$94 Cheap flights to Cayman Islands
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Top places to visit in Cayman Islands
Cheap flights to Cayman Islands from $94 One Way, $287 Round Trip
$287 return flights and $94 one-way flights to Cayman Islands were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
MIA
Miami
GCM
Grand Cayman
$287 Roundtrip, found 3 hours ago
$287
Roundtrip
found 3 hours ago
BOS
Boston
GCM
Grand Cayman
$293 Roundtrip, found 3 days ago
$293
Roundtrip
found 3 days ago
JFK
New York
GCM
Grand Cayman
$299 Roundtrip, found 12 hours ago
$299
Roundtrip
found 12 hours ago
EWR
New York
GCM
Grand Cayman
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
LGA
New York
GCM
Grand Cayman
$313 Roundtrip, found 11 hours ago
$313
Roundtrip
found 11 hours ago
TPA
Tampa
GCM
Grand Cayman
$341 Roundtrip, found 3 days ago
$341
Roundtrip
found 3 days ago
MIA
Miami
CYB
Cayman Brac
$350 Roundtrip, found 14 hours ago
$350
Roundtrip
found 14 hours ago
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| BOS | George Town | April 26 to May 2 | $322 |
| LGA | George Town | April 24 to April 27 | $329 |
| YYZ | George Town | April 26 to May 2 | $454 |
| ORD | George Town | April 24 to April 30 | $793 |
Find The Perfect Hotel For After Your Flight
Score Epic Cayman Islands Accommodation Deals
The Sunshine Hotel and Suites
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
$352 nightly
The price is $393 total per night from May 3 to May 4
$393 total
May 3 - May 4
Total with taxes and fees
Book a stay at this beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
9/10 Wonderful! (1,004 reviews)
Beautiful clean rooms. Comfy bed. Immaculate bathrooms. Friendly and helpful staff.
Reviewed on Apr 17, 2026
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
$1,046 nightly
The price is $1,169 total per night from May 9 to May 10
$1,169 total
May 9 - May 10
Total with taxes and fees
Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
9.8/10 Exceptional! (1,000 reviews)
Staff friendly. Hotel clean. Only draw back is beach staff for water sports and rental. Very rude and arrogant. Not the type that make you want to do any booking or activity with them
Reviewed on Mar 25, 2026
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Seven Mile Beach Seven Mile Beach Grand Cayman
$851 nightly
The price is $952 total per night from May 10 to May 11
$952 total
May 10 - May 11
Total with taxes and fees
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,003 reviews)
Do not stay here, tired and over priced. Much better options on Island.
Reviewed on Apr 17, 2026
Save an average of 15% on thousands of hotels when you're signed in
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$483 nightly
The price is $539 total per night from May 8 to May 9
$539 total
May 8 - May 9
Total with taxes and fees
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the ...
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.
Our Top Cayman Islands Apartment Hotels
The Sunshine Hotel and Suites
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
$352 nightly
The price is $393 total per night from May 3 to May 4
$393 total
May 3 - May 4
Total with taxes and fees
Book a stay at this beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
9/10 Wonderful! (1,004 reviews)
Beautiful clean rooms. Comfy bed. Immaculate bathrooms. Friendly and helpful staff.
Reviewed on Apr 17, 2026
Holiday Inn Resort Grand Cayman by IHG
278 Crighton Drive West Bay Grand Cayman
Fully refundable
$275 nightly
The price is $304 total per night from May 4 to May 5
$304 total
May 4 - May 5
Total with taxes and fees
Book a stay at this beach hotel in West Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.2/10 Very Good! (669 reviews)
The water from sink in bathroom has a bad smell. Toilet bowl has also some type of bad smell. But room is clean and organized. Breakfast foods great staffs are friendly. Wish the beach is not rocky
Reviewed on Apr 10, 2026
The Reef Beach Resort, East End, Grand Cayman
2221 Queens Highway East End Grand Cayman
Book a stay at this beach aparthotel in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,053 reviews)
Mixed experience at this older but clean resort. Our room was on the smaller side but had an unobstructed ocean view. Service was generally excellent and staff were friendly and responsive. One drawback was housekeeping — our room was only serviced on day four of a four-night stay, though we were ...
