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Kiawah Island Vacation Packages

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A beach with rows of blue umbrellas and bicycles.

Kiawah Island
South Carolina
United States of America
North America
Hotwire.com

Kiawah Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

The Ryder Hotel

3.5 out of 5

Save 100% on your flight

Price was $1,040, price is now $714 per person

$714

per person

Sep 15 - Sep 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Stay at this hotel in Charleston. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

We had a fantastic stay!

Reviewed on Jul 28, 2026

The Charleston Place

5 out of 5

Save 100% on your flight

Price was $4,398, price is now $3,015 per person

$3,015

per person

Oct 6 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Charleston City Market and Port of Charleston are located nearby.

Great experience from check in to check out.

Reviewed on Jul 29, 2026

Water's Edge Inn - Adults Only

3.5 out of 5

Save 100% on your flight

Price was $1,325, price is now $952 per person

$952

per person

Oct 6 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Stay at this B&B in Folly Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Folly Island Beaches and Folly River Park are located nearby.

Our stay at Water’s Edge Inn was wonderful! The inn is absolutely beautiful, with charming accommodations and a relaxing atmosphere. One of the best features is its convenient location—it’s just a short walk to the beach, pier, and beach access, making it easy to enjoy everything Folly Beach has to offer. The complimentary breakfast each morning was delicious, with a great variety of options to start the day. The bed was incredibly comfortable, and we slept so well. One of our favorite amenities was the complimentary golf cart shuttle. It made getting to Center Street and the pier quick, easy, and fun without having to worry about parking. We thoroughly enjoyed our stay and would absolutely recommend Water’s Edge Inn to anyone looking for a relaxing and convenient getaway at Folly Beach. We can’t wait to come back!

Reviewed on Jul 29, 2026

The Beach Club at Charleston Harbor Resort and Marina

4.5 out of 5

Save 100% on your flight

Price was $2,125, price is now $1,533 per person

$1,533

per person

Oct 6 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this luxury resort in Mount Pleasant. Enjoy free parking, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Patriots Point and USS Yorktown are located nearby.

Our stay was wonderful as always!

Reviewed on Jul 28, 2026

The Pinch Hotel

4 out of 5

Save 100% on your flight

Price was $1,380, price is now $1,007 per person

$1,007

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this spa hotel in Charleston. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Charleston City Market and Port of Charleston are located nearby.

137 Grand Pavilion by Avantstay Steps to Beach + Resort Pools Wild Dunes Gated

3 out of 5

Save 100% on your flight

Price was $3,199, price is now $2,336 per person

$2,336

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Stay at this cottage in Isle of Palms. Enjoy free parking, a beach locale, and balconies. Popular attractions Isle of Palms Beach and Front Beach are located nearby.

1111 Middle Street by Avantstay Charming Historic Cottage Featured in "dear John" Movie Beach Access

3 out of 5

Save 100% on your flight

Price was $3,338, price is now $2,443 per person

$2,443

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this beach cottage in Sullivan's Island. Enjoy free parking, a beach locale, and balconies. Popular attractions Isle of Palms Beach and Sullivan's Island Beach are located nearby.

88 Grand Pavilion Avantstay Near Beach + Pools

3 out of 5

Save 100% on your flight

Price was $3,398, price is now $2,522 per person

$2,522

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Stay at this cottage in Isle of Palms. Enjoy free parking, a beach locale, and balconies. Popular attractions Isle of Palms Beach and Wild Dunes Resort Golf Course are located nearby.