Sister Islands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Bob Bowdey

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Sister Islands Vacation Deals

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

Conch Club Cottage

2 out of 5
Price was CA $3,077, price is now CA $2,147 per person
CA $2,147
per person
Jan 6 - Jan 13
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was CA $3,120, price is now CA $2,389 per person
CA $2,389
per person
Jan 6 - Jan 13
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to West End (CYB)
9.2/10 Wonderful! (20 reviews)

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Sister Islands Hotel Deals

Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
2147 South Side Road West End
Fully refundableReserve now, pay when you stay
The price is CA $536 per night from Dec 1 to Dec 2
CA $536
CA $748 total
Dec 1 - Dec 2
includes taxes & fees
Le Soleil d'Or CaymanBrac
Conch Club Cottage

Conch Club Cottage

2 out of 5
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

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

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

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Luxury Oceanfront Cayman Brac Escape, Private Pool, 3BR Stunning Caribbean Views
See all 78 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

Frequently asked questions

How much does a Sister Islands vacation package cost?
Discover the best of Sister Islands from just CA $2,147. Choose from a great selection of flights, rental cars and hotels to suit every style and budget. Score even more discounts when you add a few sightseeing activities to your package.
How do I get a cheap travel package to Sister Islands?
Bundling your hotel and flight with Expedia won't just save valuable time — it'll save you a few dollars too. A Sister Islands vacation package makes it simple to create the perfect trip. With more than 550 airlines worldwide to choose from, finding flights that fit your schedule won't be an issue. On top of that, we have over 1,000,000 hotels globally to pick from. Now that's what we call choice. Whatever your budget, Expedia can show you the world.
What are the top hotels in Sister Islands?
Grand Cayman Marriott Resort and The Locale Hotel Grand Cayman know how to make their guests feel welcome in West End. If you also plan to stay in Little Cayman, look up The Westin Grand Cayman Seven Mile Beach Resort & Spa and Sunshine Suites Resort. Both are very popular with travelers.
How far in advance should I book my Sister Islands vacation?
Search Expedia to compare international airfares as soon as you know your travel dates. You can normally purchase a seat up to 12 months before departure. If you can't find your preferred air carrier, or you're booking late, fear not. The lowest prices to Sister Islands sometimes emerge a few weeks before departure.
What does an Expedia Sister Islands travel package include?
Car rentals, hotels and flights — we bring you the very best deals. All you'll have to do is pick and choose your favorite combination. After you've made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it simple to customize an amazing Sister Islands trip.
What should I know before booking a Sister Islands travel package?
You'll enjoy excellent savings when you bundle your flights, hotels and rental cars into a travel package. Plus, booking everything in one place simply makes planning easier. So why waste your time or money? Whether you're putting together a fancy romantic getaway or a low-cost family road trip, have a look at our vacation packages today.
Can I choose my airline with a Sister Islands Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the freedom to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Sister Islands vacation package?
We totally get that unexpected stuff happens. If you've booked a Sister Islands vacation package and have to cancel or change it, we're here to help. It's always worth taking a look at our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may charge a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.