A crescent moon rises over a river in the low country of South Carolina with the marsh and a boat dock in silhouette; copy space; blue hour; twilight

Callawassie Island Vacation Rentals

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Our top choices for Callawassie Island vacation rentals

Montage Palmetto Bluff Residences

Montage Palmetto Bluff Residences
5.0 star property
Palmetto Bluff
10.0 out of 10, Exceptional, (2 reviews)
"Very family friendly. Parking was a problem Check in was not one minute early. House was beautiful and very clean. Pool was wonderful Prices were high but we knew that ahead of time"
United States
john j
$1,459 nightly
The price is $1,605
Jul 12 - Jul 13
Total with taxes and fees
Montage Palmetto Bluff Residences

Fire Pit + Yard: Charming Port Royal Home!

Fire Pit + Yard: Charming Port Royal Home!
3.0 star property
Port Royal
10.0 out of 10, Exceptional, (9 reviews)
"A great place to stay. The property was well laid out and the reservation and check in process was hassle free."
United States
Rob
$303 nightly
The price is $333
Jul 8 - Jul 9
Total with taxes and fees
Fire Pit + Yard: Charming Port Royal Home!

Disney's Hilton Head Island Resort

Disney's Hilton Head Island Resort
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (131 reviews)
"The room and property were incredible! Already booking my next stay"
United States
Melissa
$509 nightly
The price is $560
Jun 15 - Jun 16
Total with taxes and fees
Disney's Hilton Head Island Resort

Marriott's Harbour Club

Marriott's Harbour Club
3.5 star property
Sea Pines
9.0 out of 10, Wonderful, (63 reviews)
"Clean and spacious. Very convenient location. "
United States
CLAUDIA
$439 nightly
The price is $483
Jul 8 - Jul 9
Total with taxes and fees
Marriott's Harbour Club

Marriott's Barony Beach Club

Marriott's Barony Beach Club
3.5 star property
Mid Island
9.4 out of 10, Exceptional, (250 reviews)
"Family orientated hotel with great pools, walk on beach access, wonderful BBQ options for self catering. Rooms are large and family orientated. Fab stay! "
Australia
Pauline
$1,044 nightly
The price is $1,148
Jun 15 - Jun 16
Total with taxes and fees
Marriott's Barony Beach Club

Pool Time & Island Vibes! Hilton Head Getaway

Pool Time & Island Vibes! Hilton Head Getaway
3.0 star property
Mid Island
$388 nightly
The price is $427
Jun 14 - Jun 15
Total with taxes and fees
Pool Time & Island Vibes! Hilton Head Getaway

Marriott's Heritage Club

Marriott's Heritage Club
3.5 star property
Sea Pines
9.4 out of 10, Exceptional, (67 reviews)
"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
$399 nightly
The price is $439
Jun 21 - Jun 22
Total with taxes and fees
Marriott's Heritage Club

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Marriott's Harbour Point and Sunset Pointe at Shelter Cove
3.5 star property
Mid Island
9.2 out of 10, Wonderful, (153 reviews)
"Very nice place to stay "
United States
Alejandro
$423 nightly
The price is $465
Jun 21 - Jun 22
Total with taxes and fees
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Marriott's SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (199 reviews)
"Great resort, great room "
United States
Crista
$1,049 nightly
The price is $1,154
Jun 13 - Jun 14
Total with taxes and fees
Marriott's SurfWatch

1 Mi to River! Relaxing Family Home in Bluffton

1 Mi to River! Relaxing Family Home in Bluffton
3.0 star property
Bluffton
$630 nightly
The price is $692
Jul 5 - Jul 6
Total with taxes and fees
1 Mi to River! Relaxing Family Home in Bluffton

Marriott's Grande Ocean

Marriott's Grande Ocean
3.5 star property
South End
9.4 out of 10, Exceptional, (174 reviews)
"Very clean room, warm pools, excellent location! "
United States
Sean
$851 nightly
The price is $936
Jul 6 - Jul 7
Total with taxes and fees
Marriott's Grande Ocean

Charming Bluffton Home w/ Yard ~ 3 Mi to Beaches!

