Callawassie Island Vacations from $740
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The Latest Callawassie Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- The Galloway House Inn
Aug 27 - Aug 31The Galloway House Inn + Flight
Midtown4 nights4.0 star property9.6/10 - Exceptional (210 reviews)"We love old homes so spending a couple of nights in a beautiful 1890’s home was excellent."Reviewed July 9, 2026Roundtrip • Boston (BOS) - Savannah (SAV)BOS - SAV • Nonstop SAV - BOS • 1 stop$976$740found 2 days agoper traveler - Seawatch at Island Club
Aug 30 - Sep 4Seawatch at Island Club + Flight
Mid Island5 nights3.0 star property9.2/10 - Wonderful (49 reviews)"Great,spacious condo. Beds were comfortable. Plenty of space for family with 2 teens. 2-3 minute walk to the beautiful beach. Nice outdoor grills and corn hole. Pickleball courts were nice."Reviewed July 21, 2026Roundtrip • Chicago (CHI) - Savannah (SAV)MDW - SAV • Nonstop SAV - MDW • Nonstop - Sweetbay by Avantstay 1 Min Walk to Beach + Pool
Sep 27 - Oct 3Sweetbay by Avantstay 1 Min Walk to Beach + Pool + Flight
Mid Island6 nights3.0 star propertyRoundtrip • New York (NYC) - Savannah (SAV)JFK - SAV • Nonstop SAV - JFK • Nonstop - Ocean View at Island Club
Sep 6 - Sep 10Ocean View at Island Club + Flight
Mid Island4 nights3.0 star property8.6/10 - Excellent (14 reviews)"Front desk customer service was awful. The worst"Reviewed May 12, 2026Roundtrip • Boston (BOS) - Savannah (SAV)BOS - SAV • 1 stop SAV - BOS • 1 stop$1,033$785found 23 hours agoper traveler - Sea Pine by Avantstay Private Modern Home Surrounded in Lush Greenery Close to Beach
Oct 1 - Oct 5Sea Pine by Avantstay Private Modern Home Surrounded in Lush Greenery Close to Beach + Flight
Sea Pines4 nights3.5 star property6.0/10 - (1 review)"Great area - Seapine is our favorite place of the island. Overall house was nice but cleaning was subpar -especially outside. Cooking range was very weak- on one of the burner we couldn’t even boil water. They had plenty of laundry detergent, spices and tea- which was very handy. Beach was little bit far- 30 min walking but very scenic walking path."Reviewed August 7, 2025Roundtrip • Boston (BOS) - Savannah (SAV)BOS - SAV • 1 stop SAV - BOS • 1 stop
Callawassie Island Hotel Deals
The Westin Hilton Head Island Resort & Spa
The Westin Hilton Head Island Resort & Spa4.0 star property
13.1 mi from Callawassie Island
8.6 out of 10, Excellent, (1,006 reviews)
8.6/10
Excellent
(1,006 reviews)
"I hate to post a bad review but for those traveling with families as well to be aware— the pool will be overcrowded, with people blasting their own music and making out near kids, the floors near the pool so hot they can burn feet, mystery drink charges from those next to you will end up on your bill, and the front staff lacks professionalism. The bell/valet will be on his phone while “helping” you. The entire hotel needs a revamp. A burger at the pool bar (which also needs a revamp) will cost...
$287 nightly
The price is $316
$316 total
Aug 9 - Aug 10
Total with taxes and fees
Marriott's Barony Beach Club
Marriott's Barony Beach Club3.5 star property
12.9 mi from Callawassie Island
9.4 out of 10, Exceptional, (252 reviews)
9.4/10
Exceptional
(252 reviews)
"I wish we could have stayed longer. Love that we were able to do laundry, although I do wish the water slide was open. My grandchildren would have loved it. We got a villa/suite facing the water park/pool area so my elderly mother could take pictures. 4 generations, what a blessing."
$651 nightly
The price is $716
$716 total
Aug 22 - Aug 23
Total with taxes and fees
Walk to Beach: Hilton Head Condo w/ Pool Access
Walk to Beach: Hilton Head Condo w/ Pool Access3.5 star property
12.8 mi from Callawassie Island
9.6 out of 10, Exceptional, (5 reviews)
9.6/10
Exceptional
(5 reviews)
"Very clean and easy access to the beach "
$346 nightly
The price is $381
$381 total
Aug 4 - Aug 5
Total with taxes and fees
607 Bay Inn Downtown Beaufort
607 Bay Inn Downtown Beaufort2.5 star property
13 mi from Callawassie Island
9.8 out of 10, Exceptional, (122 reviews)
9.8/10
Exceptional
(122 reviews)
"The staff were very helpful and friendly. The room was very nice. The view of the bridge from the front was amazing. The breakfast vouchers were great. Thank you."
$204 nightly
The price is $225
$225 total
Aug 3 - Aug 4
Total with taxes and fees
9.6 out of 10, Exceptional, (850 reviews)
9.6/10
Exceptional
(850 reviews)
"Super close to Downtown, very convenient and walkable. Coffee shop attached was nice as well! Cute place!"
$165 nightly
The price is $182
$182 total
Aug 16 - Aug 17
Total with taxes and fees
The Emerald Boutique Stays
The Emerald Boutique Stays2.5 star property
13.1 mi from Callawassie Island
9.2 out of 10, Wonderful, (269 reviews)
9.2/10
Wonderful
(269 reviews)
"My stay at the Emerald was wonderful! The keypad entries were especially convenient without having to keep up with a key card. I made quite a bit of use of my balcony, which was very enjoyable. The location is extremely convenient to the downtown area. It was overall a very nice day."
$171 nightly
The price is $188
$188 total
Jul 27 - Jul 28
Total with taxes and fees
9.6 out of 10, Exceptional, (178 reviews)
9.6/10
Exceptional
(178 reviews)
"I would stay here again and again. I love the ambiance and charm of the historic home which still shines through along side the luxurious updates in the beautiful bathroom, soft rugs, comfy bed. They have thought of everything and provided a beautiful space to enjoy it in. Games, toiletries, coffee, water, an honor wine bar upstairs. I cannot wait to go back. Full review with video coming to my tiktok @joykapp later today.
I also recommend Old Bull for dinner if you go into town! Friendly...
$193 nightly
The price is $212
$212 total
Jul 28 - Jul 29
Total with taxes and fees
9.0 out of 10, Wonderful, (1,001 reviews)
9.0/10
Wonderful
(1,001 reviews)
"Big room beautiful hotel"
$171 nightly
The price is $188
$188 total
Aug 23 - Aug 24
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.