Sister Islands Vacation Packages 2025/2026 from $1,344

Sister Islands flight + hotel vacation packages

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

Conch Club Cottage

$1,344

per person

Oct 10 - Oct 15

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Little Cayman (LYB)

A private beach, 2 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining 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

$1,834

per person

Nov 8 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to West End (CYB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a garden, and luggage storage are also on offer.

Top Sister Islands hotels deals

Serenity On The Bay2 - Two Bed Apt Close to Supermarkets, Shops and Restaurants!

Get rates

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

Hot Tub

Air conditioning

Beach Front Paradise Home. Luxurious Funishings!

Get rates

An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Pool

Kitchen

Le Soleil d'Or CaymanBrac

2147 South Side Road, West End

$446 nightly

$492 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a garden, and luggage storage are also on offer.

Pool

Breakfast included

Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!

Get rates

This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

Get rates

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

Get rates

A private beach, 2 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with free beach cabanas and sun loungers. Families will appreciate the onsite laundry facilities and in-room childcare.

On private beach

Pool

Don't see what you're looking for?

See all available properties in Sister Islands

View all properties

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

Little Cayman Beach

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.

South Hold Sound

Commune with nature and explore the great outdoors at South Hold Sound during your travels in Blossom Village. Amble around the area's beaches or experience its museums.

Booby Pond Nature Reserve

Explore the great outdoors at Booby Pond Nature Reserve, a lovely green space in Blossom Village. Stroll along the beaches or experience the area's museums.

Frequently asked questions

How much are vacation packages to Sister Islands?

You might be pleasantly surprised — you can vacation in Sister Islands for only $1,344. 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.