Cheap Vacations in Cayman Islands

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Cayman Islands vacations

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 $1,252, price is now $890 per person
$890
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
VIDA Cayman

VIDA Cayman

4 out of 5
Price was $2,612, price is now $1,514 per person
$1,514
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Price was $2,771, price is now $1,865 per person
$1,865
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Price was $3,955, price is now $2,732 per person
$2,732
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Cayman Luxury Rentals at The Grove

Cayman Luxury Rentals at The Grove

3.5 out of 5
Price was $1,917, price is now $1,399 per person
$1,399
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Price was $4,454, price is now $3,267 per person
$3,267
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

3.5 out of 5
Price was $1,712, price is now $1,312 per person
$1,312
per person
Mar 1 - Mar 6
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to George Town (GCM)
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
Price was $1,602, price is now $1,255 per person
$1,255
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
Price was $1,946, price is now $1,526 per person
$1,526
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Luxury Penthouse Condo With 360 Oceanviews

Luxury Penthouse Condo With 360 Oceanviews

2 out of 5
Save 100% on your flight
Price was $15,017, price is now $11,866 per person
$11,866
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)

3-night Cayman Islands vacations

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 $921, price is now $753 per person
$753
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
VIDA Cayman

VIDA Cayman

4 out of 5
Save 100% on your flight
Price was $1,846, price is now $1,117 per person
$1,117
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $2,958, price is now $1,858 per person
$1,858
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Save 100% on your flight
Price was $2,129, price is now $1,362 per person
$1,362
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $2,915, price is now $2,062 per person
$2,062
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
Save 100% on your flight
Price was $12,425, price is now $8,836 per person
$8,836
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Ocean Paradise

Ocean Paradise

4 out of 5
Price was $1,538, price is now $1,256 per person
$1,256
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
Price was $1,201, price is now $986 per person
$986
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was $1,392, price is now $1,159 per person
$1,159
per person
Feb 19 - Feb 22
found 19 hours ago
Roundtrip flight included
New York (NYC) to Little Cayman (LYB)
Kiboko

Kiboko

3.5 out of 5
Price was $5,106, price is now $4,283 per person
$4,283
per person
Mar 12 - Mar 15
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Coconut Bay 126 in West Bay

Coconut Bay 126 in West Bay

2 out of 5
Save 100% on your flight
Price was $3,161, price is now $2,668 per person
$2,668
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Compass Point Dive Resort

Compass Point Dive Resort

3.5 out of 5
Price was $1,219, price is now $1,040 per person
$1,040
per person
Feb 17 - Feb 20
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)

4-night Cayman Islands vacations

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 $1,252, price is now $890 per person
$890
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
VIDA Cayman

VIDA Cayman

4 out of 5
Price was $2,612, price is now $1,514 per person
$1,514
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Price was $2,771, price is now $1,865 per person
$1,865
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Price was $3,955, price is now $2,732 per person
$2,732
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Cayman Luxury Rentals at The Grove

Cayman Luxury Rentals at The Grove

3.5 out of 5
Price was $1,917, price is now $1,399 per person
$1,399
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Price was $4,454, price is now $3,267 per person
$3,267
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

3.5 out of 5
Save 100% on your flight
Price was $1,355, price is now $1,004 per person
$1,004
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Compass Point Dive Resort

Compass Point Dive Resort

3.5 out of 5
Save 100% on your flight
Price was $1,528, price is now $1,157 per person
$1,157
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
The Grand Caymanian Resort

The Grand Caymanian Resort

3.5 out of 5
Save 100% on your flight
Price was $2,536, price is now $1,969 per person
$1,969
per person
Mar 4 - Mar 8
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
Price was $1,602, price is now $1,255 per person
$1,255
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
Price was $1,946, price is now $1,526 per person
$1,526
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was $1,542, price is now $1,226 per person
$1,226
per person
Feb 18 - Feb 22
found 24 hours ago
Roundtrip flight included
New York (JFK) to Little Cayman (LYB)

5-night Cayman Islands vacations

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 $1,430, price is now $995 per person
$995
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
VIDA Cayman

VIDA Cayman

4 out of 5
Price was $1,967, price is now $1,187 per person
$1,187
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Price was $2,656, price is now $1,774 per person
$1,774
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Price was $4,628, price is now $3,232 per person
$3,232
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
Price was $1,709, price is now $1,199 per person
$1,199
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

