Vacation Packages to Cayman Islands for 2026
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Cayman Islands Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Shangri-La Boutique Bed & Breakfast
Mar 8 - Mar 15
7 night stay
Chicago (ORD) to George Town (GCM)
United • Roundtrip • Coach
Price was $2,622, price is now $1,916 per person
$1,916
per person
found 1 day ago
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.
4.0-star property
VIDA Cayman
Mar 7 - Mar 12
5 night stay
Washington (WAS) to George Town (GCM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $3,910, price is now $2,452 per person
$2,452
per person
found 1 day ago
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.
3.5-star property
Wyndham Reef Resort Grand Cayman
Mar 8 - Mar 15
7 night stay
Chicago (ORD) to George Town (GCM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $3,496, price is now $2,318 per person
$2,318
per person
found 1 day ago
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.
4.0-star property
Club Suites at Rum Point
Mar 8 - Mar 15
7 night stay
Chicago (ORD) to George Town (GCM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $7,413, price is now $5,441 per person
$5,441
per person
found 1 day ago
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.
4.5-star property
Hotel Indigo Grand Cayman by IHG
Mar 8 - Mar 15
7 night stay
Chicago (ORD) to George Town (GCM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $4,058, price is now $2,980 per person
$2,980
per person
found 1 day ago
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.
4.5-star property
Grand Cayman Marriott Resort
Mar 8 - Mar 15
7 night stay
Chicago (ORD) to George Town (GCM)
United • Roundtrip • Coach
Price was $3,126, price is now $2,442 per person
$2,442
per person
found 1 day ago
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 clean rooms in our reviews. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
2.0-star property
Luxury Penthouse Condo With 360 Oceanviews
Mar 6 - Mar 13
7 night stay
Chicago (ORD) to George Town (GCM)
JetBlue Airways • Non-stop • Coach
George Town (GCM) to Chicago (ORD)
Air Canada • Non-stop • Coach
Save 100% on your flight
Price was $14,379, price is now $11,756 per person
$11,756
per person
found 1 day ago
Stay at this apartment in Seven Mile Beach. Enjoy free parking and a beach locale. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
2.0-star property
Garden View Unit at Plantana Condominiums
Mar 7 - Mar 12
5 night stay
Washington (WAS) to George Town (GCM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $4,298, price is now $3,561 per person
$3,561
per person
found 1 day ago
Stay at this apartment in Seven Mile Beach. Enjoy a garden. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
4.0-star property
Sunshine Suites Resort
Mar 8 - Mar 15
7 night stay
Chicago (ORD) to George Town (GCM)
United • Roundtrip • Coach
Price was $2,646, price is now $2,205 per person
$2,205
per person
found 1 day ago
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.
5.0-star property
The Ritz-Carlton, Grand Cayman
Mar 8 - Mar 15
7 night stay
Chicago (ORD) to George Town (GCM)
United • Roundtrip • Coach
Save 100% on your flight
Price was $19,478, price is now $16,421 per person
$16,421
per person
found 1 day ago
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. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
2.0-star property
NEW Oceanfront Condo in George Town
Mar 6 - Mar 13
7 night stay
Chicago (ORD) to George Town (GCM)
JetBlue Airways • Non-stop • Coach
George Town (GCM) to Chicago (ORD)
Air Canada • Non-stop • Coach
Price was $2,496, price is now $2,128 per person
$2,128
per person
found 1 day ago
Stay at this apartment in George Town. Enjoy free parking. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
5.0-star property
The Grove
Mar 8 - Mar 15
7 night stay
Chicago (ORD) to George Town (GCM)
United • Roundtrip • Coach
Price was $3,077, price is now $2,669 per person
$2,669
per person
found 1 day ago
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 Georgetown are located nearby.
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Seven Mile Beach
Top Hotel Deals
Hotel Indigo Grand Cayman by IHG
32 Seafire Way Seven Mile Beach West Bay
13.88 km from city center
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 ...
Grand Cayman Marriott Resort
389 West Bay Road Seven Mile Beach Grand Cayman
13.54 km from city center
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 ...
The Locale Hotel Grand Cayman
455 West Bay Road Seven Mile Beach Grand Cayman
13.46 km from city center
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 Ritz-Carlton, Grand Cayman
West Bay Road Seven Mile Beach Grand Cayman
13.42 km from city center
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. ...
The Grove
1350 W Bay Rd Seven Mile Beach West Bay
13.74 km from city center
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 ...
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
14.15 km from city center
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 ...
Hampton by Hilton Grand Cayman Seven Mile Beach
22 Piper Way Seven Mile Beach
13.58 km from city center
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
13.5 km from city center
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 ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Feb 17 - Sat, Feb 28
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$325 Roundtrip, found 2 days ago
$325
Roundtrip
found 2 days ago
Wed, Feb 18 - Sat, Feb 28
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$335 Roundtrip, found 2 days ago
$335
Roundtrip
found 2 days ago
Fri, Feb 20 - Tue, Feb 24
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$385 Roundtrip, found 2 days ago
$385
Roundtrip
found 2 days ago
Thu, Feb 19 - Mon, Feb 23
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$391 Roundtrip, found 2 days ago
$391
Roundtrip
found 2 days ago