Old Man Bay Vacations

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Top Hotel Deals

On The Bay

On The Bay

4 out of 5
67 Old Robin Rd North Side North Side
0.36 km from city center
Book a stay at this beach condo in North Side. Enjoy free WiFi, free parking, and private pools. Popular attractions Cayman Crystal Caves and Babylon (Dive Site) ...
The Place

The Place

4 out of 5
110 Old Robin Rd Old Man Bay North Side
0.39 km from city center
Book a stay at this business-friendly apartment in North Side. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Cayman Crystal Caves ...
The Locale Hotel Grand Cayman

The Locale Hotel Grand Cayman

3.5 out of 5
455 West Bay Road, Seven Mile Beach, Grand Cayman
21.85 km from city center
Stay at this 3.5-star business-friendly hotel in Seven Mile Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
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
21.44 km from city center
Stay at this 5-star luxury resort in Seven Mile Beach. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff in our ...
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
21.74 km from city center
Stay at this 4.5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free valet parking, and 4 restaurants. Popular attractions Seven Mile Beach and Port ...
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
21.97 km from city center
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the ...
Hampton by Hilton Grand Cayman Seven Mile Beach

Hampton by Hilton Grand Cayman Seven Mile Beach

4 out of 5
22 Piper Way Seven Mile Beach
22.01 km from city center
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. ...
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
60 Tanager Way, Seven Mile Beach, Grand Cayman
21.71 km from city center
Stay at this 5-star 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 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
21.42 km from city center
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy a full-service spa, 6 restaurants, and a private beach. Our guests praise the helpful staff and ...
The Grove

The Grove

5 out of 5
1350 W Bay Rd, Seven Mile Beach, West Bay
21.49 km from city center
Stay at this 5-star luxury aparthotel in Seven Mile Beach. Enjoy free WiFi, free parking, and 3 restaurants. Popular attractions Seven Mile Beach and Port of ...
Governors Village Seven Mile Beach Corridor

Governors Village Seven Mile Beach Corridor

3.5 out of 5
KY1-1206, Seven Mile Beach Corridor Seven Mile Beach Grand Cayman
21.26 km from city center
Book a stay at this family-friendly apartment in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and a garden. Popular attractions Seven Mile ...
Wyndham Reef Resort - All Inclusive

Wyndham Reef Resort - All Inclusive

3.5 out of 5
2221 Queens Highway Colliers Bay, East End, Grand Cayman
8.9 km from city center
Stay at this 3.5-star beach property in East End. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Seven Mile Beach Resort & Club

Seven Mile Beach Resort & Club

3 out of 5
19 D Piper Way, West Bay Road Seven Mile Beach Grand Cayman
21.98 km from city center
Book a stay at this beach hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a free beach shuttle. Our guests praise the helpful staff in our reviews. ...
Cobalt Coast Resort

Cobalt Coast Resort

3.5 out of 5
18-A Sea Fan Drive, West Bay, Grand Cayman
24.5 km from city center
Stay at this 3.5-star beach resort in West Bay. Enjoy free WiFi, free parking, and a private beach. Popular attractions Seven Mile Beach and Hell are located ...
Sunshine Suites Resort

Sunshine Suites Resort

4 out of 5
1465 Esterley Tibbetts, Seven Mile Beach, Grand Cayman
21.25 km from city center
Stay at this 4-star beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service, and beach cabanas (surcharge). Our guests praise the restaurant ...
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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.

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.

Delta
Mon, Feb 23 - Wed, Feb 25
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$354 Roundtrip, found 3 days ago
$354
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Feb 23 from O'Hare Intl. to Owen Roberts Intl., returning Wed, Feb 25, priced at $354 found 3 days ago
American Airlines
Sun, Feb 22 - Thu, Feb 26
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$384 Roundtrip, found 3 days ago
$384
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Feb 22 from O'Hare Intl. to Owen Roberts Intl., returning Thu, Feb 26, priced at $384 found 3 days ago
JetBlue Airways
Mon, Feb 23 - Sun, Mar 1
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$457 Roundtrip, found 3 days ago
$457
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Feb 23 from O'Hare Intl. to Owen Roberts Intl., returning Sun, Mar 1, priced at $457 found 3 days ago
Air Canada
Mon, Feb 23 - Tue, Mar 3
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$477 Roundtrip, found 3 days ago
$477
Roundtrip
found 3 days ago
Select Air Canada flight, departing Mon, Feb 23 from O'Hare Intl. to Owen Roberts Intl., returning Tue, Mar 3, priced at $477 found 3 days ago
United
Sun, Feb 22 - Sun, Mar 1
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$480 Roundtrip, found 3 days ago
$480
Roundtrip
found 3 days ago
Select United flight, departing Sun, Feb 22 from O'Hare Intl. to Owen Roberts Intl., returning Sun, Mar 1, priced at $480 found 3 days ago