1. Cayman Islands
  2. Old Man Bay
  3. Holiday Homes

47+ Old Man Bay Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Old Man Bay

Discover more than 47 holiday rentals in Old Man Bay. PickleTrip™ holiday homes has everything you need to find a place to stay near Old Man Bay, .

Whether you are looking for luxury villas in Old Man Bay, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Old Man Bay with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Old Man Bay for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Old Man Bay with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Old Man Bay Holiday Rentals

There are many holiday rentals available in Old Man Bay; however, here are a few of the most popular holiday homes listed in Old Man Bay on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Old Man Bay to find one that works for you.
Yes, there are 47 self-catering family homes and holiday rentals in Old Man Bay.
There are more than 47 luxury holiday homes in or near Old Man Bay, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 47 pet friendly rentals that are available in Old Man Bay.