Holiday rentals in Hollywood

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Top-rated holiday rentals in Hollywood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Two coral-colored armchairs are positioned in the cozy studio, complemented by a set of three white nesting tables. Nearby, a jute rug adds warmth to the space, and the kitchenette is visible in the background with modern appliances and cabinets.
Loft in West Ashley
4.93 out of 5 average rating, 461 reviews

Studio Apartment in Charleston’s Plantation Dist.

Cozy studio apartment w/a private entrance overlooking golf course in quiet neighborhood. Studio located in Historic Plantation District minutes from Middleton Place, Magnolia Plantation, & Drayton Hall w/shopping, downtown, & beaches nearby. Equipped w/a cozy queen sized bed, flat screen TV, Xfinity HD cable, high speed internet, Keurig Coffee maker, kitchenette, washer/dryer, & full bathroom! Inquire for Early Check-In/Late Check out available for additional fee. City Operation #00605

Top guest favourite
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.
Guest house 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 favourite
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
4.95 out of 5 average rating, 111 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 favourite
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, 210 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!

Guest favourite
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.
Guest house in Hollywood
4.98 out of 5 average rating, 108 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!

Guest favourite
A two-story house is shown, featuring a sloped metal roof and white exterior walls. Large windows are displayed at the front, surrounded by a well-maintained yard with green grass and various plants. Mature trees provide shade, creating a serene outdoor setting.
Home in Ladson
4.96 out of 5 average rating, 107 reviews

Gorgeous 2 bed Farmhouse 15 mins from downtown

Forget your worries in this spacious and serene space. Our home welcomes you with 2 beds, 2 baths, a gorgeous fenced in yard, a screened in porch, and a beautiful fountain to calm your mind. All of your day to day conveniences are available in our home allowing you to settle in like it’s yours. Located 15 mins to downtown Summerville, 25 mins to downtown Charleston, and 30 mins to multiple beautiful beaches. For more space check out my other listing: https://www.airbnb.com/h/chucktowneapt

Guest favourite
An outdoor lounge area features a spacious sectional sofa in dark upholstery, surrounding a low wooden coffee table. Potted plants add greenery around the space. A shed with blue siding and double glass doors sits in the background, framed by tall trees and a wooden fence.
Guest house in West Ashley
4.95 out of 5 average rating, 261 reviews

Quaint Cottage Studio in Ashley Forest (Avondale).

Take in the peace, calm, and hospitality of Charleston at this small, quaint, stand-alone cottage. The studio is situated on our property and shares an outdoor lounge and dining area. Located in the neighborhood of Ashley Forest, a small corner of Avondale, you are walking distance to breweries, cafes, wine bars, sushi restaurants and more. Downtown is a 10 minute ride share away, and there is also a bus stop five minutes from the property that will take you to the heart of King Street.

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, 178 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 favourite
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, 130 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.

Top guest favourite
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.
Guest house 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 favourite
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.)

Guest favourite
A spacious living area features a comfortable sofa adorned with decorative pillows. A wooden coffee table sits on a soft area rug, complemented by modern seating around a small dining table. Large windows allow natural light to fill the space, enhancing the inviting atmosphere.
Home in Johns Island
4.87 out of 5 average rating, 171 reviews

Beautiful, Tranquil Home Between Chas & Kiawah

This newly renovated Midcentury Modern style home is situated on Johns Island, half way between Charleston and Kiawah/Seabrook Islands. Whether you enjoy golfing, beach days, or exploring the charm and history of Downtown Charleston, you'll be close to it all. We are 30 minutes to Folly Beach, 24 minutes to Kiawah Island, 27 minutes to Seabrook Island, and 22 minutes to Downtown Charleston.

Popular amenities for Hollywood holiday rentals

When is the best time to visit Hollywood?

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Avg. price$126 SGD$147 SGD$161 SGD$140 SGD$152 SGD$153 SGD$199 SGD$214 SGD$155 SGD$157 SGD$155 SGD$143 SGD
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Quick stats about holiday rentals in Hollywood

  • Total holiday rentals

    Explore 40 holiday rentals in Hollywood

  • Nightly prices starting at

    Hollywood holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Hollywood holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hollywood rentals

  • 4.8 Average rating

    Hollywood stays are highly rated by guests – averaging 4.8 out of 5!