Callawassie Island Holiday Rentals

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Our top choices for Callawassie Island holiday rentals

Condo resort in Mid Island

Marriott's Barony Beach Club
3.5 star property
9.6 out of 10, Exceptional, (243)
"Great place for vacation on the beach, nice, clean and quiet areas "
United States
Larisa
The price is AU$305
includes taxes & fees
5 Jan - 6 Jan 2026
Marriott's Barony Beach Club

Holiday Home in Sea Pines

Marriott's Harbour Club
3.5 star property
9.2 out of 10, Wonderful, (61)
"The staff was extremely inviting, professional, and kind. Parking was extremely easy we stayed in villa 3939. It was very large, clean, and had a great view. The property was conveniently located within the area and very walkable. It is very dark at night but we felt safe walking back from dinner. I’d definitely recommend this property for a quiet and peaceful getaway."
United States
ANGELEE
The price is AU$334
includes taxes & fees
1 Jan - 2 Jan 2026
Marriott's Harbour Club
2.0 star property
8.0 out of 10, Very good, (2)
"No proper communication and things broke inside or not working "
United States
Alejandra
The price is AU$459
includes taxes & fees
4 Jan - 5 Jan 2026
Beach Getaway 2BR w/ Pool + Modern Comforts
3.5 star property
8.6 out of 10, Excellent, (98)
"It was perfect for our needs. Check-in was super easy!"
United States
Melanie
Ocean Palms Villas at Port Royal Resort

Holiday Home in Mid Island

Disney's Hilton Head Island Resort
3.5 star property
9.6 out of 10, Exceptional, (127)
"While the rooms are overdue a refurbishment, this place is a wondeful resort. "
United States
Chad
Disney's Hilton Head Island Resort

Holiday Home in Palmetto Bluff

Montage Palmetto Bluff Residences
5.0 star property
10.0 out of 10, Exceptional, (1)
"This was our second visit to Montage Palmetto Bluff and once again it did not disappoint. The hospitality we find here is second to none. Everywhere we went we were greeted with smiling faces. We’d like to give a special shout out to Carmela at the concierge desk who was so incredibly wonderful with our 4 year-old son, Henry. Everything she did and every recommendation she provided enhanced our stay. The natural beauty of this place is beyond compare. We cannot wait to visit again. "
United States
Ashley
The price is AU$2,350
includes taxes & fees
10 Jan - 11 Jan 2026
Montage Palmetto Bluff Residences

Aparthotel in South End

Players Club Resort
4.0 star property
8.0 out of 10, Very good, (10)
"Clean, safe, and relaxing location. Enjoyed the beach and local restaurants. "
United States
Melvin
The price is AU$343
includes taxes & fees
30 Dec - 31 Dec
Players Club Resort

Condo resort in South End

Marriott's Grande Ocean
3.5 star property
9.4 out of 10, Exceptional, (164)
"Great room and amenities. Unfortunately, we had a poor experience with the front desk at checkout. Took 5 stars directly to 3 . "
United States
Patrick
The price is AU$346
includes taxes & fees
5 Jan - 6 Jan 2026
Marriott's Grande Ocean

Holiday Home in Sea Pines

Marriott's Heritage Club
3.5 star property
9.4 out of 10, Exceptional, (67)
"Another great Marriott, super clean and spacious with the comforts we needed to finish out a long trip (e.g. hot tub, laundry, kitchen). Friendly staff and convenient to the forest reserve."
United States
Landry
The price is AU$267
includes taxes & fees
7 Jan - 8 Jan 2026
Marriott's Heritage Club
2.0 star property
The price is AU$473
includes taxes & fees
4 Jan - 5 Jan 2026
Spacious 3BR Hilton Head Getaway + Pool Access
3.0 star property
9.2 out of 10, Wonderful, (129)
"Great stay "
United States
Ashalon
The price is AU$260
includes taxes & fees
8 Jan - 9 Jan 2026
Marriott's Monarch at Sea Pines
2.0 star property
The price is AU$480
includes taxes & fees
30 Dec - 31 Dec
Hilton Head 2BR Escape w/ Pool & Sofa Bed
2.0 star property
The price is AU$474
includes taxes & fees
4 Jan - 5 Jan 2026
Renovated 2BR Hilton Head Home Walk to Shops
2.0 star property
The price is AU$467
includes taxes & fees
4 Jan - 5 Jan 2026
Family 2BR Retreat Near Beach + Pool Hilton Head
2.0 star property
The price is AU$455
includes taxes & fees
5 Jan - 6 Jan 2026
Family-friendly 2BR Home w/ Sofa Bed Hilton Head
2.0 star property
The price is AU$460
includes taxes & fees
13 Jan - 14 Jan 2026
Stylish 2BR Townhome Near Bradley Beach + Pool
2.0 star property
The price is AU$456
includes taxes & fees
30 Dec - 31 Dec
Central Hilton Head Retreat 2BR Near Beaches
2.0 star property
The price is AU$401
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Head 3BR Retreat Pool, Dining & Shops
2.0 star property
2.0 out of 10, (1)
"The place smelled really bad like cigarettes. Go into the bathroom and it smelled like sewage. Rugs were filthy black dirt on our feet. Queen size bed right in the living room behind the tv."
United States
Ava
The price is AU$463
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy 2BR Hilton Head Townhome w/ Pool Access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Callawassie Island Hotel Reviews

Find out more about Callawassie Island

Everything you need to know about Callawassie Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Callawassie Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Callawassie Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Callawassie Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Callawassie Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Callawassie Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Callawassie Island holiday rentals we have selected for you start as low as AU$260 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Callawassie Island rentals

At Expedia, we put the best Callawassie Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Callawassie Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Callawassie Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Callawassie Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.