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Cayman Islands Vacation Packages

Cayman Islands Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

3.5 out of 5
Save 100% on your flight
Price was $1,809, price is now $934 per person
$934
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Book a stay at this beach aparthotel 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.
The Grove and The Grove Too

The Grove and The Grove Too

5 out of 5
Save 100% on your flight
Price was $2,293, price is now $1,347 per person
$1,347
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
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 Governor's Beach are located nearby.
ONE GT Grand Cayman

ONE GT Grand Cayman

4.5 out of 5
Save 100% on your flight
Price was $2,178, price is now $1,607 per person
$1,607
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Book a stay at this luxury hotel in George Town. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Port of Georgetown and Camana Bay are located nearby.
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Save 100% on your flight
Price was $4,659, price is now $3,561 per person
$3,561
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Stay at this hotel in North Side. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Grand Cayman Beaches and Rum Point Beach are located nearby.
Shangri-La Boutique Bed & Breakfast

Shangri-La Boutique Bed & Breakfast

4 out of 5
Price was $1,390, price is now $1,069 per person
$1,069
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Governor's Beach are located nearby.
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
Price was $11,990, price is now $9,276 per person
$9,276
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Book a stay at this luxury hotel in Bodden Town. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Grand Cayman Beaches and Boddentown Art Shop are located nearby.
Cayman Luxury Rentals at Ocean Paradise

Cayman Luxury Rentals at Ocean Paradise

4 out of 5
Price was $1,786, price is now $1,386 per person
$1,386
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Grand Cayman Beaches and Cayman Kai Public Beach are located nearby.
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

2.5 out of 5
Price was $1,853, price is now $1,444 per person
$1,444
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Book a stay at this family-friendly hotel in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and 2 meeting rooms. Popular attractions Governor's Beach and Seven Mile Beach are located nearby.

3-4 Night Vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast

Shangri-La Boutique Bed & Breakfast

4 out of 5
Price was $1,363, price is now $1,062 per person
$1,062
per person
Jan 7 - Jan 11
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
The Grove and The Grove Too

The Grove and The Grove Too

5 out of 5
Price was $2,047, price is now $1,211 per person
$1,211
per person
Jan 7 - Jan 11
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

2.5 out of 5
Price was $1,479, price is now $1,113 per person
$1,113
per person
Jan 7 - Jan 11
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
ONE GT Grand Cayman

ONE GT Grand Cayman

4.5 out of 5
Price was $1,873, price is now $1,439 per person
$1,439
per person
Jan 7 - Jan 11
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)

5-7 Night Vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.
The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

3.5 out of 5
Save 100% on your flight
Price was $1,809, price is now $934 per person
$934
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
The Grove and The Grove Too

The Grove and The Grove Too

5 out of 5
Save 100% on your flight
Price was $2,293, price is now $1,347 per person
$1,347
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
ONE GT Grand Cayman

ONE GT Grand Cayman

4.5 out of 5
Save 100% on your flight
Price was $2,178, price is now $1,607 per person
$1,607
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Save 100% on your flight
Price was $4,659, price is now $3,561 per person
$3,561
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)

Cheap Hotel Deals in Cayman Islands

The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
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. ...
Opens in a new windowThe Ritz-Carlton, Grand Cayman
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

2.5 out of 5
KY1-1206, Seven Mile Beach Corridor Seven Mile Beach Grand Cayman
Book a stay at this family-friendly hotel in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and 2 meeting rooms. Popular attractions Governor's ...
Opens in a new windowGovernors Village Seven Mile Beach Corridor
Grand Cayman Marriott Beach Resort

Grand Cayman Marriott Beach Resort

4.5 out of 5
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 ...
Opens in a new windowGrand Cayman Marriott Beach Resort
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The Locale Hotel Grand Cayman

The Locale Hotel Grand Cayman

3.5 out of 5
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 ...
Opens in a new windowThe Locale Hotel Grand Cayman
The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
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 ...
Opens in a new windowThe Westin Grand Cayman Seven Mile Beach Resort & Spa
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
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 Governor's ...
Opens in a new windowHotel Indigo Grand Cayman by IHG
The Grove and The Grove Too

The Grove and The Grove Too

5 out of 5
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 Governor's ...
Opens in a new windowThe Grove and The Grove Too
Hampton by Hilton Grand Cayman Seven Mile Beach

Hampton by Hilton Grand Cayman Seven Mile Beach

4 out of 5
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. ...
Opens in a new windowHampton by Hilton Grand Cayman Seven Mile Beach
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.

Porter Airlines
Tue, Dec 15 - Tue, Dec 22
YYZ
Pearson Intl.
GCM
Owen Roberts Intl.
$388 Roundtrip, found 1 day ago
$388
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Tue, Dec 15 from Pearson Intl. to Owen Roberts Intl., returning Tue, Dec 22, priced at $388 found 1 day ago
American Airlines
Fri, Jan 29 - Wed, Feb 3
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$402 Roundtrip, found 9 hours ago
$402
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Fri, Jan 29 from Logan Intl. to Owen Roberts Intl., returning Wed, Feb 3, priced at $402 found 9 hours ago
Air Canada
Wed, Dec 2 - Wed, Dec 9
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$469 Roundtrip, found 8 hours ago
$469
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Wed, Dec 2 from O'Hare Intl. to Owen Roberts Intl., returning Wed, Dec 9, priced at $469 found 8 hours ago
JetBlue Airways
Fri, Jan 8 - Sat, Jan 16
JFK
John F. Kennedy Intl.
GCM
Owen Roberts Intl.
$481 Roundtrip, found 2 days ago
$481
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Jan 8 from John F. Kennedy Intl. to Owen Roberts Intl., returning Sat, Jan 16, priced at $481 found 2 days ago