
From the Caribbean to the Alps: Villas Worth a Look This Christmas
If a private villa has been on your mind for this Christmas, here's a curated shortlist spanning the Caribbean, Europe, and a few unexpected corners of the US. Each one offers something different, from clifftop infinity pools in Croatia to a deep-water dock in the Pacific Northwest, so there's a fit here whether you're picturing beach days, mountain views, or a slower countryside pace.
Please note that travel pricing is dynamic and subject to change. Contact me for more details.
Caribbean

Rockspray — Providenciales, Turks & Caicos
Set on a peninsula surrounded on three sides by the turquoise waters of Chalk Sound, a protected marine park with minimal boat traffic, so swimming, snorkeling, and kayaking right off the property feel like having the water to yourselves. Both king bedrooms open onto private balconies overlooking the water, and the primary bath has a shower you can open to the elements. Brazilian wood cabinetry, Palladian French doors, and a covered exterior terrace round out the interior, with two kayaks included for exploring the sound. Sapodilla Beach is a short walk away. Good to know: this property doesn't accept groups of guests under 21, and a 7-night minimum applies over the holidays.

Villa Enjoy — Terres Basses, St. Martin

Oceanfront Cliffside Villa at Cocoa Cove — New Westerhall Point, Grenada

Ballena Blue — St. John, U.S. Virgin Islands
Panoramic views of Hart Bay and out to St. Croix, with a brand-new pool and a wraparound deck built for sunset watching, sunbathing, and al fresco dining. Vaulted ceilings and whitewashed interiors keep the great room bright, with a Sonos system and washer/dryer included. Each of the three bedrooms has its own en-suite bathroom. Close to Cruz Bay for dining and a short drive to Trunk Bay and Cinnamon Bay, two of the island's most renowned beaches. Good to know: no children between 8 months and 8 years are permitted, and bookings here are non-refundable.
Europe

Villa Vicka — Brela, Makarska Riviera, Croatia
5 bedrooms, 6 baths, sleeps 10.
Ten meters from a pebble beach on the Adriatic, with a heated infinity pool (complete with massage jets and Roman steps), a private gym, and sweeping sunset views over the bay. All five bedrooms are en suite, and the ground floor's glass walls flood the living and dining areas with natural light. A large private terrace has sunbeds, an outdoor dining table, and a grill for al fresco meals. A genuine standout if you're looking for the off-the-beaten-path European coastline rather than the usual Mediterranean hotspots. Note the 7-night minimum stay.

Rica — Montemagno, Tuscany, Italy
5 bedrooms, 5 baths, sleeps 10.
A restored 200-year-old farmhouse in the Tuscan hills near Lucca, with a saltwater pool set among olive groves and vineyards, plus a private gym and fireplace-warmed living room for cooler December evenings. Every bedroom is en suite with air conditioning, satellite TV, and a minibar. Past guests consistently mention the owners going above and beyond, one described being welcomed with a full table of homemade Italian food and estate wine on arrival. A car is necessary given the rural setting, but Florence, Siena, and the Cinque Terre are all reachable within a couple of hours.

Villa Mar Azul — Praia de Salema, Algarve, Portugal
6 bedrooms, 6.5 baths, sleeps up to 16.
Perched on a clifftop with panoramic ocean views from nearly every room, a private infinity pool, and a self-contained lower-floor apartment for added privacy within the group. You'll arrive to a welcome basket of wine, beer, local olive oil, and seasonal fruit, with daily housekeeping included throughout the stay. An outdoor dining area with a portable Kamado Joe grill makes the most of the coastal views. One of the largest properties on this list, well suited to a bigger multigenerational group.

Villa Palmeras de Mallorca — Port Andratx, Mallorca, Spain
4 bedrooms, 5 baths, 10 guests.
Set within the exclusive gated community of Las Brisas above Port Andratx, with round-the-clock security and lush Mediterranean gardens framing a spectacular sea view. Port Andratx itself has a genuinely upscale marina, quality restaurants, and an 18-hole golf course nearby, plus easy access to boating, diving, and snorkeling. A strong pick if you want villa privacy with easy access to a real night out just down the hill.

Parfum de Lavande — Bonnieux, Provence, France
5 bedrooms across two connected houses (the Old House and the Garden House), sleeps 10.
A 200-year-old restored farmhouse with a private pool and tennis court, set among lavender fields with sweeping views over the Luberon Valley and Mount Ventoux. The two houses sit just meters apart across a central walled courtyard, giving your group some built-in separation while staying close together. Good internet access makes this a comfortable option even if you need to stay connected during the trip.
United States

Chuckanut Point Villa — Bellingham, Washington
3 bedrooms, 3.5 baths, sleeps 8.
A modern waterfront retreat on Puget Sound with a private deep-water dock, two kayaks and two stand-up paddleboards included, and floor-to-ceiling glass framing water views from nearly every room. The primary suite has a spa-style en-suite with a soaking tub, and the boathouse suite offers its own kitchenette for extra flexibility. A fire pit and multi-level outdoor living space, including dining for ten, make this a great fit for evenings gathered outside. A genuinely different vibe from the rest of the list, ideal if you're picturing a Pacific Northwest holiday that leans cozy and scenic rather than tropical.

Big Pine Chalet — Big Sky, Montana
3 bedrooms, 3 baths, sleeps 8.
Walking distance to Big Sky Town Center and about 15 minutes from Big Sky Resort's slopes, with a private hot tub, gas fireplace, and mountain views from nearly every window. The open-concept main level connects the kitchen, dining, and great room, with a picnic-style table seating up to 8 and a private deck with a gas grill. The pick if you're after a classic ski-week Christmas instead of a beach one.
Any of these catch your eye? I'd love to help you sort out the details, availability, exact pricing, and anything else you'd want to know before booking. Book a consult and let's find the right fit for your Christmas!
