Search Deals onCayman Islands Vacation Packages
Cayman Islands Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Grand Cayman Marriott Resort
Save 100% on your flight
per person
Apr 21 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
Black Urchin
Save 100% on your flight
per person
Apr 21 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this 4.5-star luxury hotel in Bodden Town. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Boddentown Art Shop and Mission House are located nearby.
VIDA Cayman
Save 100% on your flight
per person
Apr 21 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this 4-star beach hotel in West Bay. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Seven Mile Beach and Barker's National Park are located nearby.
Hotel Indigo Grand Cayman by IHG
Save 100% on your flight
per person
Apr 21 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this 4.5-star 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.
Lighthouse Point Residences
Northwest Point
Save 100% on your flight
per person
Apr 21 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this 3.5-star condo in West Bay. Enjoy free WiFi, free parking, and furnished balconies. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Club Suites at Rum Point
Save 100% on your flight
per person
Apr 21 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this 4-star 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
Save 100% on your flight
per person
Apr 21 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this 3.5-star 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.
Cayman Luxury Rentals at One Canal Point
Save 100% on your flight
per person
Apr 21 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Stay at this 4-star villa in Seven Mile Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Seven Mile Beach and Port of Georgetown 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, Po Box 30371, Seven Mile Beach, Grand Cayman
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and ...
Hotel Indigo Grand Cayman by IHG
32 Seafire Way, Seven Mile Beach, West Bay
Stay at this 4.5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Port ...
The Ritz-Carlton, Grand Cayman
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
Stay at this 5-star luxury resort in Seven Mile Beach. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our ...
Save an average of 15% on thousands of hotels when you're signed in
Hampton by Hilton Grand Cayman Seven Mile Beach
22 Piper Way, Seven Mile Beach
Stay at this 4-star resort in Seven Mile Beach. Enjoy free breakfast, free parking, and a health club. Our guests praise the breakfast and the pool in our reviews. ...
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way, Seven Mile Beach, Grand Cayman
Stay at this 5-star 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 ...
Governors Village Seven Mile Beach Corridor
1240 W Bay Rd, Seven Mile Beach, Grand Cayman
Stay at this 3.5-star business-friendly apartment in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and a garden. Popular attractions Port of ...
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Seven Mile Beach, P.O. Box 30620, Seven Mile Beach, Grand Cayman
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 6 restaurants, and a private beach. Our guests praise the helpful staff and ...
The Locale Hotel Grand Cayman
455 West Bay Road, Seven Mile Beach, Grand Cayman
Stay at this 3.5-star business-friendly hotel in Seven Mile Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast 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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Apr 5 - Mon, Apr 14
YYZ
Pearson Intl.
GCM
Owen Roberts Intl.
$332 Roundtrip, found 5 days ago
$332
Roundtrip
found 5 days ago
Wed, Apr 23 - Tue, Apr 29
JFK
John F. Kennedy Intl.
GCM
Owen Roberts Intl.
$352 Roundtrip, found 3 days ago
$352
Roundtrip
found 3 days ago
Mon, Apr 7 - Mon, Apr 14
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$352 Roundtrip, found 5 days ago
$352
Roundtrip
found 5 days ago
Thu, Apr 24 - Wed, Apr 30
JFK
John F. Kennedy Intl.
GCM
Owen Roberts Intl.
$361 Roundtrip, found 3 days ago
$361
Roundtrip
found 3 days ago
Discover Other Travel Deals
- Seven Mile Beach Vacations
- West Bay Vacations
- North Side Vacations
- East End Vacations
- Bodden Town Vacations
- George Town Vacations
- Rum Point Vacations
- Little Cayman Vacations
- Savannah Vacations
- West End Vacations
- Colliers Bay Vacations
- Tibbett's Turn Vacations
- Blossom Village Vacations
- East End Vacations
- Spot Bay Vacations