A sunset over a lake with a dock and distant trees silhouetted against the sky.

Callawassie Island Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Callawassie Island vacation rentals

A covered outdoor area with a pool, lounge chairs, and a sofa.

1. Marriott's SurfWatch

Mid Island

Crista

₩292,855 total

includes taxes & fees

Nov 30 - Dec 1

A historic building with a covered porch and a brick pathway.

2. Montage Palmetto Bluff Residences

Palmetto Bluff

john j

₩2,449,699 total

includes taxes & fees

Nov 15 - Nov 16

A spacious living area with a high ceiling, large windows, and a central seating arrangement.

3. Marriott's Heritage Club

Sea Pines

Christine

₩217,764 total

includes taxes & fees

Dec 2 - Dec 3

A waterfront restaurant with outdoor seating and a view of the water.

4. Disney's Hilton Head Island Resort

Mid Island

Melissa

A wooden boardwalk leading to a building surrounded by dense greenery.

5. Steps to Beach-hilton Head Condo-pet Friendly

Mid Island

Robert

₩599,415 total

includes taxes & fees

Nov 12 - Nov 13

A sandy beach with tall grasses in the foreground and a clear blue sky.

6. Oceanfront Hilton Head Island Condo w/ Pool!

South End

Beverly

₩409,232 total

includes taxes & fees

Nov 9 - Nov 10

A dining area with a wooden table, chairs, a chandelier, and a painting on the wall.

7. Hilton Head 2BR Townhouse Walk to Shops & Dining

Mid Island

₩435,255 total

includes taxes & fees

Dec 8 - Dec 9

An indoor swimming pool with clear glass ceilings, multiple lounge chairs, and a view of the outdoors.

8. Marriott's Barony Beach Club

Mid Island

Larisa

₩279,338 total

includes taxes & fees

Dec 1 - Dec 2

A wooden boardwalk leading to a beach with a bicycle parked on it.

9. Marriott's Monarch at Sea Pines

Sea Pines

Cory

₩333,403 total

includes taxes & fees

Nov 19 - Nov 20

A covered outdoor seating area with a view of the sunset over a body of water.

10. Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Mid Island

Gary T

₩130,659 total

includes taxes & fees

Nov 30 - Dec 1

A hotel entrance with a grand staircase, a covered walkway, and a brick-paved area.

11. Marriott's Harbour Club

Sea Pines

Mark

₩163,699 total

includes taxes & fees

Dec 6 - Dec 7

An aerial view of a resort with multiple buildings, a central swimming pool, and a beach in the background.

12. Marriott's Grande Ocean

South End

Robert Alan

₩324,393 total

includes taxes & fees

Nov 30 - Dec 1

A sandy beach with a wooden structure, blue umbrellas, and a clear sky.

13. Oceanfront Breakers 137 Condo w/ Sunrise Views!

South End

Ron

₩565,421 total

includes taxes & fees

Nov 11 - Nov 12

A living room with a flat-screen TV, a fireplace, a sofa, and a dining area with a table and chairs.

14. Serene Hilton Head Island Condo w/ Community Pool!

South End

₩518,237 total

includes taxes & fees

Nov 9 - Nov 10

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Find vacation rentals that suit your style

Top Callawassie Island Hotel Reviews

A Holiday Inn Express hotel with a covered entrance, columns, and a well-lit facade.

Holiday Inn Express Bluffton at Hilton Head Area by IHG

Bluffton

10/10 Excellent

Bill

A modern interior with a curved staircase, white railings, and a round table.

Hilton Garden Inn Hilton Head

Moss Creek

10/10 Excellent

Here now. Mini suite is larger than expected, very clean but noise from AC was loud at times. Staff was great. Very clean. Unfortunately it rained so we didn’t get to use the pool but it was pretty clean and decent size. Nice outdoor deck to have breakfast on when its not raining. Definitely would stay here again. Really close to the outlets. Gas station within walking distance. Breakfast buffet was a good option for convenience but nothing special. Waitress was very nice. Over all it was a...

