Sister Islands Vacation Packages 2026 from $1,250

Sister Islands flight + hotel vacation packages

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

Le Soleil d'Or CaymanBrac

$1,250

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to West End (CYB)

This hotel features an outdoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking. A coffee shop, free WiFi in public areas, and a garden are also on offer.

Conch Club Cottage

$1,338

per person

Dec 5 - Dec 12

found 13 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Little Cayman (LYB)

This hotel's 2 outdoor pools and hot tub are among the featured amenities. Take the free beach shuttle and relax with free beach cabanas and sun loungers. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free beach shuttle.

Top Sister Islands hotels deals

Le Soleil d'Or CaymanBrac

2147 South Side Road West End

$503 nightly

$555 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features an outdoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking. A coffee shop, free WiFi in public areas, and a garden are also on offer.

Pool

Breakfast included

Conch Club Cottage

1200 Guy Banks Road Little Cayman Cayman Islands

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This hotel's 2 outdoor pools and hot tub are among the featured amenities. Take the free beach shuttle and relax with free beach cabanas and sun loungers. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free beach shuttle.

Pool

Hot Tub

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

Stake Bay Cayman Brac

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This vacation home features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

Incredible Views, Waterfront Luxury Private Villa with Central AC

Stake Bay

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An outdoor pool is featured at this villa, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Concierge services are provided for your convenience.

Pool

Kitchen

Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

Cayman Brac Sister Islands

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This vacation home features limo/town car service, laundry facilities, and concierge services. Barbecue grills are provided for your convenience.

Kitchen

Washer

Peaceful Penthouse Getaway with Stunning Views

Cayman Brac West End

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An outdoor pool is featured at this condo, along with laundry facilities.

Pool

Kitchen

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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.

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.

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Frequently asked questions

How much are vacation packages to Sister Islands?

You might be pleasantly surprised — you can vacation in Sister Islands for only $1,250. Let Travelocity save you money and stress with our awesome vacation package deals. With hotels, flights and tours all ready to be snapped up, why wait any longer?

Where can I get the best vacation package deals for Sister Islands?

You'll discover an amazing range of Sister Islands package deals on Travelocity. With 400 partner airlines and 1,000,000 properties across the globe, piecing together the perfect vacation won't take long.

Why should I book my Sister Islands vacation bundle with Travelocity?

Savings, support and a stress-free booking are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to round-the-clock support. With the Travelocity Price Match Guarantee, you can rest easy knowing you're getting the best deal available.

Can I save on my Sister Islands car rental if I combine it with hotels and flights?

You certainly can with our Sister Islands vacation packages. With one of these, there are tons of ways to stretch your vacation budget further. Bundle any two or more car, hotel, flight and tour bookings and watch your savings pile up. With your own set of wheels, all the attractions around Sister Islands are a fun road trip away.

Which airport is best for Sister Islands?

Gerrard Smith Intl. Airport (CYB) and Edward Bodden Airfield Airport (LYB) are the two best airports for jetting to Sister Islands.

What is there to do in Sister Islands?

Sister Islands boasts hidden gems around every turn, however make sure you get to Cayman Brac Beaches and Little Cayman Beach during your stay. These landmarks are very popular with visitors to the region.