Callawassie Island Vacation Packages 2026 from $607

Callawassie Island flight + hotel vacation packages

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

Seawatch at Island Club

Mid Island

Save 100% on your flight

$607

per person

Aug 12 - Aug 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

This condo features a gym and a seasonal outdoor pool. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. Enjoy the sauna and perks like free self parking and free WiFi.

Ocean View at Island Club

Mid Island

Save 100% on your flight

$857

per person

Jun 27 - Jul 2

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

This condo features an outdoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

River Street Inn

Historic Downtown Savannah

Save 100% on your flight

$742

per person

Jul 1 - Jul 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

This luxury hotel's 3 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.

JW Marriott Savannah Plant Riverside District

Historic Downtown Savannah

Save 100% on your flight

$801

per person

Jul 1 - Jul 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

A full-service spa, 12 restaurants, and a 24-hour gym are all featured at this luxury hotel. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi. Relax with a drink at one of the 3 bars/lounges and enjoy the a rooftop terrace.

2 Units w/ Free Parking Walkable Historic District The Juliette by Avantstay

Historic Downtown Savannah

Save 100% on your flight

$2,055

per person

Jun 27 - Jul 2

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Savannah (SAV)

Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

Top Callawassie Island hotels deals

Hilton Beachfront Resort & Spa Hilton Head Island

1 Hotel Circle Hilton Head Island SC

Free Cancellation

Reserve now, pay when you stay

$310 nightly

$341 total

May 27 - May 28

Total with taxes and fees

A full-service spa, 5 restaurants, and 2 outdoor pools are all featured at this luxury resort. Dine at the beachfront restaurant and relax with beach umbrellas. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Spa

Beach House Resort Hilton Head

1 South Forest Beach Drive Hilton Head Island SC

Free Cancellation

Reserve now, pay when you stay

$284 nightly

$312 total

May 28 - May 29

Total with taxes and fees

This hotel features 2 bars/lounges, a beach bar, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the outdoor pool, poolside bar, and concierge services.

Pool

Pet friendly

Sonesta Resort Hilton Head Island

130 Shipyard Drive Hilton Head Island SC

Free Cancellation

Reserve now, pay when you stay

$392 nightly

$431 total

May 25 - May 26

Total with taxes and fees

A full-service spa, 5 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Families will appreciate the children's club and onsite laundry facilities. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.

Pool

Hot Tub

The Westin Hilton Head Island Resort & Spa

2 Grasslawn Ave Hilton Head Island SC

Free Cancellation

Reserve now, pay when you stay

$360 nightly

$396 total

May 26 - May 27

Total with taxes and fees

This smoke-free hotel features a golf course, a full-service spa, and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area.

Pool

Hot Tub

Omni Hilton Head Oceanfront Resort

23 Ocean Lane Hilton Head Island SC

Free Cancellation

Reserve now, pay when you stay

$512 nightly

$557 total

May 31 - Jun 1

Total with taxes and fees

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's club and a children's pool, and supervised childcare is an added bonus. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.

Pool

Spa

Holiday Inn Express Hilton Head Island by IHG

10 Tanglewood Drive Hilton Head Island SC

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$164 total

May 25 - May 26

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy freebies like buffet breakfast and a beach shuttle

Pool

Breakfast included

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Rose Hill Mansion

You can find out about the history of Bluffton with a stop at Rose Hill Mansion. Amble around this family-friendly area's beautiful beaches, or seek out the golf courses.

Arch and two white chairs prepared for weeding ceremony, Poland

Rose Hill Golf Club

Enjoy a round of golf in Bluffton at Rose Hill Golf Club. Wander the beautiful beaches and seaside in this family-friendly area.

Tanger Outlets Hilton Head

4.5/5(36 reviews)

You can search for that perfect souvenir at Tanger Outlets Hilton Head during your trip to Bluffton. Wander the beautiful beaches and seaside in this family-friendly area.

Frequently asked questions

How much are vacation packages to Callawassie Island?

Travelocity has package deals to Callawassie Island, as well as flights and hotels, starting from as low as $607. With all the extra cash, you could purchase some cool tours or maybe also add a couple of extra nights to your adventure.

Where can I get the best vacation package deals for Callawassie Island?

You'll discover a terrific range of Callawassie Island package deals on Travelocity. With no less than 400 partner airlines and 1,000,000 properties across the globe, organizing the ultimate vacation will be simple.

Why should I book my Callawassie Island vacation bundle via Travelocity?

We have experiences and destinations to suit every type of traveler, exceptional service and round-the-clock customer support. And to top it off, we'll match any better price you're able to find with our Price Match Guarantee.

Will I save money on my Callawassie Island car rental if I book it with hotels and flights?

Combining your bookings into a Callawassie Island vacation package will leave you with some serious savings. Combine a car and flight; a hotel, car and flight; or a car and hotel. You won't find a better way to explore the greater Callawassie Island region than with your own ride. You can also add tours and experiences to your Travelocity package.

Where should I stay when visiting Callawassie Island?

If you're looking for someplace comfortable to base yourself, check out the Bright 3 Bdrm -2 bath Coastal Villa on Exclusive Callawassi Island-Golf Included. It's the top choice for many travelers.