Antoinette

A hotel lobby with a long dining table, multiple chairs, a sofa, and a television on the wall.

Hampton Inn & Suites Bluffton-Sun City

Bluffton

10/10 Excellent

Arrived earlier than expected and was allowed to check in a little early, which was great. Staff was very friendly and helpful. Was pleased with the room, and the bed was very comfortable. The room looked clean and smelled fresh, and it wasn't until I was getting ready for bed that I pulled the spread down and found 2 candy bar wrappers on the floor up next to the bottom of the bed. Although the rest of the room had been fine, this led me to believe that the room hadn't been cleaned as it should...

Tina

A hotel room with a bed, a desk, a chair, a small table, a TV mounted on the wall, and a window with curtains.

Palmera Inn and Suites

South End

10/10 Excellent

Shaneke

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Mid Island

10/10 Excellent

Me and my family live about 2 1/2 hours away from HHI, so we come to this beautiful island several times a year. We've stayed at many different hotels during our past visits. I MUST say that this hotel was by far the nicest we've every stayed in. The cleanliness was just unbelievable. The Location was prefect. Our room faced the river and marsh, the seen was amazing. My wife didn't won't to leave. I would recommend this hotel to everyone no matter your age or family size.

Robert

A view through large windows of a landscaped garden with a circular stone feature, surrounded by potted plants.

Montage Palmetto Bluff

Palmetto Bluff

10/10 Excellent

We visited Montage bluffton couple of days ago. We cannot describe how delighted we were from the moment we reached the hotel till we left. We were greeted at the gate and were given a cd to tell us more about bluffton history on our way to the hotel grounds. Once we reached the hotel a wonderful team greeted us. The receptionist gave my 2 year old stuffed animals that she loved. The room was nice with a spacious bathroom, consideration to little details was obvious, like umbrellas, bath...

al qudah family

A modern kitchen with a built-in island, a flat-screen TV, and a coffee station.

Best Western Sea Island Inn

Historic District

10/10 Excellent

Brooke

A modern kitchen with wooden flooring, pendant lighting, and a coffee station.

Extended Stay America Premier Suites Bluffton Hilton Head

Bluffton

10/10 Excellent

Nathan

An outdoor dining area with a view of the beach, string lights, and palm trees.

Omni Hilton Head Oceanfront Resort

Mid Island

10/10 Excellent

Milan

A modern hotel building with a prominent 'tru by Hilton' sign, large windows, and a parking lot.

Tru by Hilton Beaufort, SC

Beaufort

10/10 Excellent

Jennifer

Marriott's Harbour Club

Sea Pines

10/10 Excellent

Nicole

Circa 1785

Historic District

10/10 Excellent

Ethan

Marriott's Heritage Club

Sea Pines

10/10 Excellent

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Find out more about Callawassie Island

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Callawassie Island Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Callawassie Island vacation rentals

1. Marriott's SurfWatch

2. Montage Palmetto Bluff Residences

3. Marriott's Heritage Club

4. Disney's Hilton Head Island Resort

5. Steps to Beach-hilton Head Condo-pet Friendly

6. Oceanfront Hilton Head Island Condo w/ Pool!

7. Hilton Head 2BR Townhouse Walk to Shops & Dining

8. Marriott's Barony Beach Club

9. Marriott's Monarch at Sea Pines

10. Marriott's Harbour Point and Sunset Pointe at Shelter Cove

11. Marriott's Harbour Club

12. Marriott's Grande Ocean

13. Oceanfront Breakers 137 Condo w/ Sunrise Views!

14. Serene Hilton Head Island Condo w/ Community Pool!

Find vacation rentals that suit your style

Top Callawassie Island Hotel Reviews

Holiday Inn Express Bluffton at Hilton Head Area by IHG

10/10 Excellent

Find out more about Callawassie Island

Explore a world of travel with Expedia