Old Man Bay Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Old Man Bay Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Reef Beach Resort, East End, Grand Cayman
$1,573
per person
Nov 26 - Dec 3
found 4 hours ago
Roundtrip non-stop flight included
Pensacola (PNS) 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.
Point West Premier Rentals
Northwest Point
$2,327
per person
Nov 26 - Dec 3
found 4 hours ago
Roundtrip non-stop flight included
Pensacola (PNS) 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.
Black Urchin
$11,307
per person
Nov 26 - Dec 3
found 4 hours ago
Roundtrip non-stop flight included
Pensacola (PNS) 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.
Club Suites at Rum Point
$3,460
per person
Nov 26 - Dec 3
found 4 hours ago
Roundtrip non-stop flight included
Pensacola (PNS) 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.
Little slice of heaven. The condo is spacious and well appointed. They’ve thought of everything. Restaurant is very good.
Reviewed on Sep 6, 2026
Cayman Luxury Rentals at Ocean Paradise
$1,929
per person
Nov 26 - Dec 3
found 4 hours ago
Roundtrip non-stop flight included
Pensacola (PNS) 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.
Family friendly, very equipped accommodation. Caring and quick responsive staff. Would definitely recommend the place.
Reviewed on Jul 11, 2026
Governors Village Seven Mile Beach Corridor
$1,629
per person
Nov 26 - Dec 3
found 4 hours ago
Roundtrip non-stop flight included
Pensacola (PNS) to George Town (GCM)
Book a stay at this family-friendly apartment in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and 2 meeting rooms. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
The floors were a bit dirty and we did find a few hairs in our bedsheetswhen we first got there, but overall a very comfortable stay. Wish we had a balcony so we could hang out stuff to dry, but that's really not something that can be remedied. Loved the convenience of the cafe downstairs and the pool set up. It was a very cozy and quiet stay, which was ideal.
Reviewed on Sep 13, 2026
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See all available trips from Columbus to Old Man Bay
View all tripsTop Hotel Deals
On The Bay
67 Old Robin Rd North Side North Side
Book a stay at this beach condo in North Side. Enjoy free WiFi, free parking, and private pools. Popular attractions Grand Cayman Beaches and Cayman Crystal ...
The Place
110 Old Robin Rd Old Man Bay North Side
Book a stay at this business-friendly apartment in North Side. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Grand Cayman Beaches ...
The Ritz-Carlton, Grand Cayman
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. ...
Kimpton Seafire Resort + Spa by IHG
60 Tanager Way Seven Mile Beach Grand Cayman
Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...
The Locale Hotel Grand Cayman
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 ...
Hotel Indigo Grand Cayman by IHG
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 Port of ...
Grand Cayman Marriott Beach Resort.
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 ...
The Westin Grand Cayman Seven Mile Beach Resort & Spa
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 ...
Governors Village Seven Mile Beach Corridor
KY1-1206, Seven Mile Beach Corridor Seven Mile Beach Grand Cayman
Book a stay at this family-friendly apartment in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and 2 meeting rooms. Popular attractions Seven ...
The Reef Beach Resort - All Inclusive - East End, Grand Cayman
2221 Queens Highway Colliers Bay East End Grand Cayman
Book a stay at this beach property in East End. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Hampton by Hilton Grand Cayman Seven Mile Beach
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. ...
The Sunshine Hotel and Suites
1465 Esterley Tibbetts Seven Mile Beach Grand Cayman
Book a stay at this beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
The Grove
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 a full-service spa. Popular attractions Seven Mile Beach and Port ...
Palm Heights
747 West Bay Road Seven Mile Beach
Book a stay at this luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
ONE GT Grand Cayman
63 Goring Ave George Town George Town
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 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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Sep 18 - Sat, Sep 19
YYZ
Pearson Intl.
GCM
Owen Roberts Intl.
$314
Roundtrip
found 4 days ago
Thu, Oct 29 - Sat, Oct 31
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$393
Roundtrip
found 2 days ago
Tue, Oct 27 - Fri, Oct 30
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$419
Roundtrip
found 2 days ago
Thu, Oct 29 - Wed, Nov 4
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$433
Roundtrip
found 2 days ago
Wed, Sep 16 - Thu, Sep 17
MIA
Miami Intl.
GCM
Owen Roberts Intl.
$543
Roundtrip
found 6 days ago
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