Search Deals onCayman Islands Vacation Packages
Cayman Islands Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Ocean Paradise
Save 100% on your flight
Price was $1,852, price is now $1,308 per person
$1,308
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to George Town (GCM)
Book a stay at this beach vacation home in North Side. Enjoy free WiFi, free parking, and a garden. Popular attractions Cayman Kai Public Beach and Star Fish Point are located nearby.
Hotel Indigo Grand Cayman by IHG
Price was $4,490, price is now $2,771 per person
$2,771
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
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 Georgetown are located nearby.
Shangri-La Boutique Bed & Breakfast
Price was $2,144, price is now $1,419 per person
$1,419
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
Stay at this hotel in West Bay. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Price was $5,602, price is now $3,931 per person
$3,931
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
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 property condition in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Sunshine Suites Resort
Price was $2,255, price is now $1,611 per person
$1,611
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
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 and the helpful staff in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
VIDA Cayman
Price was $2,683, price is now $1,989 per person
$1,989
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
Book a stay at this beach hotel in West Bay. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Seven Mile Beach and Barker's National Park are located nearby.
Club Suites at Rum Point
Save 100% on your flight
Price was $3,626, price is now $2,736 per person
$2,736
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
Book a stay at this beach hotel in North Side. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Rum Point Beach and Cayman Kai Public Beach are located nearby.
Wyndham Reef Resort Grand Cayman
Price was $2,375, price is now $1,832 per person
$1,832
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
Book a stay at this beach resort in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Colliers Public Beach and Barefoot Beach are located nearby.
3-4 Night Vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Cayman Islands
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
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 ...
Hotel Indigo Grand Cayman by IHG
32 Seafire Way Seven Mile Beach West Bay
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 ...
The Ritz-Carlton, Grand Cayman
West Bay Road Seven Mile Beach Grand Cayman
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. ...
Save an average of 15% on thousands of hotels when you're signed in
The Locale Hotel Grand Cayman
455 West Bay Road Seven Mile Beach Grand Cayman
Book a stay at this business-friendly hotel in Seven Mile Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Grove
1350 W Bay Rd Seven Mile Beach West Bay
Book a stay at this luxury aparthotel in Seven Mile Beach. Enjoy free WiFi, free parking, and 3 restaurants. Popular attractions Seven Mile Beach and Port of ...
Hampton by Hilton Grand Cayman Seven Mile Beach
22 Piper Way Seven Mile Beach
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. ...
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Seven Mile Beach Seven Mile Beach Grand Cayman
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 ...
Sunshine Suites Resort
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
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 ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Mar 10 - Sat, Mar 14
YYZ
Pearson Intl.
GCM
Owen Roberts Intl.
$286 Roundtrip, found 2 hours ago
$286
Roundtrip
found 2 hours ago
Fri, Mar 13 - Tue, Mar 17
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$333 Roundtrip, found 6 days ago
$333
Roundtrip
found 6 days ago
Wed, Mar 25 - Thu, Mar 26
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$405 Roundtrip, found 3 days ago
$405
Roundtrip
found 3 days ago
Fri, Jun 19 - Thu, Jun 25
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$458 Roundtrip, found 2 days ago
$458
Roundtrip
found 2 days ago
Discover Other Travel Deals
- Seven Mile Beach Vacations
- North Side Vacations
- East End Vacations
- West Bay Vacations
- George Town Vacations
- Bodden Town Vacations
- Rum Point Vacations
- Little Cayman Vacations
- West End Vacations
- Savannah Vacations
- Colliers Bay Vacations
- Tibbett's Turn Vacations
- Blossom Village Vacations
- East End Vacations
- Spot Bay Vacations