Holiday rentals in Hollywood

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Top-rated holiday rentals in Hollywood

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Guest favourite
A cozy living room is highlighted by a sectional couch adorned with orange accent pillows. Natural light filters through large windows, illuminating the space. A wooden coffee table rests on a textured rug, while framed artwork adds character to the wall. A doorway leads to an adjoining room.
Guest suite in Charleston
4.98 out of 5 average rating, 177 reviews

The Indigo Cottage

Escape to this meticulously curated lifestyle cottage. The private residence features rustic wood finishes, floor-to-ceiling tile in the bathroom, contrasting furnishings and decor, & an open layout living area and kitchen. Relax in this serene, sunlit space. The space features an amazing master bedroom with a luxury King Size Bed and walk-in closet. Relax on our brand new mattress and fall asleep under the down comforter. The living room boasts a cozy couch with chaise that pulls out into a queen size sleeper (for two). Modern kitchen, with quartz countertops, rustic kitchen island (which can be used as a working desk) and professional stainless steel Frigidaire appliances. Includes; dishwasher, garbage disposal, microwave, stove, refrigerator, coffee pot, toaster/convection oven, electric kettle and all the cookware necessary to create a gourmet meal. Large bathroom with floor to ceiling tile, walk-in shower and large vanity with double sink. You will have two parking spaces. Since it’s a guest cottage located on the back of the property you will be required to walk 50 yards to the building. Follow the gravel walking path, through the gate, along the fence line to reach The Indigo Cottage. We will provide a wagon to tote your belongings to and from the car. The Cottage is located on the second level, therefore you will need to ascend a flight of stairs. Our young family and two dogs live on the property in the main house. Our pups are extremely friendly and love a good scratch. The yard is fully fenced and we frequently let our dogs spend time lounging in the sun. We are happy to be as accommodating as possible during your stay so please communicate with us if your uncomfortable with dogs and we will plan accordingly. The home is nestled in Charleston’s neighborhood of West Ashley, which is convenient to all and safe. 6.9 miles from downtown Charleston (the heart of the historic district and shopping on King Street) 3.5 miles to Whole Foods & Starbucks 2.0 miles from the entrance to 526 state highway 14.3 miles to Folly Beach 15.4 miles to Sullivan’s Island and beach 27 miles to Kiawah Island and beach 9.5 miles to Airport Uber and Lyft are readily available-prices vary with time of day and surcharge pricing. We ask that dogs be housebroken, well behaved, don’t scratch at doors, and don’t bark incessantly while you’re away. There is a lower studio apartment & a non-stop barking dog isn’t appreciated. Please, no pets on the furniture including the couch and bed. Pets MUST be up to date with flea & tick preventive medicine . A maximum of two dogs allowed, an additional cleaning fee of $25 per pet, per stay, is applicable. This is a non-smoking property, we do not allow smoking in the cottage or outside. Thank you for your understanding and cooperation. We will do our best to accomodate early check-in or late check-out. Most days there’s someone checking in the same day there’s a checkout but we try & go above and beyond if this is requested.

Top guest favourite
A spacious sleeping area features a king bed with a simple wooden frame and high-quality linens. Two white dogs sit on the floor, with a neon sign hanging above the bed, stating 'the Folly Beach swell and a Charleston lake.' The room is adorned with tropical-themed decor.
Guest house in Charleston
4.99 out of 5 average rating, 223 reviews

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

The James is a unique NEW 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

Top guest favourite
The exterior view features a light blue house with a porch and a dark green picket fence. A driveway leads to a garage marked with a white door. Lush green grass surrounds the area, contributing to a peaceful atmosphere.
Flat in Daniel Island
4.92 out of 5 average rating, 277 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

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, 748 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 Johns Island
4.95 out of 5 average rating, 117 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, 212 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 favourite
A welcoming living room features a spacious gray sectional sofa paired with patterned accent chairs. A large coffee table sits at the center, surrounded by a textured area rug. Natural light filters through the window with blinds, and a flat-screen TV is mounted on the wall.
Home in Charlestowne Estates
4.99 out of 5 average rating, 136 reviews

Charming 2BR | Near Downtown, Airport & Beaches

Welcome to The Hidden Getaway! Our newly renovated home is located in West Ashley, convenient to local dining & shopping. About 6 miles to historic downtown Charleston, 8 miles to Charleston Int'l Airport, 1.5 miles to Founders Hall & Legare Waring Home at Charles Towne Landing. Craving a beach day? Folly Beach, Sullivan's Island & Isle of Palms are all just a 20-25 minute scenic drive away. Whether here to explore our rich history or savor our incredible cuisine, you'll love our location.

Top 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
4.97 out of 5 average rating, 129 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!

Top guest favourite
The image captures a tranquil pool area illuminated by soft green lights against a backdrop of palm trees. The serene water reflects the surrounding greenery, with a light-colored patio surface complementing the ambiance. The two-story house is partially visible, adding to the inviting atmosphere.
Guest house in Charleston
4.98 out of 5 average rating, 268 reviews

Detached Guest Suite with Pool

Operations Permit # OP2025-5734. Separate entrance to suite. Swimming pool is on veranda . Detached guest suite (45" Smart TV with YouTubeTV ) with full bathroom. Outdoor veranda space includes a swimming pool , outdoor kitchen (microwave,fridge , gas cook top,Keurig (with coffee),toaster, gas fireplace, and large screen Smart TV. The pool is shared with the owners but guests are given privacy. 14 miles to airport 10 miles to downtown Beaches-Kiawah-23 miles. Folly Beach-19 miles.

Top guest favourite
The exterior of the guest house features a mix of textured siding and an intricately designed balcony supported by stylish columns. Surrounded by greenery, it includes a circular window and a swing on the porch, inviting relaxation in a tranquil setting.
Guest suite in Charleston
4.99 out of 5 average rating, 432 reviews

The Garden Folly Guest House

Our architect said, “this is NOT a garage, it’s a Garden Folly!” Our Guest House has a bird’s eye view of the rose covered pecan tree and a vista of the marsh and the Wappoo Creek. When we rebuilt our 1930's garage we saved all the beaded siding and pine floor. My husband enjoyed incorporating many design elements and creative ideas. It was quickly becoming the Taj Garage. We decided it was just the kind of property we enjoy when we travel, so, Voila! we decided to share it with you!

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 Charleston
4.98 out of 5 average rating, 231 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

Top guest favourite
Treehouse in Johns Island
5 out of 5 average rating, 152 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.)

Popular amenities for Hollywood holiday rentals

When is the best time to visit Hollywood?

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Avg. price$125 SGD$145 SGD$159 SGD$139 SGD$150 SGD$152 SGD$141 SGD$109 SGD$116 SGD$116 SGD$130 SGD$116 SGD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Hollywood?

    Hollywood has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Hollywood with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Hollywood?

    Four-legged friends are welcome in Hollywood. Choose from more than 20 vacation rentals for guests traveling with pets.

  • 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.

  • Do hotel rentals in Hollywood have air conditioning?

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

  • 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.

  • 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 hotel rentals in Hollywood have free parking?

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

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 $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,610 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 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!