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

Callawassie Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Callawassie Island vacation rentals

1. Lux|King Bed|Free Golf|Heated Pool|Bikes|Parris Is

Lux|King Bed|Free Golf|Heated Pool|Bikes|Parris Is
Okatie
The price is CA $519
CA $1,156 total
includes taxes & fees
Nov 2 - Nov 3
Lux|King Bed|Free Golf|Heated Pool|Bikes|Parris Is

2. 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 CA $525
CA $577 total
includes taxes & fees
Nov 1 - Nov 2
Marriott's SurfWatch

3. 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 CA $447
CA $491 total
includes taxes & fees
Nov 1 - Nov 2
Marriott's Heritage Club

4. Carriage House within 5 minute walk of Old Town Bluffton

Carriage House within 5 minute walk of Old Town Bluffton
Old Town Bluffton
10.0 out of 10, Exceptional, (95 reviews)
"Very clean, and very convenient location. Host was great and communicated perfectly. We will definitely stay again."
United States
Derek
The price is CA $160
CA $398 total
includes taxes & fees
Oct 15 - Oct 16
Carriage House within 5 minute walk of Old Town Bluffton

5. C & N Lodging, Bluffton, SC

C & N Lodging, Bluffton, SC
Bluffton
9.8 out of 10, Exceptional, (11 reviews)
"Great place to stay. Charming decor, comfortable bed. Great communication with host. "
United States
Erika H.
The price is CA $179
CA $332 total
includes taxes & fees
Oct 4 - Oct 5
C & N Lodging, Bluffton, SC

6. Sweet Nest Bluffton Cottage • Fenced in yard • Pet-Friendly • Gazebo • Private

Sweet Nest Bluffton Cottage • Fenced in yard • Pet-Friendly • Gazebo • Private
Bluffton
9.0 out of 10, Wonderful, (17 reviews)
"Perfect spot, beautifully appointed, comfortable and private. Perfect for traveling with pet"
United States
andrea R.
The price is CA $233
CA $377 total
includes taxes & fees
Oct 4 - Oct 5
Sweet Nest Bluffton Cottage • Fenced in yard • Pet-Friendly • Gazebo • Private

7. Old Town Bluffton Cottage | Pet-Friendly, Big Yard

Old Town Bluffton Cottage | Pet-Friendly, Big Yard
Old Town Bluffton
9.4 out of 10, Exceptional, (146 reviews)
"This is a perfect little long weekend get away retreat! Very clean, close to everything walking distance to shops restaurants the river and parks. The bed was extremely comfortable. We were in town for a family reunion and had family that were staying close by it was the perfect spot to gather a visit. We will definitely book again next year for the union."
United States
Eric
The price is CA $192
CA $468 total
includes taxes & fees
Oct 6 - Oct 7
Old Town Bluffton Cottage | Pet-Friendly, Big Yard

8. GOLF CART! Remodeled home near Old Town, Xbox!

GOLF CART! Remodeled home near Old Town, Xbox!
Bluffton
10.0 out of 10, Exceptional, (41 reviews)
"House is beautiful, clean and very comfortable. Location is great - close to restaurants and stores. Really enjoyed our stay and will recommend it to family and friends."
United States
Steven F.
The price is CA $372
CA $765 total
includes taxes & fees
Oct 9 - Oct 10
GOLF CART! Remodeled home near Old Town, Xbox!

9. Old Town + Walk to restaurant + EV Charger

Old Town + Walk to restaurant + EV Charger
Old Town Bluffton
9.8 out of 10, Exceptional, (30 reviews)
"Great location!"
United States
T C.
The price is CA $198
CA $534 total
includes taxes & fees
Oct 5 - Oct 6
Old Town + Walk to restaurant + EV Charger

10. The Bluffton Farmhouse

The Bluffton Farmhouse
Bluffton
10.0 out of 10, Exceptional, (124 reviews)
"Great location, close to everything"
United States
Kerry L.
The price is CA $288
CA $628 total
includes taxes & fees
Oct 4 - Oct 5
The Bluffton Farmhouse

11. 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

12. 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 CA $464
CA $510 total
includes taxes & fees
Nov 2 - Nov 3
Marriott's Monarch at Sea Pines

13. Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!

Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!
Old Town Bluffton
9.8 out of 10, Exceptional, (97 reviews)
"Excellent location, very clean, will definitely repeat"
United States
Sean m.
The price is CA $294
CA $734 total
includes taxes & fees
Oct 5 - Oct 6
Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!

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

Beachfront Condo w/ Pool Access in Hilton Head!
South End
9.2 out of 10, Wonderful, (94 reviews)
"Ocean view was great! The pool was well maintained, warm and with a good amount of chairs. Super close to Coligny beach and shops! Loved our time there and will be back! "
United States
Gary B.
The price is CA $101
CA $557 total
includes taxes & fees
Oct 21 - Oct 22
Beachfront Condo w/ Pool Access in Hilton Head!

15. Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116
Mid Island
9.6 out of 10, Exceptional, (116 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
The price is CA $70
CA $472 total
includes taxes & fees
Oct 10 - Oct 11
Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

16. Charming Coastal Casa on Beaufort's Battery Creek

Charming Coastal Casa on Beaufort's Battery Creek
Beaufort
9.8 out of 10, Exceptional, (53 reviews)
"The view was worth it, peaceful"
United States
Amanda
The price is CA $135
CA $296 total
includes taxes & fees
Oct 5 - Oct 6
Charming Coastal Casa on Beaufort's Battery Creek

17. Gorgeous Waterfront Battery Creek Retreat

Gorgeous Waterfront Battery Creek Retreat
Beaufort
10.0 out of 10, Exceptional, (122 reviews)
"The location was lovely and made for the perfect getaway. "
United States
Jim S.
The price is CA $135
CA $294 total
includes taxes & fees
Oct 4 - Oct 5
Gorgeous Waterfront Battery Creek Retreat

18. At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.

At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.
Mid Island
10.0 out of 10, Exceptional, (155 reviews)
"Cozy condo that was perfect for our stay."
United States
Shawn K.
The price is CA $125
CA $372 total
includes taxes & fees
Oct 26 - Oct 27
At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.

19. Ocean View Condo - Perfect location! 2 BR 2 BA

Ocean View Condo - Perfect location! 2 BR 2 BA
Mid Island
9.8 out of 10, Exceptional, (104 reviews)
"Great location and amazing view! We loved our stay!"
United States
Elizabeth K.
The price is CA $216
CA $540 total
includes taxes & fees
Oct 6 - Oct 7
Ocean View Condo - Perfect location! 2 BR 2 BA

20. Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included
South End
9.8 out of 10, Exceptional, (31 reviews)
"Excellent location! The place was so close to the beach & walking/biking distance to shops and restaurants."
United States
Kathleen
The price is CA $147
CA $408 total
includes taxes & fees
Oct 10 - Oct 11
Beach Daze-Gorgeous new shower! Bikes Included
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Callawassie Island Hotel Reviews

Find out more about Callawassie Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Callawassie Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia