Vacations in the Cayman Islands

Vacations in the Cayman Islands

2 travelers

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$752 - $1,609$1,609 - $2,465$2,465 - $3,322$3,322 - $4,178$4,178+ per night

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Most popular the Cayman Islands flight and hotel deals

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Regal Beach Club #322 - George Town - Bedroom
Regal Beach Club #322 - George Town - Bedroom
Regal Beach Club #322
9.8 Wonderful
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,835
Regal Beach Club - George Town - Balcony
Regal Beach Club - George Town - Balcony
Regal Beach Club
9 Wonderful
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,217
The Locale Hotel Grand Cayman - West Bay - Building
The Locale Hotel Grand Cayman - West Bay - Building
The Locale Hotel Grand Cayman
8.7 Very good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Breakfast
3 nights + flight
$824
Holiday Inn Resort Grand Cayman by IHG - George Town - Pool
Holiday Inn Resort Grand Cayman by IHG - George Town - Pool
Holiday Inn Resort Grand Cayman by IHG
7.8 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$771
The Grove - West Bay - Beach
The Grove - West Bay - Beach
The Grove
9.8 Wonderful
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,014
Sunshine Suites Resort - George Town - Beach
Sunshine Suites Resort - George Town - Beach
Sunshine Suites Resort
7.5 Good
Parking
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$910
The Grand Caymanian Resort - George Town - Pool
The Grand Caymanian Resort - George Town - Pool
The Grand Caymanian Resort
7.5 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$799
Villas of the Galleon - George Town - Living room
Villas of the Galleon - George Town - Living room
Villas of the Galleon
9.4 Wonderful
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,623
Governors Village - George Town - Bedroom
Governors Village - George Town - Bedroom
Governors Village
9.3 Wonderful
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$858
Seven Mile Beach Resort - West Bay - Pool
Seven Mile Beach Resort - West Bay - Pool
Seven Mile Beach Resort
8.8 Very good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$880
Hotel Indigo Grand Cayman By IHG - West Bay - Bedroom
Hotel Indigo Grand Cayman By IHG - West Bay - Bedroom
Hotel Indigo Grand Cayman By IHG
9.5 Wonderful
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,156
Grand Cayman Marriott Resort - George Town - Lounge
Grand Cayman Marriott Resort - George Town - Lounge
Grand Cayman Marriott Resort
8.5 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,223
Sunset Cove - George Town - Beach
Sunset Cove - George Town - Beach
Sunset Cove
Free Wi-Fi
Paris Charles de Gaulle
Meals not included
3 nights + flight
$2,118
The Westin Grand Cayman Seven Mile Beach Resort & Spa - George Town - Patio
The Westin Grand Cayman Seven Mile Beach Resort & Spa - George Town - Patio
The Westin Grand Cayman Seven Mile Beach Resort & Spa
8.3 Very good
Parking
Pool
Pet friendly
Spa
London Heathrow
Meals not included
3 nights + flight
$1,532
The Ritz-Carlton Grand Cayman - George Town - Balcony
The Ritz-Carlton Grand Cayman - George Town - Balcony
The Ritz-Carlton Grand Cayman
9.2 Wonderful
Parking
Free Wi-Fi
Pool
Pet friendly
London Heathrow
Meals not included
3 nights + flight
$1,904
Hampton by Hilton Grand Cayman Seven Mile Beach - George Town - Lounge
Hampton by Hilton Grand Cayman Seven Mile Beach - George Town - Lounge
Hampton by Hilton Grand Cayman Seven Mile Beach
8.6 Very good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Breakfast
3 nights + flight
$752

When to book a vacation in the Cayman Islands

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Tips for finding the Cayman Islands package deals

  • There are loads of types of vacations in the Cayman Islands and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $1,021; Family vacation $978; Romantic vacation $991.

Where to stay in the Cayman Islands

Our map will help you find the perfect place to stay for your vacation in the Cayman Islands by showing you the exact location of each hotel.

Everything you need to know for your vacation in the Cayman Islands

the Cayman Islands vacation information

Top vacation (Flight+Hotel)$1,021
Family vacation (Flight+Hotel)$978
Romantic vacation (Flight+Hotel)$991