Vacation Packages to Cayman Islands for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Cayman Islands Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Governors Village Seven Mile Beach Corridor
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $1,473, price is now $1,176 per person
$1,176
per person
found 1 day ago
Stay at this 3.5-star family-friendly apartment in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and a garden. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
4.5-star property
Black Urchin
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $13,324, price is now $8,877 per person
$8,877
per person
found 1 day ago
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.
4.5-star property
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $3,528, price is now $2,578 per person
$2,578
per person
found 1 day ago
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 property condition in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
3.5-star property
Lighthouse Point Residences
Northwest Point
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Save 100% on your flight
Price was $4,745, price is now $3,490 per person
$3,490
per person
found 1 day ago
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.
4.5-star property
Hotel Indigo Grand Cayman by IHG
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $2,119, price is now $1,621 per person
$1,621
per person
found 1 day ago
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.
3.5-star property
Wyndham Reef Resort Grand Cayman
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $1,842, price is now $1,416 per person
$1,416
per person
found 1 day ago
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.
4.0-star property
On The Bay
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $2,177, price is now $1,721 per person
$1,721
per person
found 1 day ago
Stay at this 4-star beach condo in North Side. Enjoy free WiFi, free parking, and private pools. Popular attractions Cayman Crystal Caves and Babylon (Dive Site) are located nearby.
4.0-star property
VIDA Cayman
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $2,730, price is now $2,166 per person
$2,166
per person
found 1 day ago
Stay at this 4-star 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.
4.0-star property
Cayman Luxury Rentals at One Canal Point
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $2,840, price is now $2,308 per person
$2,308
per person
found 1 day ago
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.
3.5-star property
Cayman Luxury Rentals at The Grove
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $1,886, price is now $1,587 per person
$1,587
per person
found 1 day ago
Stay at this 3.5-star apartment in Seven Mile Beach. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
5.0-star property
The Ritz-Carlton, Grand Cayman
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $4,100, price is now $3,528 per person
$3,528
per person
found 1 day ago
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 reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
2.0-star property
3 Suites BP Steps to Beach
Nov 24 - Nov 29
5 night stay
New York (JFK) to George Town (GCM)
JetBlue Airways • Coach
George Town (GCM) to New York (JFK)
American Airlines • Coach
Price was $3,767, price is now $3,276 per person
$3,276
per person
found 1 day ago
Book a stay at this beach apartment in West Bay. Enjoy free parking, a full-service spa, and a beach locale. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
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The Ritz-Carlton, Grand Cayman
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
13.42 km from city center
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 ...
Hotel Indigo Grand Cayman by IHG
32 Seafire Way, Seven Mile Beach, West Bay
14.15 km from city center
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 ...
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way, Seven Mile Beach, Grand Cayman
14.13 km from city center
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 ...
Hampton by Hilton Grand Cayman Seven Mile Beach
22 Piper Way, Seven Mile Beach
13.58 km from city center
Stay at this 4-star 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. ...
Grand Cayman Marriott Resort
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
13.54 km from city center
Stay at this 4.5-star 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
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 ...
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Seven Mile Beach, P.O. Box 30620, Seven Mile Beach, Grand Cayman
13.5 km from city center
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 ...
Governors Village Seven Mile Beach Corridor
KY1-1206, Seven Mile Beach Corridor, 1240 W. Bay Rd., Seven Mile Beach, Grand Cayman
13.44 km from city center
Stay at this 3.5-star family-friendly apartment in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and a garden. Popular attractions Seven Mile ...
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.
Thu, Jan 22 - Sat, Jan 31
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Mon, Jan 26 - Thu, Feb 5
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$340 Roundtrip, found 1 day ago
$340
Roundtrip
found 1 day ago
Thu, Jan 22 - Sat, Jan 31
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$361 Roundtrip, found 2 days ago
$361
Roundtrip
found 2 days ago
Mon, Dec 1 - Tue, Dec 9
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$370 Roundtrip, found 4 days ago
$370
Roundtrip
found 4 days ago
Fri, Jan 30 - Sat, Jan 31
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$376 Roundtrip, found 2 days ago
$376
Roundtrip
found 2 days ago