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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
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
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
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
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
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
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
Top guest favourite
Apartment in Cayman Islands
On the Bay #103 - Northside 3BR Beach Condo & Pool
3 bedrooms, 4 beds, 3 bathrooms
3–8 Dec
4.89 out of 5 average rating, 28 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
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
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
Cottage in Savannah
John John's Hideaway
1 bedroom, 1 bed, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 245 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
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
Guest favourite
Apartment in Old Man Bay
Northern Lights 4 - 2BR/2.5BA Oceanfront & Pool
2 bedrooms, 3 beds, 2.5 bathrooms
15–20 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Guest suite in George Town
Paradise Escape-Charming Oceanfront Guest Suite
1 bedroom, 1 queen bed, 1 bathroom
10–15 Oct
4.97 out of 5 average rating, 304 reviews
Guest favourite
Home in Grand Cayman
Cayman Sands by Grand Cayman Villas
5 bedrooms, 8 beds, 5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Grand Cayman
The Grove Too - 1 Bedroom Apartment
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
4.95 out of 5 average rating, 65 reviews