Sister Islands Vacation Packages 2026 from $974

Sister Islands flight + hotel vacation packages

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

Conch Club Cottage

$974

per person

Sep 15 - Sep 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Little Cayman (LYB)

This hotel features 2 outdoor pools, a hot tub, and 2 beach bars. Take the free beach shuttle and relax with free beach cabanas and sun loungers. Families will appreciate the onsite laundry facilities and in-room childcare.

Le Soleil d'Or CaymanBrac

$1,871

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip non-stop flight included

Des Moines (DSM) 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.

Top Sister Islands hotels deals

Le Soleil d'Or CaymanBrac

2147 South Side Road West End

Free Cancellation

Reserve now, pay when you stay

$499 nightly

$551 total

Jul 21 - Jul 22

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

RazorBrac SeaEsta - Private Beachfront Home

Cayman Brac Sister Islands

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This vacation home features laundry facilities.

Kitchen

Washer

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.

Pool

Hot Tub

Conch Club Cottage

1200 Guy Banks Road Little Cayman Cayman Islands

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This hotel features 2 outdoor pools, a hot tub, and 2 beach bars. Take the free beach shuttle and relax with free beach cabanas and sun loungers. Families will appreciate the onsite laundry facilities and in-room childcare.

Pool

Hot Tub

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

Serenity On The Bay2 - Two Bed Cayman Brac - Airport Shops Restaurants Close!

Cayman Brac Cayman Islands

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A hot tub is featured at this guesthouse, along with laundry facilities and barbecue grills.

Hot Tub

Free WiFi

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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 $974. 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.