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

Callawassie Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Callawassie Island vacation rentals

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

1. 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
$1,581 nightly
The price is $1,739
Oct 18 - Oct 19
Total with taxes and fees
Montage Palmetto Bluff Residences
An indoor swimming pool with clear glass ceilings, multiple lounge chairs, and a view of the outdoors.

2. Marriott's Barony Beach Club

Marriott's Barony Beach Club
3.5 star property
Mid Island
9.4 out of 10, Exceptional, (252 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
$427 nightly
The price is $470
Oct 17 - Oct 18
Total with taxes and fees
Marriott's Barony Beach Club
A hotel entrance with a grand staircase, a covered walkway, and a brick-paved area.

3. 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
$311 nightly
The price is $342
Oct 11 - Oct 12
Total with taxes and fees
Marriott's Harbour Club
A waterfront restaurant with outdoor seating and a view of the water.

4. 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
$166 nightly
The price is $183
Oct 7 - Oct 8
Total with taxes and fees
Disney's Hilton Head Island Resort
A beach with a calm sea and a clear sky.

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

Steps to Beach-hilton Head Condo-pet Friendly
2.0 star property
Mid Island
$416 nightly
The price is $458
Oct 1 - Oct 2
Total with taxes and fees
Steps to Beach-hilton Head Condo-pet Friendly
A wooden boardwalk leading to a beach with palm trees and a clear sky.

6. 'wright by the Beach': Hilton Head Condo w/ Perks

'wright by the Beach': Hilton Head Condo w/ Perks
3.0 star property
Mid Island
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay. We loved the ocean theme at the apartment. Very clean rooms. Kids enjoyed swimming in the indoor pool, parents enjoyed hot tub and sauna especially on rainy days. They have indoor and outdoor pools. We liked walking on the boardwalk to the beach. We highly recommend this place and would love to return there again. "
United States
Victor
'wright by the Beach': Hilton Head Condo w/ Perks
A covered outdoor area with a pool, lounge chairs, and a sofa.

7. Marriott's SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (202 reviews)
"Great resort, great room "
United States
Crista
$431 nightly
The price is $474
Oct 18 - Oct 19
Total with taxes and fees
Marriott's SurfWatch
A spacious living area with a high ceiling, large windows, and a central seating arrangement.

8. Marriott's Heritage Club

Marriott's Heritage Club
3.5 star property
Sea Pines
9.4 out of 10, Exceptional, (71 reviews)
"Great Villa! Very roomy and excellent location close to everything!"
United States
Christine
$389 nightly
The price is $428
Oct 1 - Oct 2
Total with taxes and fees
Marriott's Heritage Club
A covered outdoor seating area with a view of the sunset over a body of water.

9. 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, (157 reviews)
"It was a very nice vacation club. They had activities planned throughout the day that you could attend if you’d like. My kids really enjoyed themselves."
United States
Gary T
$287 nightly
The price is $316
Oct 7 - Oct 8
Total with taxes and fees
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
A wooden boardwalk leading to a beach with a bicycle parked on it.

10. 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
$372 nightly
The price is $409
Oct 21 - Oct 22
Total with taxes and fees
Marriott's Monarch at Sea Pines
A living room with a flat-screen TV, a fireplace, a sofa, and a dining area with a table and chairs.

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

Serene Hilton Head Island Condo w/ Community Pool!
4.0 star property
South End
$384 nightly
The price is $422
Oct 11 - Oct 12
Total with taxes and fees
Serene Hilton Head Island Condo w/ Community Pool!
An aerial view of a resort with multiple buildings, a central swimming pool, and a beach in the background.

12. Marriott's Grande Ocean

Marriott's Grande Ocean
3.5 star property
South End
9.4 out of 10, Exceptional, (178 reviews)
"On the ocean. Family friendly."
United States
Richard
$296 nightly
The price is $326
Oct 20 - Oct 21
Total with taxes and fees
Marriott's Grande Ocean
A modern kitchen with granite countertops, a stainless steel sink, and wooden cabinets.

