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.

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.

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.

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.

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.

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.

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.