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:

• Gorgeous Detached Sandy Beachfront Villa at Azure Breeze Villas.
• Azure Breeze 3! Peaceful & Pristine-3Bd, 3 BATH AWAY from crowds! Beachfront!
• Award Winning Sun Serenity Villa in Private Cayman Kai
• Romantic Walks on the Beach, Gorgeous Sunsets from Any Balcony.
• Tranquil Island vibe of the Caribbean with a healthy dose of posh
• The Meridian, Villa 11, Second floor, 3Bed 3Bath, Oceanfront, fully equipped.
• Barco A La Vista - Grand Cayman
• Casa Luna 14: Gated Resort South of 7Mile Beach w/Beach Cove, Communal Pool, Heated Spa + Gym
• Villa 17, Third floor, 3 bedroom, 3 bathroom, oceanfront, fully equipped.
• The Meridian - Villa 3, Oceanfront, Ground floor, 3 Bed, 3Bath, fully equipped.

The average cost for winter rentals in Grand Cayman is $2,528 per night. Luxurysicilyvilla 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:

• Oceans Edge SeaSide Estate is a stunning private villa right on the clifftop!
• Luxury villa with a private beach! Pool overlooking the ocean!
• Villa 3, Ground floor, 3 bedroom, 3 bathroom, oceanfront, fully equipped.
• Serenity Sands is perfect for friends travelling together or a 2 couples!

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

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 Luxurysicilyvilla shows that there are over 134 private swimming pools or indoor pools accommodations near Grand Cayman along with other great amenities.