Luxury beach homes for winter in Maui, San Diego, and Kiawah

Luxury beach homes for winter on the coast

Cooler months are prime time to enjoy luxury beach homes in three standout destinations: Maui, San Diego and Kiawah Island. From cultural festivals to holiday celebrations and championship golf, winter calendars fill up fast. Pacaso co-ownership gives you a refined base to settle in, host with ease and be minutes from the venues you care about most.

Luxury beach homes near Maui winter festivals

Hula O Na Keiki Festival runs November 7–9, 2024
The Sentry is scheduled January 2–5, 2025 at Kapalua
Maui Invitational is traditionally held in late November

Maui’s winter season blends oceanfront calm with marquee events. In early November, the Hula O Na Keiki Festival celebrates young hula dancers with competitions, workshops and an artisan market. The PGA TOUR opens its calendar on the Plantation Course in Kapalua with The Sentry in early January. And late November typically brings the Maui Invitational college basketball tournament to Lahaina. Maui's prime shoreline real estate underscores the appeal of being close to the action. Keawakapu Beachfront Estate spans 7,244 square feet, while residences at Wailea Beach Villas often range from roughly 1,900 to over 3,000 square feet. Communities like Moana Estates in South Kihei place owners near beach parks and local amenities. On the island's northwest coast, Kapalua offers resort living steps from championship golf.

Gourmet kitchen and open living at Lani in Kapalua, an elegant setting near The Sentry at the Plantation Course and seasonal Maui events.

Lani sits within Kapalua Resort, placing owners close to tournament week and seasonal festivities. Ocean views, a private lanai and a bright, modern kitchen make pre- and post-event gatherings effortless.

San Diego winter by the beach

San Diego luxury homes position you steps from bayside lights and coastal celebrations. SeaWorld San Diego’s Christmas Celebration runs through early January, complete with a towering tree, dazzling displays and snowfall moments. Nearby, LEGOLAND California’s Elf Extravaganza adds fireworks, dance parties and festive shows on select dates.

Easy transitions from waterfront strolls to dinner on the patio
Rooftop or upper-level decks for sunset views and nightcaps
Open kitchens and great rooms for holiday hosting

To keep evenings social and relaxed after a full day at the parks, prioritize outdoor living, bay access and multiple decks.

Sunset Bay's patio terrace and fire pit create a refined setting to unwind after San Diego's holiday shows and waterfront festivities.

Sunset Bay puts owners steps from Mission Bay, with nearly 750 square feet of decks and a rooftop fire pit for post-festival evenings. It illustrates how San Diego luxury homes pair indoor comfort with exceptional outdoor space.

San Diego’s coastal path sets the tone for winter runs, surf checks and easy access to seasonal lights and shows.

Kiawah Island celebrations and coastal comfort

Kiawah Island’s holiday calendar pairs Lowcountry charm with festive energy. Seasonal happenings include a Jingle Bell Brunch Buffet on December 24, a Holiday Sporting Clays Tournament from December 26 to 30, and a New Year’s Eve Bash on December 31 at the River Course. Many cultural events also unfold nearby in Charleston, roughly a 40-minute drive, including the Charleston Wine and Food Festival, SEWE and the Charleston Jazz Festival.

Open floor plans that make hosting simple
Screened porches for sunset cocktails
Easy routes to downtown Charleston for concerts and festivals

For winter getaways to your luxury beach home, look for spacious gathering areas, pools for warm afternoons and quick access to Charleston's venues.

Charleston Blvd in Isle of Palms offers generous indoor-outdoor living and a pool, with quick access to Charleston's winter events.

Charleston Blvd in Isle of Palms checks those boxes, with multiple levels for hosting, a private pool and screened porches, plus easy access to Charleston's winter festival lineup and nearby beaches.

Kiawah’s wide beach and nearby venues offer a refined rhythm for winter walks, tee times and holiday dining.

Why co-ownership fits winter on the coast

Own the time you actually use during peak festival months
Enjoy beautifully designed homes ready for hosting
Stay near headline events without hopping between short stays
Benefit from a modern approach to owning a second home

Pacaso co-ownership aligns with how many owners use their beach homes in the winter.

Plan your winter retreat

Set your calendar around the experiences you want most, and let your home do the rest. Explore winter-ready Pacaso listings in Hawaiian Islands, San Diego and Kiawah Island to discover luxury beach homes that fit your style. Curious how co-ownership works? Start with What is co-ownership, compare models in Fractional ownership vs timeshare, or estimate your budget with the Second home calculator. That way, your next season near the water is centered on events, great company and a home that fits your life. For those considering high-end homes in San Diego, Pacaso provides a clear path to own near the coastal action.Note: This article was generated with the help of an AI agent and reviewed by our editorial team to ensure accuracy and clarity.