Vacation rentals in Hollywood

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Top-rated vacation rentals in Hollywood

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

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Guest favorite
A cozy living space is illuminated by natural light streaming through a large window, framed by greenery. A comfortable sofa, adorned with decorative pillows and a warm throw, invites relaxation. A glass coffee table rests atop a patterned rug, complementing the subtle decor.
Guesthouse in James Island
4.95 out of 5 average rating, 127 reviews

Casa de Fig

Casa de Fig is a travel and beach inspired guesthouse providing you with all you need to dive into Charleston - newly built and quietly tucked away next to neighborhood parks and multiple water access points. We’re located in Riverland Terrace, one of Charleston's most quintessential neighborhoods on the water. Known for its central location to Folly Beach and downtown and it's walkability to neighborhood restaurants, bars, the Terrace movie theater, the PourHouse music venue, & farmers market.

Top guest favorite
Guesthouse in James Island
4.99 out of 5 average rating, 110 reviews

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!

Top guest favorite
The spacious interior of the loft is characterized by a high ceiling with exposed wooden beams. A large, swinging sofa offers comfortable seating, while a rustic coffee table and a well-equipped kitchen with wooden cabinetry are visible in the background. Natural light filters through large windows.
Guesthouse in Summerville
4.98 out of 5 average rating, 760 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
Home in Johns Island
4.94 out of 5 average rating, 131 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!

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, 213 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
Guesthouse in James Island
4.98 out of 5 average rating, 248 reviews

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

Top guest favorite
Guesthouse in Hollywood
4.97 out of 5 average rating, 141 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 favorite
A circular fire pit is surrounded by six black Adirondack chairs, situated on a gravel patio. The spacious private backyard features lush green grass and a cozy setting, with a brick grill positioned nearby and the renovated home visible in the background.
Home in West Ashley
4.98 out of 5 average rating, 114 reviews

Southern Dream - Spacious Home w/ Fire Pit & Patio

Welcome to our beautifully renovated home! Perfect for creating unforgettable memories together. Picture cozy nights around the fire pit in the spacious private backyard, fun barbecues with the outdoor grill, and laughter-filled evenings on the charming covered patio. You'll also enjoy: Free laundry Smart TV's in all rooms Fully stocked and equipped kitchen Extremely safe neighborhood Free parking You are only: 10 mins to Avondale 15 mins to Downtown Charleston 30 mins to Folly Beach

Guest favorite
Guest suite in West Ashley
4.9 out of 5 average rating, 572 reviews

Spend the Night in a Photographer's Studio!

This bright and clean mid century modern style bedroom is a great retreat for couples, solo, and business travelers. Some features include dual shower heads, private washer & dryer and cozy seating area. Only 12 minutes to the airport and 4 minutes to I-526, the location is considered “centrally located.” 7 miles from downtown Charleston. 14 miles to Folly Beach. Close to many of the most popular wedding venues, plantations, and all the secret places the LowCountry has to offer.

Top guest favorite
The exterior of the carriage house is illuminated at night, showcasing its architectural features against the tranquil waters. Surrounding greenery and reflections of the buildings in the water create a serene atmosphere, complemented by the soft glow of outdoor lights.
Guesthouse in West Ashley
4.98 out of 5 average rating, 245 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 favorite
Home in Hollywood
5 out of 5 average rating, 39 reviews

Waterfront Retreat, 3 Suites, Pets OK

Welcome to your own peaceful waterfront retreat nestled in nature. This 3-bedroom, 3-bathroom home offers luxury and comfort with natural water views. Enjoy serene mornings on the porch, bike scenic trails, hike nearby parks, or fish from the bank. Just 30 minutes from Edisto Beach and 40 minutes from Downtown Charleston, this secluded getaway offers the perfect blend of tranquility and adventure. Whether unwinding or exploring, Respite Cove is your ideal sanctuary.

Top guest favorite
Cottage in Johns Island
4.97 out of 5 average rating, 429 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!

Popular amenities for Hollywood vacation rentals

When is the best time to visit Hollywood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$16,735 GYDG$16,735 GYDG$16,945 GYDG$22,593 GYDG$24,476 GYDG$24,685 GYDG$23,011 GYDG$17,781 GYDG$18,827 GYDG$18,827 GYDG$21,129 GYDG$18,827 GYD
Avg. temp10°C12°C15°C19°C23°C26°C28°C27°C25°C20°C15°C11°C

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 hotel rentals in Hollywood?

    Experience the best of Hollywood with our hotel rentals, starting at about $80 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 10 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 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.

Quick stats about vacation rentals in Hollywood

  • Total vacation rentals

    Explore 40 vacation rentals in Hollywood

  • Nightly prices starting at

    Hollywood vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,610 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Hollywood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Hollywood rentals

  • 4.6 Average rating

    Hollywood stays receive an average rating of 4.6 out of 5 from guests