Holiday houses in Callawassie Island

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Top-rated holiday rentals in Callawassie Island

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

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Top Guest favourite

A charming A-frame structure is elevated on a wooden deck, surrounded by lush foliage. The entrance features a white door framed by large windows, allowing natural light to illuminate the space. A small staircase leads to the inviting porch with bright yellow chairs.

Treehouse in Saint Helena Island

4.99 out of 5 average rating, 175 reviews

"A" Secluded Quiet Oasis w/ Beach Pass

Detox You'll love this unique and romantic escape. Architectual design allows you to fully take in the view of the lowcountry marsh. The backdrop of the bed allows you to fall asleep to the majestic starry filled night sky! Soak your cares away with a bath that will surely relax and unwind you. The background is breathtaking! The outside shower allows you to take in the scenery while enjoying a hot shower. This is an "unplug" listing, no tv or internet access. Hunting Island Beach Pass included.

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Top Guest favourite

A spacious studio apartment is shown, featuring a king size bed draped in a patterned quilt. A dresser and lamp are positioned nearby, while a modern kitchen area is visible in the background. Natural light fills the room, highlighting the warm wooden flooring.

Apartment in Bluffton

4.99 out of 5 average rating, 230 reviews

Sunset on the May / Historic Old Town Bluffton

Spacious studio apartment sits above a detached garage with your own private entrance located in the heart of Old Town Bluffton. A short stroll to nearby restaurants, boutiques and unbelievable sunsets on May River. New king size bed, appliances and large sectional couch. Full kitchen with plenty of space to relax and store your things. Nice size bathroom, full shower and an abundance of amenities like private fire pit, outdoor grill and patio table for your enjoyment. HH Beaches minutes away!

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Top Guest favourite

Townhouse in Okatie

4.93 out of 5 average rating, 30 reviews

Lux|Free Golf|Heated Pools|Free Bikes|Parris Is

Perfect for golf escapes, military families, or nearby family gatherings! • 2 Complimentary Rounds of Championship golf per day ($250 day value) • Free bike rentals • 3BR/2BA on beautiful Callawassie Island • Sleeps 6 with king, queen, and twins • 2 heated/cooled pools, tennis, and pickleball • 2 on-site restaurants • <30 mins to Beaufort • 30 mins to Bluffton & Parris Island • <60 mins to Hilton Head & Savannah • <90 mins to Charleston Discover charm, luxury, and adventure all in one place!

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Top Guest favourite

Apartment in Bluffton

4.99 out of 5 average rating, 473 reviews

Guest House on Lawrence Street

UPDATED LUXURY, FASTIDIOUS CLEANLINESS in historic OldTown Bluffton’s coziest carriage house. OldTown’s vibe is just plain fun. Stoll 2 blocks to super restaurants, night life, art galleries, boutiques, antebellum homes & lush waterfront parks on the idyllic May River. New in 2018 w/ quartz counters, private bedroom w/ plush king-size bed, upscale bath w/ soaking tub, bright living/dining room, full kitchen & romantic rocking-chair porch up in moss-draped oaks. Read our Reviews—guests love it!

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Top Guest favourite

A wooden staircase descends towards a dock on serene waters, framed by tall grasses. A blue roofed structure is positioned at the water's edge, with boats visible nearby. The sky is partly cloudy, reflecting natural light onto the calm surface.

Home in Beaufort

4.95 out of 5 average rating, 110 reviews

Belle Monte (beautiful mountain) on the water!

Belle Monte is a lovely light-filled 2 story home on high bluff overlooking Middle Creek off the Whale Branch river in Beaufort, SC. See gorgeous sunrises & watch the dolphins from the upstairs deck or sun porch. Great views of the water from most of the house. New lighted dock on deep water so bring your boat! Enjoy swimming (ladder provided), kayaking or paddle boarding. Great area for fishing and crabbing. Well-equipped kitchen, fireplace, gas grill, screened-in porch, game table & more!

ValueFamilyOutdoor spaces

Top Guest favourite

A private screened-in dock features a swing bed adorned with decorative pillows, offering a cozy resting space. Ambient Edison lights create a warm glow, while views of the marshland are visible through wooden frames and open spaces.

