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
The price is P86,123
P103,326 total
includes taxes & fees
Oct 29 - Oct 30
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
The price is P26,706
P29,377 total
includes taxes & fees
Oct 17 - Oct 18
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
The price is P19,451
P21,396 total
includes taxes & fees
Oct 22 - Oct 23
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
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
The price is P9,180
P27,958 total
includes taxes & fees
Oct 1 - Oct 2
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
The price is P26,956
P29,652 total
includes taxes & fees
Oct 18 - Oct 19
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
The price is P19,451
P21,396 total
includes taxes & fees
Oct 6 - Oct 7
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
The price is P17,950
P19,745 total
includes taxes & fees
Oct 13 - Oct 14
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
The price is P23,266
P25,593 total
includes taxes & fees
Oct 21 - Oct 22
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
The price is P10,632
P26,424 total
includes taxes & fees
Oct 13 - Oct 14
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
The price is P18,513
P20,364 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is P7,255
P22,961 total
includes taxes & fees
Oct 25 - Oct 26
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
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
The price is P5,379
P19,804 total
includes taxes & fees
Oct 9 - Oct 10
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
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
The price is P8,261
P21,718 total
includes taxes & fees
Oct 11 - Oct 12
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
"The hotel was very clean and well maintained. The staff was very pleasant and helpful. The po and beach were great. I would recommend this hotel to all"
Daniel 2-night trip
Posted 1 hour ago
Sonesta Resort Hilton Head Island

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