Sister Islands Vacation Packages 2026 from $1,146

Photo by Bob Bowdey

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Sister Islands vacation packages

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

Conch Club Cottage

$1,146

per person

Nov 19 - Nov 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Little Cayman (LYB)

10/10 Exceptional! (7 reviews)

Very nice, recently remodeled, bright and clean.

Reviewed on Apr 7, 2026

Le Soleil d'Or CaymanBrac

$1,165

per person

Dec 10 - Dec 14

found 4 hours ago

Roundtrip non-stop flight included

Boston (BOS) to West End (CYB)

9.2/10 Wonderful! (20 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Sister Islands

View all trips

Stay near popular Sister Islands attractions

Little Cayman Beach

7.4/10 (3 reviews)

Why not spend a carefree afternoon at Little Cayman Beach during your travels in Blossom Village? While you're in the area, wander around the parks.

See properties

Cayman Brac Bluff

9.0/10 (7 reviews)

Commune with nature and explore the great outdoors at Cayman Brac Bluff during your travels in East End. Stroll along the beaches or visit the monuments while you're in the area.

See properties

Cayman Brac Beaches

7.4/10 (6 reviews)

Why not spend a lazy afternoon at Cayman Brac Beaches during your trip to West End? Wander the parks and seaside while you're in the area.

See properties

Cayman Brac Lighthouse

8.8/10 (3 reviews)

You can learn about the history of East End with a visit to Cayman Brac Lighthouse. Amble around this relaxing area's beaches, or seek out the snorkeling spots.

See properties

Central Caribbean Marine Institute

Explore the campus of Central Caribbean Marine Institute during your stay in Little Cayman. While you're in the area, wander around the natural setting.

See properties

Owen Island Beach

8.0/10 (5 reviews)

Why not spend a carefree afternoon at Owen Island Beach during your travels in Blossom Village? Amble around the area's parks or experience its museums.

See properties

Westerly Ponds

7.0/10 (2 reviews)

Explore the great outdoors at Westerly Ponds, a lovely green space in West End. Wander the seaside and beaches while you're in the area.

See properties

Sister Islands Hotel Deals

Le Soleil d'Or CaymanBrac

2147 South Side Road West End

Fully refundableReserve now, pay when you stay

$462 nightly

$515 total

Oct 4 - Oct 5

Total with taxes and fees

Conch Club Cottage

1200 Guy Banks Road Little Cayman Cayman Islands

10/10 Exceptional! (7 reviews)

"Very nice, recently remodeled, bright and clean."

Reviewed on Apr 7, 2026

Get rates

Luxury Oceanfront Cayman Brac Escape, Private Pool, 3BR Stunning Caribbean Views

Stake Bay Cayman Brac

10/10 Exceptional! (72 reviews)

"Tide's End is a very nice house in a beautiful setting. We had a wonderful family vacation here. My daughter and I spent a few days scuba diving with "Reef Divers" while the rest of the family was perfectly content relaxing at the house (usually in the pool) enjoying the fantastic Caribbean views. ..."

Reviewed on Jul 21, 2026

Get rates

See all 82 properties in Sister Islands

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.