Cottage in Tybee Island

4.99 out of 5 average rating, 205 reviews

Private Dock | FREE Golf Cart, Kayaks & Bikes

Welcome to Siren & Seafarer Cottage! Immerse yourself in all that Tybee Island offers with your own FREE GOLF CART, BIKES, & KAYAKS. Pamper yourself with this luxurious getaway and nature-lover's paradise. Relax on your PRIVATE DOCK on a cozy swing bed while surrounded by panoramic views of the tidal creek. Nestled amongst enchanting live oaks and marsh-side scenery, you'll soon discover something inherently romantic about this Tybee Island cottage, just 25 minutes to downtown Savannah.

LocationValueQuiet

Top Guest favourite

A well-lit living area features a comfortable sofa and a patterned armchair, surrounded by large windows allowing natural light. A coffee table holds magazines and a decorative tray, while plants add a touch of greenery. The kitchenette is visible in the background, enhancing the open layout.

Guesthouse in Bluffton

4.99 out of 5 average rating, 709 reviews

Lowcountry Retreat Carriage House

Located in a quiet neighborhood, minutes from Old Town Bluffton, where you can find unique shops, art galleries, & great places to eat - many with live music! A stroll through the neighborhood will take you past a local park with playground, workout area, & walking paths. There are many ponds to enjoy the local wildlife, wetland areas, and beautiful oak trees. It's so peaceful! Convenient to Hilton Head, Beaufort, and Savannah, it's the perfect spot for exploring, shopping, or relaxing!

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Top Guest favourite

Cottage in Saint Helena Island

4.98 out of 5 average rating, 142 reviews

Private Waterfront Retreat w/ Sauna

Escape to The Hideaway, a newly built modern 2BR/2BA waterfront retreat on St. Helena Island. Surrounded by live oaks and sweeping salt marsh views, this architecturally unique cottage blends luxury and nature with curated amenities, including a private indoor sauna. Peaceful and secluded, yet just minutes from beaches, outdoor adventures, local shops, and dining—designed for rest, reconnection, and renewal.

LocationFamilyLong stay

Top Guest favourite

A tranquil waterfront view is captured at sunset, showcasing vibrant hues of pink and orange reflected across the water. Silhouetted against the sky are tall grasses by the dock, creating a peaceful atmosphere. The scene is framed by a white picket fence.

Guesthouse in Beaufort

4.95 out of 5 average rating, 349 reviews

River Retreat- Waterfront- 1 MI from Parris Islan

This river retreat can sleep 8 and is a little slice of heaven less than a mile from Parris Island. You will have the chance to hopefully see the dolphins feed while you are relaxing or you can sit on the porch and catch a breathtaking sunrise over the water. This is a quiet guest home that has amazing views whether you are coming for a graduation, to relax or enjoy the water this is the spot for you.

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Guest favourite

The villa is set within a lush landscape, featuring a two-story design with a welcoming front porch. Leafy trees provide shade around the well-kept gardens, and a driveway leads to the attached garage, creating an inviting entrance for guests.

Home in Okatie

4.89 out of 5 average rating, 45 reviews

Free Daily Golf Villa · Private Island · 4BR/4BA

Wake up on a private, gated island where your stay includes a round of championship golf EVERY day. Our 4BR/4BA waterfront villa, renovated 2026, has an en-suite bath in every bedroom, sleeps 9, and is dog-friendly. Heated pools, hot tub, tennis, pickleball, spa, and docks included, 25 min from Hilton Head. Monthly snowbird rates available, just ask.

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Superhost

Home in Okatie

5 out of 5 average rating, 4 reviews

Heaven Island Lodge Daily Golf Included

Golfers’Paradise: Free Daily Golf + Comfortable Home. The property is on Callawassie Island and overlooks the 9th fairway of the Palmetto course and is close to Callawassie amenities including golf (two rounds per day included with the daily rental) clubhouse, tennis and pickle ball courts, two pools, kayaks, state of the art fitness center.

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Top Guest favourite

A cozy bedroom features a spacious bed with soft linens, accented by decorative pillows. A stylish wash basin is shown with toiletries on a wooden vanity. A living area showcases comfortable seating, decorative plants, and a coffee table, enhancing the welcoming environment.

Home in Port Royal

4.99 out of 5 average rating, 271 reviews

Great reviews! Stylish Port Royal cottage!

Bright and airy with an open floor plan, this quaint cottage boasts unique features and effortless style in 900 sq. ft. This stylish, newly renovated home is just minutes from Parris Island, historic downtown Beaufort, and a 20-minute scenic drive to Hunting Island-it's the ideal Lowcountry retreat. Port Royal, SC license# 12106

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