Search Deals onKiawah Island Vacation Packages
Kiawah Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Ryder Hotel
Save 100% on your flight
Price was $2,177, price is now $1,393 per person
$1,393
per person
Sep 24 - Sep 30
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
Save 100% on your flight
Price was $6,201, price is now $4,359 per person
$4,359
per person
Sep 16 - Sep 22
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Front Beach are located nearby.
Haven by Avantstay Luxury Beachfront Home w/ Pool & Gorgeous Patios
Save 100% on your flight
Price was $8,985, price is now $6,339 per person
$6,339
per person
Oct 6 - Oct 13
found 15 hours 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 Sullivan's Island Beach are located nearby.
The Pinch Hotel
Save 100% on your flight
Price was $2,285, price is now $1,640 per person
$1,640
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip 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.
913 Carolina Boulevard by Avantstay Private Pool, Ocean View, Rooftop
Save 100% on your flight
Price was $8,269, price is now $5,972 per person
$5,972
per person
Oct 6 - Oct 13
found 15 hours ago
Roundtrip flight included
Boston (BOS) 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 Front Beach are located nearby.
Planters Inn
Save 100% on your flight
Price was $2,323, price is now $1,678 per person
$1,678
per person
Sep 24 - Sep 30
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 central location. Very charming property. Nice room. Clean bathroom. Friendly and helpful staff. We will definitely stay again when we return to Charleston.
Reviewed on Jul 30, 2026
Lighthouse by Avantstay Beachfront View Home w/ Pool Table & Ping Pong
Save 100% on your flight
Price was $10,059, price is now $7,273 per person
$7,273
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Book a stay at this beach cottage in Folly Beach. Enjoy free parking, a beach locale, and concierge services. Popular attractions Folly Island Beaches and Folly River Park are located nearby.
Southern Oasis by Avantstay 0.5mi Walk to the Beach, Pool, Patio, Large Yard
Save 100% on your flight
Price was $5,730, price is now $4,162 per person
$4,162
per person
Oct 6 - Oct 13
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Charleston (CHS)
Stay at this cottage in Isle of Palms. Enjoy free parking, a beach locale, and patios. Popular attractions Isle of Palms Beach and Front Beach are located nearby.
Kiawah Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Kiawah Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Sep 11 - Fri, Sep 11
BDL
Bradley Intl.
CHS
Charleston Intl.
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Wed, Aug 19 - Tue, Aug 25
DCA
Ronald Reagan Washington National
CHS
Charleston Intl.
$202 Roundtrip, found 6 hours ago
$202
Roundtrip
found 6 hours ago
Tue, Oct 6 - Tue, Oct 6
ORD
O'Hare Intl.
CHS
Charleston Intl.
$203 Roundtrip, found 3 days ago
$203
Roundtrip
found 3 days ago
Mon, Sep 7 - Fri, Sep 11
SWF
Stewart Intl.
CHS
Charleston Intl.
$205 Roundtrip, found 5 days ago
$205
Roundtrip
found 5 days ago
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