Grand Cayman Winter Rentals & Holiday Homes

There are a lot of options in Grand Cayman. If you plan on staying in the Grand Cayman area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Grand Cayman:

• Seafire Residence S303
• Black Urchin Boutique Resort
• Tranquil Island vibe of the Caribbean with a healthy dose of posh
• Kimpton Seafire Resort + Spa by IHG
• The Ritz-Carlton, Grand Cayman
• VIDA Cayman
• VIDA Cayman Luxury Boutique Eco Hotel
• Palm Heights
• Family Condo with bunk beds and ocean views at The Ritz-Carlton
• The Westin Grand Cayman Seven Mile Beach Resort & Spa

The average cost for winter rentals in Grand Cayman is $2,706 per night. Unpluggedweekend has a wide list of great winter places to stay near Grand Cayman that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Grand Cayman that allow you to bring your pet or dog:

• Astonishing Oceanfront Residence Located at The Ritz-Carlton, Grand Cayman
• The Ritz-Carlton, Grand Cayman
• Wyndham Reef Resort - All Inclusive
• Contemporary ground-floor beachside Residence located at The Ritz-Carlton

See all pet-friendly vacation rentals in Grand Cayman on Unpluggedweekend

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Grand Cayman to find what works for you.

As of 2026, the data from Unpluggedweekend shows that there are over 78 private swimming pools or indoor pools accommodations near Grand Cayman along with other great amenities.