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Old Man Bay Vacation Packages

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Old Man Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Villas of the Galleon 4

Villas of the Galleon 4

2 out of 5
Save 100% on your flight
Price was $1,552, price is now $1,259 per person
$1,259
per person
Oct 26 - Oct 30
found 2 days ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
Book a stay at this beach apartment in Seven Mile Beach. Enjoy free parking and a beach locale. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

Point West Premier Rentals

Point West Premier Rentals

4 out of 5
Price was $2,761, price is now $1,925 per person
$1,925
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to George Town (GCM)
Stay at this aparthotel in West Bay. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

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 $10,685, price is now $8,076 per person
$8,076
per person
Nov 28 - Dec 5
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
Stay at this apartment in Seven Mile Beach. Enjoy free parking, a beach locale, and a fitness center. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

Cayman Luxury Rentals at Sunset Cove

Cayman Luxury Rentals at Sunset Cove

3.5 out of 5
Save 100% on your flight
Price was $2,937, price is now $2,243 per person
$2,243
per person
Dec 2 - Dec 6
found 14 hours ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
Book a stay at this beach vacation home 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.
Couldn’t have enjoyed our stay more. This place is a hidden secret.

Reviewed on Apr 13, 2026

Luxury Penthouse Condo With 360 Oceanviews

Luxury Penthouse Condo With 360 Oceanviews

2 out of 5
Save 100% on your flight
Price was $4,259, price is now $3,328 per person
$3,328
per person
Oct 26 - Oct 30
found 2 days ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
Stay at this apartment in Seven Mile Beach. Enjoy free parking and a beach locale. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

Villas of the Galleon 6

Villas of the Galleon 6

2 out of 5
Save 100% on your flight
Price was $2,390, price is now $1,894 per person
$1,894
per person
Nov 26 - Nov 29
found 20 hours ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
Book a stay at this beach apartment in Seven Mile Beach. Enjoy free parking and a beach locale. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.

Cocoplum 10 in George Town

Cocoplum 10 in George Town

2 out of 5
Save 100% on your flight
Price was $2,503, price is now $1,987 per person
$1,987
per person
Nov 26 - Nov 29
found 20 hours ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
Book a stay at this beach apartment in Seven Mile Beach. Enjoy free parking, a beach locale, and a garden. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.

Sprat Bay Luxury Villa - Private Beach and Pool

Sprat Bay Luxury Villa - Private Beach and Pool

2 out of 5
Price was $11,225, price is now $9,044 per person
$9,044
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip non-stop flight included
Denver (DEN) to George Town (GCM)
Book a stay at this beach vacation home in George Town. Enjoy free parking, a beach locale, and a garden. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.

Old Man Bay Vacation Packages 3-4 Night Stays

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 $1,140, price is now $637 per person
$637
per person
Oct 26 - Oct 30
found 2 days ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
Save 100% on your flight
Price was $1,702, price is now $1,111 per person
$1,111
per person
Oct 26 - Oct 30
found 2 days ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
Point West Premier Rentals

Point West Premier Rentals

4 out of 5
Northwest Point
Save 100% on your flight
Price was $1,529, price is now $1,000 per person
$1,000
per person
Nov 26 - Nov 29
found 20 hours ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
Price was $5,856, price is now $3,993 per person
$3,993
per person
Oct 26 - Oct 30
found 2 days ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)

Old Man Bay Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Point West Premier Rentals

Point West Premier Rentals

4 out of 5
Northwest Point
Price was $2,761, price is now $1,925 per person
$1,925
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to George Town (GCM)
Cayman Luxury Rentals at Sunset Cove

Cayman Luxury Rentals at Sunset Cove

3.5 out of 5
Save 100% on your flight
Price was $4,239, price is now $3,109 per person
$3,109
per person
Dec 2 - Dec 8
found 14 hours ago
Roundtrip flight included
Miami (MIA) 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 $10,685, price is now $8,076 per person
$8,076
per person
Nov 28 - Dec 5
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to George Town (GCM)
Cocoplum 10 in George Town

Cocoplum 10 in George Town

2 out of 5
Save 100% on your flight
Price was $4,094, price is now $3,118 per person
$3,118
per person
Dec 2 - Dec 8
found 14 hours ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)

Top Flight Deals

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

Air Canada
Thu, Oct 15 - Fri, Oct 30
YYZ
Pearson Intl.
GCM
Owen Roberts Intl.
$251 Roundtrip, found 6 days ago
$251
Roundtrip
found 6 days ago
Select Air Canada flight, departing Thu, Oct 15 from Pearson Intl. to Owen Roberts Intl., returning Fri, Oct 30, priced at $251 found 6 days ago
Cayman Airways
Thu, Oct 8 - Mon, Oct 19
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$287 Roundtrip, found 1 day ago
$287
Roundtrip
found 1 day ago
Select Cayman Airways flight, departing Thu, Oct 8 from Miami Intl. to Owen Roberts Intl., returning Mon, Oct 19, priced at $287 found 1 day ago
Air Canada
Thu, Sep 17 - Mon, Sep 21
LGA
LaGuardia
GCM
Owen Roberts Intl.
$364 Roundtrip, found 2 days ago
$364
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Sep 17 from LaGuardia to Owen Roberts Intl., returning Mon, Sep 21, priced at $364 found 2 days ago
American Airlines
Mon, Oct 5 - Fri, Oct 9
EWR
Newark Liberty Intl. Airport
GCM
Owen Roberts Intl.
$435 Roundtrip, found 2 days ago
$435
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Oct 5 from Newark Liberty Intl. Airport to Owen Roberts Intl., returning Fri, Oct 9, priced at $435 found 2 days ago