Charming Bluffton Home w/ Yard ~ 3 Mi to Beaches!
3.0 star property
Bluffton
$622 nightly
The price is $684
Jun 23 - Jun 24
Total with taxes and fees
Charming Bluffton Home w/ Yard ~ 3 Mi to Beaches!

Marriott's Monarch at Sea Pines

Marriott's Monarch at Sea Pines
3.0 star property
Sea Pines
9.2 out of 10, Wonderful, (132 reviews)
"Loved this property "
United States
Sharon
$724 nightly
The price is $796
Jun 13 - Jun 14
Total with taxes and fees
Marriott's Monarch at Sea Pines

Oceanfront Breakers 137 Condo w/ Sunrise Views!

Oceanfront Breakers 137 Condo w/ Sunrise Views!
3.5 star property
South End
$382 nightly
The price is $420
Jun 21 - Jun 22
Total with taxes and fees
Oceanfront Breakers 137 Condo w/ Sunrise Views!

Walk to Beach: Hilton Head Condo w/ Pool Access

Walk to Beach: Hilton Head Condo w/ Pool Access
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (5 reviews)
"Very clean and easy access to the beach "
United States
LUMINITA
$402 nightly
The price is $443
Jul 6 - Jul 7
Total with taxes and fees
Walk to Beach: Hilton Head Condo w/ Pool Access

Oceanfront Condo! Breakers 210 w/ Sunrise Views

Oceanfront Condo! Breakers 210 w/ Sunrise Views
3.5 star property
South End
$468 nightly
The price is $515
Jul 9 - Jul 10
Total with taxes and fees
Oceanfront Condo! Breakers 210 w/ Sunrise Views

Oceanfront Hilton Head Island Condo w/ Pool!

Oceanfront Hilton Head Island Condo w/ Pool!
3.0 star property
South End
9.0 out of 10, Wonderful, (4 reviews)
"Nice!! Location great, easy instructions on entry access, nice side view of the ocean from the balcony, the host Meagan was so very nice and accommodating, very close to restaurants and stores, would love to stay here again, Thanks a million!!!! ;)"
United States
Beverly
$341 nightly
The price is $375
Jun 14 - Jun 15
Total with taxes and fees
Oceanfront Hilton Head Island Condo w/ Pool!

Pools, Beach Access: South Carolina Retreat!

Pools, Beach Access: South Carolina Retreat!
3.0 star property
Mid Island
8.0 out of 10, Very Good, (7 reviews)
"Absolutely loved and enjoyed staying here. Was a clean and very enjoyable experience. Just as described. Will definitely recommend and would love to be back. Thank you "
United States
Laura
$310 nightly
The price is $341
Jun 21 - Jun 22
Total with taxes and fees
Pools, Beach Access: South Carolina Retreat!

Serene Hilton Head Island Condo w/ Community Pool!

Serene Hilton Head Island Condo w/ Community Pool!
4.0 star property
South End
$395 nightly
The price is $434
Jun 17 - Jun 18
Total with taxes and fees
Serene Hilton Head Island Condo w/ Community Pool!

Beach Access: Oceanfront Hilton Head Studio

Beach Access: Oceanfront Hilton Head Studio
3.0 star property
South End
8.0 out of 10, Very Good, (2 reviews)
"After a couple of bumps resolved, our stay was very good. Location is great also. We would definitely stay here again. Thanks to the owner and his hospitality crew."
United States
Marvin
$316 nightly
The price is $348
Jun 13 - Jun 14
Total with taxes and fees
Beach Access: Oceanfront Hilton Head Studio
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Callawassie Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Callawassie Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Callawassie Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $290 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Callawassie Island rentals

At Expedia, we put the best Callawassie Island vacation 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 vacation.

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.

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