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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 Francis Marion Hotel

4 out of 5

Price was $819, price is now $612 per person

$612

per person

Nov 11 - Nov 14

found 4 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Charleston (CHS)

Book a stay at this luxury hotel in Charleston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Charleston City Market and South Carolina Aquarium are located nearby.

We enjoyed our stay at the hotel. Staff was very friendly and helpful. we enjoyed the complementary snacks periodically throughout the day. Our only concern was that the beds were it’s too small for two adults.

Reviewed on Aug 26, 2026

The Ryder Hotel

3.5 out of 5

Price was $1,568, price is now $1,097 per person

$1,097

per person

Nov 12 - Nov 15

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.

Summerset by Avantstay Resort Pool + Outdoor Lounge + Firepit + Movie Room IOP Beach Retreat

3 out of 5

Save 100% on your flight

Price was $4,664, price is now $3,325 per person

$3,325

per person

Oct 11 - Oct 16

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

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

Sparrow Haus by Avantstay Luxe Isle of Palms Retreat Pool + Firepit + Outdoor Lounge

3 out of 5

Save 100% on your flight

Price was $4,634, price is now $3,420 per person

$3,420

per person

Oct 12 - Oct 17

found 5 hours ago

Roundtrip flight included

Boston (BOS) to Charleston (CHS)

Stay at this cottage in Isle of Palms. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Isle of Palms Beach and Wild Dunes Resort Golf Course are located nearby.

Planters Inn

4.5 out of 5

Save 100% on your flight

Price was $2,491, price is now $1,861 per person

$1,861

per person

Sep 30 - Oct 4

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 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 $3,524, price is now $2,637 per person

$2,637

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip non-stop 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 $1,019, price is now $778 per person

$778

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip non-stop 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.

Wonderful stay… excellent staff, comfortable room, very conveniently located!

Reviewed on Aug 26, 2026

Water's Edge Inn - Adults Only

3.5 out of 5

Price was $1,081, price is now $832 per person

$832

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop 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.

The stay was amazing here. We had a short stay but surely we would do this again. Would recommend to anyone. Staff is super friendly, area is perfect, perfect room size and bathroom size, etc.

Reviewed on Aug 25, 2026