What are the top rated Winter Rentals in Breakers?

There are a lot of options in Breakers. If you plan on staying in the Breakers area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Breakers: <a href="/property/gorgeous-detached-sandy-beachfront-villa-at-azure-breeze-villas/HA-321197797" class="class="static-page-link"">Gorgeous Detached Sandy Beachfront Villa at Azure Breeze Villas.</a> <a href="/property/azure-breeze-3-peaceful-pristine-3bd-3-bath-away-from-crowds-beachfront/HA-321665989" class="class="static-page-link"">Azure Breeze 3! Peaceful &amp; Pristine-3Bd, 3 BATH AWAY from crowds! Beachfront!</a> <a href="/property/you-ve-arrived-beachfront-3br-condo-w-pool-relax-north-side-near-rum-point/HA-321316446" class="class="static-page-link"">YOU&#39;VE Arrived! Beachfront 3BR condo w/Pool-Relax. North Side near Rum Point</a> <a href="/property/grand-cayman-luxury-2-bedroom-2-bathroom-condo-wonderful-sea-view-terrace/HA-611872500" class="class="static-page-link"">Grand Cayman - Luxury 2 bedroom &amp; 2 bathroom condo, wonderful sea view terrace</a> <a href="/property/kitocay-modern-beach-house-w-over-the-water-sun-deck-private-beach-lot/HA-1219970820" class="class="static-page-link"">KiToCay: Modern Beach House w/Over-the-Water Sun Deck &amp; Private Beach Lot</a> <a href="/property/casa-tortuga-private-beachfront-villa-with-pool-call-cayman-villas/HA-3211669424" class="class="static-page-link"">Casa Tortuga - private beachfront villa with pool - Call Cayman Villas!</a> <a href="/property/conched-out-beach-house-w-backyard-snorkeling-private-pool/HA-1213523541" class="class="static-page-link"">Conched Out: Beach House w/Backyard Snorkeling + Private Pool</a> <a href="/property/oceanfront-resort-villa-w-stunning-views-pool-spa-onsite-staff/HA-3213105075" class="class="static-page-link"">Oceanfront Resort Villa w/Stunning Views, Pool, Spa &amp; Onsite Staff</a> <a href="/property/4br-suite-at-black-urchin-boutique-resort/HA-3213104963" class="class="static-page-link"">4BR Suite at Black Urchin Boutique Resort</a> <a href="/property/kiboko/EP-102210439" class="class="static-page-link"">Kiboko</a>

How much does it cost to rent a place to stay near Breakers in the wintertime?

The average cost for winter rentals in Breakers is $2,073 per night. Execstays has a wide list of great winter places to stay near Breakers that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Breakers that allow pets?

Yes, here are the top cottage/chalet rentals in Breakers that allow you to bring your pet or dog: SKY Luxurious Tranquility on a Private Beach In A Protected Marine Environment Cayman Paradise Villa #1 Silver Reef Residencies Your Oceanside Retreat Awaits! See all <a href="/all/cayman-islands/breakers/pet-friendly-rentals" class="class=&#34;static-page-link&#34;">pet-friendly vacation rentals in Breakers</a> on Execstays

Do you have any winter rentals in Breakers that are suitable for families?

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

Are there winter accommodations in Breakers that have indoor swimming pools?

As of 2026, the data from Execstays shows that there are over 53 private swimming pools or indoor pools accommodations near Breakers along with other great amenities.