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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.

Shem Creek Inn

3 out of 5

Price was $1,105, price is now $842 per person

$842

per person

Oct 24 - Oct 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Stay at this hotel in Mount Pleasant. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shem Creek Park and Patriots Point are located nearby.

The Ryder Hotel

3.5 out of 5

Save 100% on your flight

Price was $1,679, price is now $924 per person

$924

per person

Oct 24 - Oct 29

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.

712 Ocean Blvd by Avantstay New Construction w/ Pool, Game Zone, Private Beach Access, and Oceanfront Views

3 out of 5

Save 100% on your flight

Price was $9,520, price is now $6,841 per person

$6,841

per person

Oct 24 - Oct 29

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.

The Beach Club at Charleston Harbor Resort and Marina

4.5 out of 5

Save 100% on your flight

Price was $1,418, price is now $1,019 per person

$1,019

per person

Oct 24 - Oct 29

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.

Planters Inn

4.5 out of 5

Save 100% on your flight

Price was $1,432, price is now $1,037 per person

$1,037

per person

Oct 2 - Oct 4

found 1 day ago

Roundtrip non-stop 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 clean rooms in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

Great location! Very clean! Friendly staff! Beautiful room

Reviewed on Aug 22, 2026

Haven by Avantstay Luxury Beachfront Home w/ Pool & Gorgeous Patios

3.5 out of 5

Save 100% on your flight

Price was $3,182, price is now $2,336 per person

$2,336

per person

Oct 24 - Oct 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this beach vacation home in Sullivan's Island. Enjoy free parking, a beach locale, and concierge services. Popular attractions Isle of Palms Beach and Shem Creek Park are located nearby.

Andrew Pinckney Inn

4 out of 5

Save 100% on your flight

Price was $1,657, price is now $1,226 per person

$1,226

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this business-friendly hotel in Charleston. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Charleston City Market and Waterfront Park are located nearby.

We had a wonderful stay! The accommodations were great, the beds were very comfortable, and the staff was friendly and hospitable. The location is perfect, convenient to everything while still being nice and quiet. The extended continental breakfast was fabulous with a great selection each morning. We thoroughly enjoyed our stay and would definitely stay here again!

Reviewed on Aug 21, 2026

The Charleston Place

5 out of 5

Save 100% on your flight

Price was $1,745, price is now $1,329 per person

$1,329

per person

Nov 7 - Nov 11

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 Waterfront Park are located nearby.

The stay was exquisite. We will only stay here going forward. We were the most impressed with the turn down service! Eye glass cloths for our glasses and bookmarks for our books. They went above and beyond the normal turn down with ice, water, slippers and mood lighting. 5 star with the best customer service in the South!

Reviewed on Aug 23, 2026