Weston Winter Rentals & Holiday Homes

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

• Beautiful Onyx Luxury villa
• Marsh Mellow (4 bedroom)
• Aquilae: Luxury 5-bedroom villa with pool and stunning 180° sea view
• Villa Half Moon - Four Bedroom Villa, Sleeps 8
• Reeds Penthouse #12 - Amazing 3 Bedroom Villa on the cusp of Reeds Bay.
• Solaris Beach House Luxury apartment
• Secret Cove 1 is like an enchanting cabin in the woods, set amid rustling
• Secret Cove #4 is like an enchanting cabin in the woods, set amid rustling
• Located within the exclusive Royal Westmoreland Resort's, Breakaway is a beautiful apartment
• Superbe Condos vue sur la mer

The average cost for winter rentals in Weston is $1,379 per night. Beachbaycottages has a wide list of great winter places to stay near Weston 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 Weston that allow you to bring your pet or dog:

• Atelier House – Architectural Elegance with Panoramic West Coast Views, Barbados
• Villa with Incredible Ridge View and Pool - Marsh Mellow
• Luxury Modern Beachfront Villa - Onyx
• Tiny Home Retreat Near Beach- Marsh Mellow Cottage

See all pet-friendly vacation rentals in Weston on Beachbaycottages

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

As of 2026, the data from Beachbaycottages shows that there are over 35 private swimming pools or indoor pools accommodations near Weston along with other great amenities.