Bermuda Winter Rentals & Holiday Homes

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

• Ocean Front Studio, Kayak available - Swimming, bring own snorkle Euipment
• Lovely Garden Setting, Close to Sail GP Site, PGA Port Royal,2 min walk to Beach
• Las Brisas apartment with pool and walk to beach + EV chargers
• Stunning Views of Horseshoe Bay Beach. Enjoy the sounds of the lapping waves!
• New cottage with water views
• Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!
• CHARMING THREE BEDROOM COTTAGE AT MARLEY BEACH, WARICK
• Cottage Priv. Pool & Tennis Beach 5 min Central
• Cozy stand alone cottage with Bermuda Character
• Extraordinary Bermuda retreat w/large cave, panoramic pool and viewing deck.

The average cost for winter rentals in Bermuda is $746 per night. Ownerdirect has a wide list of great winter places to stay near Bermuda 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 Bermuda that allow you to bring your pet or dog:

• Oceanfront Dock of the Bay Retreat
• Location! Location! SPRING SALE, Cross Bay Private Estate, next to Horseshoe Bay
• The Oxford House
• Frognal Apartment

See all pet-friendly vacation rentals in Bermuda on Ownerdirect

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

As of 2026, the data from Ownerdirect shows that there are over 200 private swimming pools or indoor pools accommodations near Bermuda along with other great amenities.