3.5 out of 5
Price was $1,712, price is now $1,312 per person
$1,312
per person
Mar 1 - Mar 6
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
Price was $2,197, price is now $1,691 per person
$1,691
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
Price was $1,661, price is now $1,280 per person
$1,280
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Luxury Penthouse Condo With 360 Oceanviews

Luxury Penthouse Condo With 360 Oceanviews

2 out of 5
Save 100% on your flight
Price was $10,773, price is now $8,524 per person
$8,524
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
Seabreeze 8 - Luxury 4-bedroom on Seven Mile Beach

Seabreeze 8 - Luxury 4-bedroom on Seven Mile Beach

2.5 out of 5
Save 100% on your flight
Price was $6,523, price is now $5,206 per person
$5,206
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip flight included
New York (JFK) to George Town (GCM)
Kiboko

Kiboko

3.5 out of 5
Save 100% on your flight
Price was $8,520, price is now $6,844 per person
$6,844
per person
Mar 1 - Mar 6
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to George Town (GCM)
The Grove

The Grove

5 out of 5
Price was $1,923, price is now $1,547 per person
$1,547
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)

6-7 night Cayman Islands vacations

Price found within the past 48 hours. Click for updated prices.
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

3.5 out of 5
Save 100% on your flight
Price was $1,608, price is now $1,199 per person
$1,199
per person
Feb 26 - Mar 4
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
VIDA Cayman

VIDA Cayman

4 out of 5
Price was $5,276, price is now $3,186 per person
$3,186
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Price was $3,491, price is now $2,289 per person
$2,289
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
Price was $2,757, price is now $1,823 per person
$1,823
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Shangri-La Boutique Bed & Breakfast

Shangri-La Boutique Bed & Breakfast

4 out of 5
Price was $1,869, price is now $1,246 per person
$1,246
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
Price was $2,154, price is now $1,629 per person
$1,629
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
Price was $2,720, price is now $2,072 per person
$2,072
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Price was $6,485, price is now $4,946 per person
$4,946
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Ocean Paradise

Ocean Paradise

4 out of 5
Price was $3,319, price is now $2,596 per person
$2,596
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Luxury Penthouse Condo With 360 Oceanviews

Luxury Penthouse Condo With 360 Oceanviews

2 out of 5
Save 100% on your flight
Price was $15,017, price is now $11,866 per person
$11,866
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
The Grove

The Grove

5 out of 5
Price was $2,553, price is now $2,026 per person
$2,026
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to George Town (GCM)
Villas of the Galleon

Villas of the Galleon

2.5 out of 5
Price was $4,775, price is now $3,825 per person
$3,825
per person
Mar 4 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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, Feb 26 - Thu, Mar 5
EWR
New York
GCM
Grand Cayman
$278 Roundtrip, found 18 hours ago
$278
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Thu, Feb 26 from New York to Grand Cayman, returning Thu, Mar 5, priced at $278 found 18 hours ago
Thu, Feb 19 - Wed, Feb 25
JFK
New York
GCM
Grand Cayman
$311 Roundtrip, found 1 day ago
$311
Roundtrip
found 1 day ago
Select Cayman Airways flight, departing Thu, Feb 19 from New York to Grand Cayman, returning Wed, Feb 25, priced at $311 found 1 day ago
Sat, Nov 14 - Tue, Nov 24
BOS
Boston
GCM
Grand Cayman
$312 Roundtrip, found 2 days ago
$312
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Nov 14 from Boston to Grand Cayman, returning Tue, Nov 24, priced at $312 found 2 days ago

Top rated hotels for your Cayman Islands vacation

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
8.62 mi from city center
$560 nightly
The price is $626 total per night
$626 total
Jan 20 - Jan 21
Total with taxes and fees
When you stay at Hotel Indigo Grand Cayman by IHG in Seven Mile Beach, you'll be near the beach, within a 5-minute walk of Seven Mile Beach and Grand Cayman Beaches.
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

4.5 out of 5
389 West Bay Road Seven Mile Beach Grand Cayman
8.41 mi from city center
$552 nightly
The price is $616 total per night
$616 total
Jan 26 - Jan 27
Total with taxes and fees
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.
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road Seven Mile Beach Grand Cayman
8.34 mi from city center
$1,582 nightly
The price is $1,771 total per night
$1,771 total
Jan 31 - Feb 1
Total with taxes and fees
With a stay at The Ritz-Carlton, Grand Cayman in Seven Mile Beach, you'll be on the beach, a 2-minute walk from Seven Mile Beach and a 3-minute drive from Grand Cayman Beaches.
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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.