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Search results; Over 1,000 homes in Old Man Bay

Top guest favourite
Townhouse in Old Man Bay
Your Oceanside Retreat Awaits!
2 bedrooms, 3 beds, 2 private bathrooms
15–20 Sept
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4.92 out of 5 average rating, 64 reviews
Guest favourite
Flat in North Side
On The Bay 310 - Enjoy the View
2 bedrooms, 2 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Old Man Bay
Beach House & Cottage - The Bay
5 bedrooms, 10 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Old Man Bay
Coral Cottage - Beach Front w/ Private Pool
3 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
Superhost
Apartment in Old Man Bay
Silver Reef 1 Luxury 2BR Beachfront Retreat with P
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.73 out of 5 average rating, 15 reviews
Guest favourite
Apartment in North Side
Northern Lights 6 - 2BR/2.5BA Oceanfront & Pool
2 bedrooms, 3 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Apartment in North Side
Spacious 2-Bed Beachfront Condo w/ Heated Pool
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Old Man Bay
Sail Away- bright modern cozy apt in North Side
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 6 reviews
Villa in North Side
Calypso Blue | 6BR Oceanfront Villa | Grand Cayman
6 bedrooms, 8 beds, 4.5 bathrooms
15–20 Sept
Guest favourite
Apartment in North Side
Silver Reef #3 - 2 BR LUXE Oceanfront & Pool
2 bedrooms, 2 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 17 reviews
Luxe
Home in North Side
Luxury Beachview Retreat, Cayman Islands
4 bedrooms, 7 beds, 4.5 bathrooms
23–28 Sept
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in North Side
Private, quiet oceanfront home 360 screened porch.
3 bedrooms, 5 beds, 3 bathrooms
10–15 Oct
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Villa in North Side
Villa at the Sea Front
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.95 out of 5 average rating, 61 reviews
Top guest favourite
Home in Rum Point
Whispering Kai: beach home on Bio Bay, Cayman Kai
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in North Side
Oceanfront Dreamsicle Villa w/Outdoor Living Area
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
4.97 out of 5 average rating, 58 reviews
Top guest favourite
Apartment in North Side
Northern Lights 3 - 2BR/2.5BA Oceanfront & Pool
2 bedrooms, 4 beds, 2.5 bathrooms
15–20 Sept
4.95 out of 5 average rating, 21 reviews
Superhost
Flat in Bodden Town
Suncoast Apartments Grand Cayman - Unit # 1
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.83 out of 5 average rating, 147 reviews
Top guest favourite
Home in North Side
North Side Grand Cayman Beachfront Villa
4 bedrooms, 6 beds, 6 bathrooms
12–17 Jan
4.99 out of 5 average rating, 117 reviews
Guest favourite
Home in Cayman Islands
Parrot‑ise 4BR Oceanfront Villa - Pool & Tiki Bar
4 bedrooms, 4 beds, 3.5 bathrooms
15–20 Sept
4.75 out of 5 average rating, 28 reviews