13. Palmetto Dunes Golf Getaway: Pool + Beach Access!

Palmetto Dunes Golf Getaway: Pool + Beach Access!
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (1 review)
"Communication with owner is excellent and villa is located in great location "
United States
minoshka
$334 nightly
The price is $367
Oct 25 - Oct 26
Total with taxes and fees
Palmetto Dunes Golf Getaway: Pool + Beach Access!
A sandy beach with a wooden structure, blue umbrellas, and a clear sky.

14. Oceanfront Breakers 137 Condo w/ Sunrise Views!

Oceanfront Breakers 137 Condo w/ Sunrise Views!
4.0 star property
South End
$383 nightly
The price is $421
Oct 4 - Oct 5
Total with taxes and fees
Oceanfront Breakers 137 Condo w/ Sunrise Views!
A dining area with a wooden table, chairs, and a chandelier. There is a painting on the wall and a cabinet with decorative items.

15. Hilton Head Condo: Beach Supplies, Walk to Shore!

Hilton Head Condo: Beach Supplies, Walk to Shore!
3.0 star property
Mid Island
8.4 out of 10, Very good, (5 reviews)
"I’m thrilled with the location of this condo. It’s just a quick walk to the beach, and there are also easy-to-access walking, running, and biking trails. There are plenty of local restaurants, food trucks, grocery stores, and attractions nearby. The only downside is that I didn’t receive the email from Evolve with the check-in/out instructions, as it was delivered to my spam folder. The unit was a bit dusty, probably because it was the off-season when I visited, but a quick trip to the local...
United States
Derval
$288 nightly
The price is $317
Oct 9 - Oct 10
Total with taxes and fees
Hilton Head Condo: Beach Supplies, Walk to Shore!
A modern living room with a glass coffee table, a sofa, a white nightstand, and a large mirror.

16. Beachfront Condo w/ Pool Access in Hilton Head!

Beachfront Condo w/ Pool Access in Hilton Head!
4.0 star property
South End
8.0 out of 10, Very good, (3 reviews)
"The security guard was friendly. The condo was clean. I am not sure if all of these were from the host or left behind but there was a coffee maker, spice rack (which I’ve never seen in a condo before), dishwasher, plenty of pots and pans, not a lot of utensils for cooking, a hair dryer, small tin of coffee creamer, pool towel (clean), extra blankets (clean), a single trash bag for the kitchen, paper towels, kitchen towel, chairs and beach things on the deck. It was on the beach just have to walk...
United States
Manuel
$351 nightly
The price is $386
Oct 21 - Oct 22
Total with taxes and fees
Beachfront Condo w/ Pool Access in Hilton Head!
A sandy beach with tall grasses in the foreground and a clear blue sky.

17. Oceanfront Hilton Head Island Condo w/ Pool!

Oceanfront Hilton Head Island Condo w/ Pool!
3.0 star property
South End
8.8 out of 10, Excellent, (6 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
$316 nightly
The price is $347
Oct 11 - Oct 12
Total with taxes and fees
Oceanfront Hilton Head Island Condo w/ Pool!
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

Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

10/10 Excellent
"We enjoyed our vacation at Sonesta. The staff was super nice and helpful, the place is clean and spacious. Out of the three nights they semi-cleaned our room once, but they did replenish the towels daily. I loved the location, pool, beach and trails. My toddler raves about the turtle feeding & the smores. I actually liked that there was a 18+ only pool, is nice to know if kids get annoying or loud the adults that just want peace can go there. The only thing we didn’t enjoy was the food, not great and super overpriced. We ordered to go be there was still a big service fee, we ended up door dashing from outside and that was considerably cheaper and better."
Priscila 3-night trip
Posted 6 hours ago
Sonesta Resort Hilton Head Island

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 $316 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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