Sister Islands Vacation Packages

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Photo by Bob Bowdey

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    Save up to CA $4,200 when you book a flight and hotel together*

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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 $2,454, price is now CA $1,992 per person
CA $1,992
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Little Cayman (LYB)
10/10 Exceptional! (7 reviews)
Adorable tiny cottage with modern amenities, direct access to pool and beach. Place was clean equipped with everything needed for a short stay. The beds were not very comfortable but we still enjoyed our stay very much and would stay again any day of the week!

Reviewed on Nov 4, 2025

Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was CA $2,980, price is now CA $2,416 per person
CA $2,416
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to West End (CYB)
9.4/10 Exceptional! (16 reviews)
The room and amenities were spotless. The food was excellent as well as the service. Beautiful and quiet

Reviewed on Feb 16, 2026

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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
The price is CA $554 per night from Jun 18 to Jun 19
CA $554
CA $763 total
Jun 18 - Jun 19
includes taxes & fees
9.4/10 Exceptional! (16 reviews)
"Awesome 👍"

Reviewed on Feb 24, 2026

Le Soleil d'Or CaymanBrac
RazorBrac SeaEsta - Private Beachfront Home

RazorBrac SeaEsta - Private Beachfront Home

Cayman Brac Sister Islands
10/10 Exceptional! (33 reviews)
"Lovely and wonderful house provided relaxing getaway for a couple. Caretaker met us at airport and lead us to house was very helpful as we landed after sunset and house is off a side road. Well stocked kitchen. Comfortable bed. Plenty of linens. Very clean. Washer dryer is a plus. Excellent WiFi. ..."

Reviewed on Apr 30, 2026

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RazorBrac SeaEsta - Private Beachfront Home
Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck

Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck

Cayman Brac
10/10 Exceptional! (65 reviews)
"Best getaway of my life. The snorkeling out front (and half a mile up the road) was amazing! Beautiful space, great neighbors. Amazing A/C and comfy beds."

Reviewed on Apr 24, 2026

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Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck
See all 79 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
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Stay near popular Sister Islands attractions

Little Cayman Beach

3.7/5 (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

Can I cancel my flight booking to Sister Islands due to COVID-19?
If you've yet to book your tickets, read the terms and conditions of your preferred carrier. If you've already secured your flight to Sister Islands, click through to our Customer Service Portal. It will help determine which COVID-19 policies are applicable to your reservation and offer advice on the next steps.
What's the best way to find cheap flights to Sister Islands that have flexible change policies?
By using our clever "No change fee" filter, that's how. Simply type in your travel dates, click the "Search" button, then select the box directly below the "Flexible change policies" subheading (look to the left of your screen). Expedia makes it easy to find affordable, flexible fares to Sister Islands.
What are some of the general tips for travelers to Sister Islands during the COVID-19 outbreak?
If it's your first time traveling during the COVID-19 pandemic, you'll notice a range of new standards and rules in place. Follow these tips and make your trip to Sister Islands go off without a hitch:
  • Research if any travel restrictions apply to your origin and destination before locking in a flight. Also check if there are any special conditions you'll have to follow on arrival, such as taking a COVID-19 test.
  • Keep your face mask on during airport screening. A TSA employee will require you to lower your mask temporarily for ID purposes.
  • You're no longer required to hand your boarding pass (paper or electronic) directly to a TSA officer. Instead, you should position the pass on the reader and then hold it up for the agent to visually inspect it.
  • You're allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. This will need to be removed for X-ray screening.
  • Put any personal items (phone, wallet and keys for example) in your carry-on rather than a bin to reduce handling during screening.
  • Transport all food items in a clear plastic bag and also put them in a screening bin. Keeping food separate from your carry-on means it's less likely a TSA agent will need to touch and open your bag for inspection.

Which airlines fly to Sister Islands?
Reserve your ticket with Cayman Airways and start working on your Sister Islands must-do list. This top airline runs 390 flights per month to Owen Roberts Intl. Airport (GCM), a main gateway.
How can I find cheap tickets to Sister Islands?
Book well ahead of time, consider nearby airports, avoid peak travel periods — there are plenty of ways! Another one is to use Expedia's "flexible dates" function. Find a Sister Islands flight, then compare the prices for nearby dates. In the last seven days, the best price for a flight to Sister Islands was .
How much is a flight to Sister Islands?
In the last seven days, round-trip flights to Sister Islands sold for as low as and reached a maximum price of . For one-way trips leaving (), the lowest price during this time was .
What are the most popular airports to fly into in Sister Islands?
Prepare to pack your bags and fly into Owen Roberts Intl. Airport (GCM), Sister Islands's primary flight hub. Lock in a seat on one of the 408 flights that touch down at this well-known destination each month.
When is the cheapest time to fly to Sister Islands?
Consider jetting off early in the week to secure a bargain airfare to Sister Islands. Tuesday is routinely the most economical day to take off, with Monday running a close second. Saturday often has the costliest prices. This is because a lot of travelers prefer to start their getaway on a weekend.
How much is a plane ticket to Sister Islands?
Ticket prices ranged from to over the last seven days. When you're ready to book, we're ready to help you find a cheap flight to Sister Islands.
Which airlines with flights to Sister Islands employ COVID-19 cleanliness policies?
With the various changes to travel due to the COVID-19 outbreak, most reputable airlines have adopted social distancing protocols and other hygiene measures. We've listed some of these carriers below:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.