Cayman Islands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Cayman Islands Department of Tourism
    deals illustration
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Your Cayman Islands Vacation

Book a vacation package to Cayman Islands and go wherever your adventurous soul leads you. This exciting destination has so much to offer, including its underwater activities, distilleries and craft breweries, coastal beaches, and so much more. Kick off your trip to Cayman Islands with some time exploring East End visiting popular sights like Grand Cayman Blow Holes and Barefoot Beach. West Bay is another city that lures crowds from far and wide. Seven Mile Beach and Stingray City are two of the top places to see in this destination. When it's time to stop dreaming and start travelling, Expedia will help turn your Cayman Islands vacation into reality.

Top vacation destinations in Cayman Islands

FlightsFlightsHotelsHotels

Seven Mile Beach

Seven Mile Beach

Top Cayman Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

3.5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 20
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to George Town (GCM)
10/10 Exceptional! (192 reviews)
We’ve been to grand cayman six times over the past 30 years. The Villas at the Galleon oceanfront condo was easily the best place we’ve stayed. It’s modern, clean and well-appointed. The host was helpful and prompt. The location can’t be beat. It’s right on a gorgeous section of seven mile beach between the Ritz-Carlton and the Westin. It was perfect for a family of five.

Reviewed on Jun. 23, 2025

Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Aug 25 - Sep 1
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
10/10 Exceptional! (2 reviews)
Property is Beautiful and very private. One downside is being so far from extracurricular activities

Reviewed on Mar. 26, 2025

Cayman Luxury Rentals at Sunset Cove

Cayman Luxury Rentals at Sunset Cove

3.5 out of 5
Save 100% on your flight
per person
Aug 25 - Sep 1
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
No reviews
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Save 100% on your flight
per person
Aug 25 - Sep 1
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
9.6/10 Exceptional! (24 reviews)
Amazing, beautiful property! Fantastic food, gorgeous pool! Can't wait to go back.

Reviewed on Jul. 2, 2025

VIDA Cayman

VIDA Cayman

4 out of 5
Save 100% on your flight
per person
Aug 25 - Sep 1
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
9.8/10 Exceptional! (7 reviews)
The food is tremendous. The chefs are excellent. Everything is fresh and delicious. The staff was incredible the entire stay. Room was modern and everything worked perfectly. We loved everything. I do wish they had dinner service and a bartender all day, but minor inconvenience.

Reviewed on Jun. 20, 2025

Cayman Islands Vacation

A Caribbean paradise, the Cayman Islands will captivate you from the moment you set foot on the territory’s pristine shores.

Cayman Islands Hotel + Flight

Looking for an easy way to save some money on your getaway? Build your own Cayman Islands Vacation Package with Expedia. With hotels starting at CA $221 a night, and an impressive 1,513 options to choose from, you'll get more bang for your Cayman Islands dollar than if you booked separately. We have everything you need for a fantastic Cayman Islands getaway — flights, hotels, car rental, tours and experiences.

Your Cayman Islands Vacation Itinerary

  • Day 1: Fly into Owen Roberts International Airport in Grand Cayman and start your adventure. For an unforgettable experience, head to Stingray City, where you can pet and feed gentle stingrays. Don’t miss the spectacular Cayman Crystal Caves either, where stalactite and stalagmite crystal structures await.

  • Day 2: A full-day tour of Grand Cayman Island is the perfect way to learn more about its many treasures, including Seven Mile Beach and the Cayman Turtle Farm. As the sun begins to set, cast away on a romantic sunset cruise with a rum cocktail in hand. Spend the rest of the evening discovering the vibrant nightlife of the capital George Town.

  • Day 3-4: Take a quick flight to Little Cayman Island and you’ll find yourself in a remote paradise. Explore wonders like South Hole Sound Lagoon, visit Booby Pond Nature Reserve and dive at Bloody Bay Wall Marine Park.

Cayman Islands Information

  • Don’t miss Pirate Week, more than a week’s worth of swashbuckling fun and festivities held each November. The festival kicks off with an invasion by sea as two pirate ships converge on George Town Harbour to take the local governor captive.

  • Getaways should be about rest and relaxation. Why not check in to aCayman Islands All Inclusive Resortand really put your feet up this vacation?

