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Hollywood?

    Hollywood has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Hollywood have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Hollywood. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Hollywood?

    Experience the best of Hollywood with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Hollywood have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Hollywood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Hollywood have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Hollywood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Hollywood have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Hollywood. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Hollywood?

    Four-legged friends are welcome in Hollywood. Choose from more than 10 vacation rentals for guests traveling with pets.

Destinations to explore