No. I · The Ranked Eight
From best to eighth.
Sorted by what each pocket does for the holiday: flight time, late-November weather, a kitchen and table that handle a 14-person dinner, and villa depth at the family size.
No. I
Los Cabos villa, the Corridor.
Format: six- to eight-bedroom villa with pool, ocean view, and full staff on the Tourist Corridor. Weekly rate: $20,000 to $50,000. Flight: short from the US West and Texas, easy connections from the East.
Why it ranks first: Cabo is the most reliable warm-weather Thanksgiving for a US group. Late November runs warm and dry, the villa inventory at the six-bedroom size is the deepest on this list, and the staffed estates here cook the dinner well or hand the kitchen to a host who wants to. The Corridor between San Jose and Cabo San Lucas keeps the restaurants and the golf within a short drive.
What we would change: the Corridor villas vary in beach access, and the Pacific side has strong surf not safe for swimming. Confirm whether the beach is swimmable or the pool is the water, and book the staffed tier so the dinner is covered.
No. II
Scottsdale desert villa, North Scottsdale.
Format: five- to eight-bedroom desert estate with pool, casitas, and mountain views. Weekly rate: $12,000 to $30,000. Flight: short and direct from most of the US, no passport.
Why it ranks second: Scottsdale is the easiest domestic Thanksgiving, with warm dry late-November days, no international travel, and the best value on this list. The desert estates carry big kitchens, long tables, and separate casitas for the grandparents or the teenagers, and the golf and spa scene fills the days around the dinner. It suits a group that wants warmth without a passport.
What we would change: November evenings in the desert turn cold fast, so confirm the outdoor dining has heaters or move the dinner inside. The best North Scottsdale estates book early for the holiday week.
No. III
Turks and Caicos beachfront villa, Providenciales.
Format: six- to eight-bedroom beachfront villa with pool and full staff on Grace Bay or the quieter coves. Weekly rate: $25,000 to $60,000. Flight: direct from the US East in three to four hours.
Why it ranks third: Providenciales gives the beach Thanksgiving with a short flight from the East Coast and reliably warm late-November water. The villas here run large, staffed, and right on the sand, and the cook can handle the dinner while the group spends the days in the water. It is the easiest Caribbean option for an East Coast family.
What we would change: Grace Bay is the busy strip, so for privacy look to the quieter coves like Long Bay or the north shore. Confirm the kitchen can roast the turkey, since some beach villas are built for grilling, not roasting.
No. IV
Big Island estate, the Kohala Coast.
Format: five- to eight-bedroom estate with pool and ocean view on the Kohala or Kona coast. Weekly rate: $18,000 to $50,000. Flight: direct from the US West, longer from the East.
Why it ranks fourth: the Kohala Coast gives Hawaii’s most reliable late-November sun, on the dry leeward side of the Big Island, with large estates near the Mauna Kea and Mauna Lani resorts. The villas carry the kitchens and tables for the dinner, and the snorkeling and the volcano fill the days. It suits a West Coast group willing to fly five hours for the islands.
What we would change: the flight is long for an East Coast group, so this rewards a longer stay than the holiday week alone. Confirm the estate is on the dry Kohala side, not the wetter Hilo coast.
No. V
Naples villa, the Gulf Coast of Florida.
Format: five- to seven-bedroom waterfront or near-beach villa with pool. Weekly rate: $14,000 to $35,000. Flight: short and direct from the US East and Midwest.
Why it ranks fifth: Naples keeps a beach Thanksgiving domestic and easy, with warm late-November Gulf weather and a short flight from the East. The waterfront villas carry the kitchens and the docks, the beach is calm for the youngest, and the dining scene runs strong. It suits a group that wants the beach without leaving the country.
What we would change: late November can bring a cool front to the Gulf, dropping the water temperature, so the pool may beat the sea on the cooler days. Confirm the villa has a heated pool.
No. VI
Anguilla beachfront villa, the West End.
Format: four- to seven-bedroom beachfront villa with pool and full staff. Weekly rate: $25,000 to $60,000. Flight: via St Maarten, then a short ferry or charter.
Why it ranks sixth: Anguilla gives the calmest, most private beach Thanksgiving in the Caribbean, with wide quiet sands and a quietly serious dinner scene. The West End villas run large and staffed, the cook handles the holiday meal, and the beaches stay uncrowded even over the holiday week. It suits a group that prioritizes a private beach over a short transfer.
What we would change: the St Maarten connection adds a transfer at each end, so build in the buffer time. The rate runs at the top of this list, so it rewards a group splitting the cost across several families.
No. VII
Punta Mita resort villa, the Riviera Nayarit.
Format: five- to eight-bedroom villa with pool and beach-club access inside the gated Punta Mita resort. Weekly rate: $20,000 to $55,000. Flight: via Puerto Vallarta, then a 45-minute drive.
Why it ranks seventh: Punta Mita pairs a staffed beach villa with full resort amenities behind a gate, with the golf, the beach clubs, and the kids’ programs that keep a multi-generational group occupied. Late November is warm and dry on the Nayarit coast, and the villa cooks the dinner. It suits a group that wants resort services alongside the villa privacy.
What we would change: the resort-villa premium is real, and you pay for the gate and the amenities. For a group that will not use the beach clubs or the golf, a Corridor villa in Cabo costs less for the same warm-weather dinner.
No. VIII
Palm Springs desert estate, the Coachella Valley.
Format: four- to seven-bedroom mid-century or contemporary estate with pool. Weekly rate: $12,000 to $28,000. Flight: short from the US West, easy drive from Los Angeles.
Why it ranks eighth: Palm Springs is the easy West Coast desert Thanksgiving, a short hop or a two-hour drive from Los Angeles, with warm dry days and the best architecture on this list. The estates carry pools, big kitchens, and the space for a group, and the value is strong. It suits a West Coast group that wants warmth and a short trip.
What we would change: like Scottsdale, the desert evenings turn cold in late November, so plan the dinner around the heaters or move it inside. The valley is spread out, so confirm the estate is near the dining you want.