Cayman Islands Hotel Deals

Hotel Indigo Grand Cayman by IHG
Hotel Indigo Grand Cayman by IHG
4.5 out of 5
32 Seafire Way, Seven Mile Beach, West Bay
Fully refundable
The price is CA $378 per night from Jul 22 to Jul 23
CA $378
CA $561 total
Jul 22 - Jul 23
includes taxes & fees
9.6/10 Exceptional! (286 reviews)
"Excelente atención todo Super limpio. Maravilloso hotel"

Reviewed on Jul. 2, 2025

Hotel Indigo Grand Cayman by IHG
The Ritz-Carlton, Grand Cayman
The Ritz-Carlton, Grand Cayman
5 out of 5
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
The price is CA $924 per night from Jul 28 to Jul 29
CA $924
CA $1,272 total
Jul 28 - Jul 29
includes taxes & fees
9.4/10 Exceptional! (998 reviews)
"Everyone was very nice and treated us like royalty"

Reviewed on Jun. 28, 2025

The Ritz-Carlton, Grand Cayman
Hampton by Hilton Grand Cayman Seven Mile Beach
Hampton by Hilton Grand Cayman Seven Mile Beach
4 out of 5
22 Piper Way, Seven Mile Beach
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Aug 5 to Aug 6
CA $221
CA $337 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (559 reviews)
"The Hampton in Grand Cayman was wonderful. All staff was amazing, friendly and helpful. Elenora at the front desk went above and beyond, helping our group at every turn. She made us feel like we were at a luxury hotel with her attention to details."

Reviewed on Jun. 30, 2025

Hampton by Hilton Grand Cayman Seven Mile Beach
See all 1,513 properties in Cayman 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

Frequently asked questions

How much does a Cayman Islands vacation package cost?
The most affordable Cayman Islands vacation package is CA $2,349, so your dream vacation can become a reality --- without the high price tag. Bundle flights, hotels and car rentals to build a package that suits your travel style.
How do I get a cheap travel package to Cayman Islands?
Combine your hotels and flights, toss in extras such as activities, and save with a Cayman Islands vacation package. You won't just score amazing discounts on your escape --- you'll have plenty of choice at your fingertips too. When you book through Expedia, you'll have your pick of over 550 airlines and 1,000,000 hotels around the world. Your next affordable adventure starts right here, right now!
Where should I stay in Cayman Islands?
Boatswains Beach is one of the things that lures wanderers to Cayman Islands, so it should come as no surprise that many book their hotel in West Bay.
What are the top hotels in Cayman Islands?
Grand Cayman Marriott Resort and The Locale Hotel Grand Cayman know how to make their guests feel at home in Seven Mile Beach. If your travel plans also include North Side, look up The Westin Grand Cayman Seven Mile Beach Resort & Spa and Sunshine Suites Resort. Both are top picks with travelers.
How far in advance should I book my Cayman Islands vacation?
It's hard to pick the ideal time for airfares, but we generally suggest the earlier, the better. Most international flights on Expedia become available to compare up to 12 months in advance. If you can't book early, don't fret. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Cayman Islands travel package include?
Packages include rental cars, flights and hotels, but you can mix and match them to create your perfect Cayman Islands getaway. You can also add on a few tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Cayman Islands travel package?
Locking in all the parts of your trip together is a great way to save. Bundle your car rentals, airfares and hotels into a neat package. But your options don't end at hotels. Expedia has all types of properties, including vacation rentals like oceanfront condos and spacious residences. You've got choices galore!
Can I choose my airline with a Cayman Islands Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you certainly can. Simply choose your favorite carrier and craft the perfect Cayman Islands escape.
If I'm not able to travel, can I cancel my Cayman Islands vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may impose a fee if your booking is older than that.

Discover the most popular places to visit in Cayman Islands

Seven Mile Beach

Seven Mile Beach

Why not spend a lazy afternoon at Seven Mile Beach during your trip to Seven Mile Beach? Stroll along the area's seaside, or simply savor its seafood restaurants.

Seven Mile Beach

Camana Bay

4.5/5(41 reviews)

You can browse for the perfect souvenirs at Camana Bay during your visit to Seven Mile Beach. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Camana Bay

Tiki Beach

5/5(2 reviews)

If a restful vacation is part of your travel plans, Tiki Beach might be the perfect place to seek out during your trip to Seven Mile Beach. Amble around the area's seaside or seek out the snorkeling spots.

Tiki Beach

Other vacations you might like

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