Where to go for the best winter beach getaways

Winter beach getaways with year-round appeal

Trade snow for salt air with winter beach getaways in Cabo, Kiawah Island, and San Diego. Each coastline offers a distinct rhythm in the cooler months, from warm Baja sunshine to quiet Atlantic sands and Southern California’s effortless energy. This is the season to reset your routine, lean into golf, coastal walks, whale watching or surf sessions, and enjoy long, unhurried evenings at your home by the water. If you find yourself returning each year for winter beach vacations, Pacaso co-ownership makes it easy to enjoy that lifestyle on your terms.

Cabo San Lucas pairs sunshine with outdoor adventure

Cabo’s winter is made for ocean days and desert views. Mornings can mean tee times, glassy sea paddles or a captain-led outing to spot migrating whales. Afternoons shift to art walks, farm-to-table dining and golden-hour strolls along swimmable coves. As a base, Casa Bella brings indoor and outdoor living together, with an expansive lounge, pool and spa that set the scene for easy winter evenings with friends.

Casa Bella in Los Cabos offers expansive indoor and outdoor living with a pool and spa, ideal for a winter retreat close to beaches and Baja adventures.

Set your winter rhythm in Cabo with simple, high-reward routines that make the most of daylight and warm evenings.

Start with a sunrise stretch and coffee on the terrace, then head out for a coastal hike or stand-up paddle session.
Break for a long lunch and a gallery stroll, then book a tee time for late afternoon.
End the day with a private chef tasting or seaside dinner, followed by stargazing by the pool.

Cabo beachfront lounge scene that captures the relaxed pace of winter days by the water.

Cabo’s loungy, poolside afternoons are part of the appeal of a winter escape, especially when your home opens directly to the sun and sea air.

Kiawah Island balances quiet beaches and championship golf

Winter on Kiawah means wide, uncrowded beaches and prime tee times. The island is home to five championship golf courses, including the famed Ocean Course, so you can play at a high level and still have time for bike paths through maritime forest and sunset walks on firm sand. For an oceanfront vantage point, Shipwatch offers a bright sunroom and sweeping Atlantic views that are especially calming in the cooler months.

Shipwatch on Kiawah Island features a sunroom and Atlantic views, an ideal setting for quiet winter mornings and ocean-watching days.

Here, the pace invites longer outings and unhurried evenings.

Walk or bike the shoreline when the beach is quieter and the air is crisp.
Schedule golf in the late morning, then wind down with oysters and a coastal drive.
Spot wildlife in the marshlands before dinner, then read by the fire back at your home.

Kiawah’s palm-lined waterways reflect the calm, nature-forward pace of winter on the island.

The island’s natural setting shines in winter, with light traffic, easy dining and generous tee time options that support relaxed winter beach getaways.

San Diego brings mild days and coastal energy

San Diego’s winter is made for outdoor living. Surf breaks in La Jolla and Encinitas roll all season, Torrey Pines offers scenic cliffside hikes and the dining scene hums without peak-season crunch. For oceanfront gatherings, Neptune Bluffs features a limestone-tiled terrace and fire pit that make cool coastal nights feel effortless, with glass doors that open the living spaces to Pacific views.

Neptune Bluffs in Encinitas showcases an oceanfront terrace and fire pit, ideal for San Diego’s mild winter evenings.

Shape your day around the coast and let evenings stretch out with friends and good wine.

Grab coffee and stroll the beach path at sunrise.
Book a surf lesson or explore tide pools at low tide.
Hike Torrey Pines, then dine by the water and close the night by the fire pit.

Why co-ownership fits winter beach getaways

If winter beach vacations are a core part of your year, Pacaso co-ownership gives you a curated, designer-furnished home in your favorite destination without the stress of full-time upkeep. You own an equity interest in a real home and enjoy streamlined use throughout the year, with professional care and local support so your time stays focused on the coast. New to the model of owning a second home together with others who love the same place Read more in What is co-ownership and see how your annual travel spend compares in Average vacation cost.

Plan your winter by the water

Ready to make this season your best on the coast Explore Pacaso homes in Los Cabos, Kiawah Island and San Diego, and use our Second home calculator to narrow your search. If you are comparing models of ownership, start with Pros and cons of fractional ownership and browse inspiration in Types of houses. Your next set of winter beach getaways can start now with a home that is ready the moment you arrive.Note: This article was generated with the help of an AI agent and reviewed by our editorial team to ensure accuracy and clarity.