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Cayman Islands vacations

Price found within the past 48 hours. Click for updated prices.
On The Bay

On The Bay

4 out of 5
per person
Jul 7 - Jul 11
found 19 hours ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
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
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to George Town (GCM)
Plantation Village 2 Bed / 2 Bath

Plantation Village 2 Bed / 2 Bath

3.5 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Ocean Paradise

Ocean Paradise

4 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
ONE Canal Point

ONE Canal Point

3.5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

3.5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Caribbean Club Luxury Condo Hotel

Caribbean Club Luxury Condo Hotel

5 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)

3-night Cayman Islands vacations

Price found within the past 48 hours. Click for updated prices.
Morritts Tortuga Club

Morritts Tortuga Club

3.5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Ocean Paradise

Ocean Paradise

4 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
ONE Canal Point

ONE Canal Point

3.5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

3.5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Kimpton Seafire Resort + Spa, an IHG Hotel

Kimpton Seafire Resort + Spa, an IHG Hotel

5 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
BP Beach Concierge Island Retro Chic

BP Beach Concierge Island Retro Chic

2 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
VIDA Cayman

VIDA Cayman

3 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
Botanica

Botanica

4 out of 5
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)

4-night Cayman Islands vacations

Price found within the past 48 hours. Click for updated prices.
Morritts Tortuga Club

Morritts Tortuga Club

3.5 out of 5
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Save 100% on your flight
per person
Jul 7 - Jul 11
found 19 hours ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
On The Bay

On The Bay

4 out of 5
per person
Jul 7 - Jul 11
found 19 hours ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
ONE Canal Point

ONE Canal Point

3.5 out of 5
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

3.5 out of 5
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Sunset Cove

Sunset Cove

3.5 out of 5
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Caribbean Club Luxury Condo Hotel

Caribbean Club Luxury Condo Hotel

5 out of 5
Save 100% on your flight
per person
Jul 7 - Jul 11
found 19 hours ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Kimpton Seafire Resort + Spa, an IHG Hotel

Kimpton Seafire Resort + Spa, an IHG Hotel

5 out of 5
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Botanica

Botanica

4 out of 5
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)

5-night Cayman Islands vacations

Price found within the past 48 hours. Click for updated prices.
Morritts Tortuga Club

Morritts Tortuga Club

3.5 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Plantation Village 2 Bed / 2 Bath

Plantation Village 2 Bed / 2 Bath

3.5 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Sunset Cove

Sunset Cove

3.5 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Hampton by Hilton Grand Cayman Seven Mile Beach

Hampton by Hilton Grand Cayman Seven Mile Beach

4 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
ONE Canal Point

ONE Canal Point

3.5 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

3.5 out of 5
per person
Jul 17 - Jul 22
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)

6-7 night Cayman Islands vacations

Price found within the past 48 hours. Click for updated prices.
Morritts Tortuga Club

Morritts Tortuga Club

3.5 out of 5
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
Kimpton Seafire Resort + Spa, an IHG Hotel

Kimpton Seafire Resort + Spa, an IHG Hotel

5 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
Hampton by Hilton Grand Cayman Seven Mile Beach

Hampton by Hilton Grand Cayman Seven Mile Beach

4 out of 5
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
ONE Canal Point

ONE Canal Point

3.5 out of 5
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

3.5 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
Caribbean Club Luxury Condo Hotel

Caribbean Club Luxury Condo Hotel

5 out of 5
Save 100% on your flight
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Seven Mile Beach Resort & Club

Seven Mile Beach Resort & Club

3 out of 5
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
per person
Jul 6 - Jul 13
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to George Town (GCM)

Top places to visit in Cayman Islands

FlightsFlightsHotelsHotels

Seven Mile Beach

Seven Mile Beach

Flight deals to Cayman Islands

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jul 4 - Sat, Jul 13
YUL
Montreal
GCM
George Town
$303 Roundtrip, found 3 days ago
$303
Roundtrip
found 3 days ago
Select United flight, departing Thu, Jul 4 from Montreal to George Town, returning Sat, Jul 13, priced at $303 found 3 days ago
Mon, Jun 10 - Wed, Jun 12
JFK
New York
GCM
George Town
$324 Roundtrip, found 1 day ago
$324
Roundtrip
found 1 day ago
Select Cayman Airways flight, departing Mon, Jun 10 from New York to George Town, returning Wed, Jun 12, priced at $324 found 1 day ago
Tue, Jul 16 - Mon, Jul 22
LGA
New York
GCM
George Town
$335 Roundtrip, found 7 hours ago
$335
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Jul 16 from New York to George Town, returning Mon, Jul 22, priced at $335 found 7 hours ago

Top rated hotels for your Cayman Islands vacation

The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
8.34 mi from city center
The price is $709 per night
$709
per night
Jun 8 - Jun 9
When you stay at The Ritz-Carlton, Grand Cayman in Seven Mile Beach, you'll be on the beach, a 1-minute drive from Seven Mile Beach and 8 minutes from Port of Georgetown.
Pool
Hot Tub
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road, Po Box 30371, Seven Mile Beach, Grand Cayman
8.41 mi from city center
The price is $314 per night
$314
per night
Jun 4 - Jun 5
Located in Seven Mile Beach, Grand Cayman Marriott Resort is on the waterfront, a 4-minute walk from Seven Mile Beach and 12 minutes by foot from Camana Bay.
Pool
Hot Tub
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, P.O. Box 30620, Seven Mile Beach, Grand Cayman
8.38 mi from city center
The price is $649 per night
$649
per night
Jun 24 - Jun 25
When you stay at The Westin Grand Cayman Seven Mile Beach Resort & Spa in Seven Mile Beach, you'll be on the waterfront, within a 5-minute drive of The Strand Shopping Center and Galleria Plaza.
Pool
On private beach
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.