Search Deals onCayman Islands Vacation Packages
Cayman Islands Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
ONE Canal Point
Price was $1,277, price is now $932 per person
$932
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 3.5-star aparthotel in Seven Mile Beach. Enjoy free WiFi, free 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.
Galleon Villas by Hello Cayman Vacation
Save 100% on your flight
Price was $2,479, price is now $1,465 per person
$1,465
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 3.5-star beach villa in Seven Mile Beach. Enjoy free WiFi, free parking, 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.
Kimpton Seafire Resort + Spa by IHG
Save 100% on your flight
Price was $2,001, price is now $1,231 per person
$1,231
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
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 condition in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Wyndham Reef Resort Grand Cayman
Save 100% on your flight
Price was $1,581, price is now $1,049 per person
$1,049
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Silver Reef Residencies
Save 100% on your flight
Price was $2,073, price is now $1,428 per person
$1,428
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 4-star beach apartment in North Side. Enjoy free WiFi, free parking, and a private beach. Popular attractions Babylon (Dive Site) and Mastic Trail North Trailhead are located nearby.
Cayman Luxury Rentals at Sunset Cove
Save 100% on your flight
Price was $3,001, price is now $2,111 per person
$2,111
per person
Oct 25 - Nov 1
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 3.5-star beach condo in Seven Mile Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
Black Urchin
Save 100% on your flight
Price was $11,372, price is now $8,212 per person
$8,212
per person
Oct 25 - Nov 1
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Governors Village Seven Mile Beach Corridor
Price was $1,390, price is now $1,011 per person
$1,011
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
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.
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
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 ...
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
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 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
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 ...
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 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, 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 ...
Governors Village Seven Mile Beach Corridor
KY1-1206, Seven Mile Beach Corridor, 1240 W. Bay Rd., Seven Mile Beach, Grand Cayman
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Nov 1 - Sat, Nov 8
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$280 Roundtrip, found 10 hours ago
$280
Roundtrip
found 10 hours ago
Sun, Sep 21 - Mon, Sep 29
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$360 Roundtrip, found 2 days ago
$360
Roundtrip
found 2 days ago
Sat, Apr 18 - Tue, Apr 21
LGA
LaGuardia
GCM
Owen Roberts Intl.
$387 Roundtrip, found 6 days ago
$387
Roundtrip
found 6 days ago
Sun, Oct 19 - Sun, Oct 26
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$391 Roundtrip, found 1 day ago
$391
Roundtrip
found 1 day ago
Discover Other Travel Deals
- Seven Mile Beach Vacations
- North Side Vacations
- East End Vacations
- George Town Vacations
- West Bay Vacations
- Bodden Town Vacations
- Rum Point Vacations
- Little Cayman Vacations
- West End Vacations
- Savannah Vacations
- Colliers Bay Vacations
- Blossom Village Vacations
- Tibbett's Turn Vacations
- East End Vacations
- Spot Bay Vacations