Reviewed on Apr 18, 2026
Save an average of 15% on thousands of hotels when you're signed in
Seven Mile Beach Resort & Club
19 D Piper Way, West Bay Road Seven Mile Beach Grand Cayman
$316 nightly
The price is $356 total per night from May 1 to May 2
$356 total
May 1 - May 2
Total with taxes and fees
Book a stay at this beach hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (424 reviews)
Property is well kept and staff are friendly. Close by to excellent restaurants and shopping.
Reviewed on Apr 18, 2026
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.
Score Epic Cayman Islands Accommodation Deals
Hotel Indigo Grand Cayman by IHG
32 Seafire Way Seven Mile Beach West Bay
$432 nightly
The price is $483 total per night from May 11 to May 12
$483 total
May 11 - May 12
Total with taxes and fees
Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Port of ...
9.8/10 Exceptional! (599 reviews)
Great restaurants!
Reviewed on Apr 20, 2026
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$483 nightly
The price is $539 total per night from May 8 to May 9
$539 total
May 8 - May 9
Total with taxes and fees
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the ...
Hampton by Hilton Grand Cayman Seven Mile Beach
22 Piper Way Seven Mile Beach
Fully refundableReserve now, pay when you stay
$300 nightly
The price is $336 total per night from May 3 to May 4
$336 total
May 3 - May 4
Total with taxes and fees
Stay at this resort in Seven Mile Beach. Enjoy free breakfast, free parking, and a beach locale. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (771 reviews)
Clean room, nice and helpful stuff.
Reviewed on Apr 19, 2026
Save an average of 15% on thousands of hotels when you're signed in
The Ritz-Carlton, Grand Cayman
West Bay Road Seven Mile Beach Grand Cayman
$1,251 nightly
The price is $1,400 total per night from May 7 to May 8
$1,400 total
May 7 - May 8
Total with taxes and fees
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (1,002 reviews)
This property is absolutely perfect, all around incredible and worth every penny
Reviewed on Apr 17, 2026
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.
Family Friendly Hotels in Cayman Islands
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
$483 nightly
The price is $539 total per night from May 8 to May 9
$539 total
May 8 - May 9
Total with taxes and fees
Book a stay at this luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the ...
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
$1,046 nightly
The price is $1,169 total per night from May 9 to May 10
$1,169 total
May 9 - May 10
Total with taxes and fees
Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
9.8/10 Exceptional! (1,000 reviews)
Staff friendly. Hotel clean. Only draw back is beach staff for water sports and rental. Very rude and arrogant. Not the type that make you want to do any booking or activity with them
Reviewed on Mar 25, 2026
Aqua Bay Club Condos
W Bay Rd Seven Mile Beach Grand Cayman
Book a stay at this beach aparthotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Seven Mile Beach and Port of ...
9.8/10 Exceptional! (91 reviews)
Aqua Bay Club exceeded our expectations! The check in was not as smooth as we would have liked, because we were arriving on a Saturday (there is no staff on site on weekends) and we had not received an email with check-in instructions so that we could get into our condo. But Expedia helped us get ...
Reviewed on Apr 21, 2026
Save an average of 15% on thousands of hotels when you're signed in
The Reef Beach Resort, East End, Grand Cayman
2221 Queens Highway East End Grand Cayman
Book a stay at this beach aparthotel in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,053 reviews)
Mixed experience at this older but clean resort. Our room was on the smaller side but had an unobstructed ocean view. Service was generally excellent and staff were friendly and responsive. One drawback was housekeeping — our room was only serviced on day four of a four-night stay, though we were ...
Reviewed on Apr 18, 2026
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.
Need a Car For After Your Flight?
Economy
Chevrolet Spark or similar
Compact
Ford Focus or similar
Midsize
Toyota Corolla or similar
SUV
Jeep Compass or similar
Cayman Islands
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.
