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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 $970, price is now $708 per person

$708

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip 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.

The Ryder Hotel

3.5 out of 5

Save 100% on your flight

Price was $1,677, price is now $1,102 per person

$1,102

per person

Oct 23 - Oct 26

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 $4,672, price is now $3,330 per person

$3,330

per person

Oct 11 - Oct 16

found 19 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.

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

3.5 out of 5

Save 100% on your flight

Price was $7,243, price is now $5,207 per person

$5,207

per person

Oct 6 - Oct 13

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.

The Charleston Place

5 out of 5

Save 100% on your flight

Price was $3,109, price is now $2,327 per person

$2,327

per person

Nov 12 - Nov 16

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.

Sea Shell by Avantstay Breezy Beachside Getaway w/ Rooftop Deck & 6 BRs

3.5 out of 5

Save 100% on your flight

Price was $3,284, price is now $2,465 per person

$2,465

per person

Sep 20 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Charleston (CHS)

Book a stay at this business-friendly vacation home in Isle of Palms. Enjoy free parking, concierge services, and balconies. Popular attractions Isle of Palms Beach and Sullivan's Island Beach are located nearby.

Planters Inn

4.5 out of 5

Save 100% on your flight

Price was $1,725, price is now $1,298 per person

$1,298

per person

Oct 12 - Oct 16

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.

Planters Inn is a refined hotel with wonderful amenities and a great value

Reviewed on Aug 15, 2026

2701 Palm Boulevard by Avantstay Steps to the Beach, Ping Pong, Putting Green

3 out of 5

Save 100% on your flight

Price was $4,345, price is now $3,311 per person

$3,311

per person

Sep 27 - Oct 3

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Charleston (CHS)

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