The Billionaire
Villa Index 2026
Where the world’s wealthiest travellers are staying — and what they want when they get there.
The Index is maintained as a rolling series: the annual edition each December, with seasonal updates published between editions as demand shifts. The flagship ranking draws on Haute Retreats booking data; seasonal updates may add market-wide measurements, and each states its own method.
Thanksgiving week in the Caribbean: what can still be booked
The Holiday Update turns the Index from demand to supply. On 23 September 2026 we searched 2,664 Caribbean villa listings for the Saturday-to-Saturday Thanksgiving week, 21 to 28 November, and read the booking calendar of every villa that showed open. Eight weeks before arrival, fewer than one listing in four could still be booked. The island-by-island results are published in our guide to warm Thanksgiving destinations .
What the scan shows
The holiday premium is an island decision rather than a market rule. St Barts, Jamaica, the Cayman Islands and Anguilla price Thanksgiving as high season; Barbados, St Martin, the British Virgin Islands, St Lucia and Grenada still sell the week at their lowest published rates, because winter rates there begin in December. Across all 325 rate tables, 31% ask for seven nights or more.
And one villa in seven that looked open on screen needed a person to confirm it: 39 calendars showed no bookings at all, 18 villas had no live calendar, 3 were open in one system and taken in another, and 5 carried a minimum stay, a mid-week rate change or a missing rate that changed the answer.
“Software can show you that a villa is open. Only a call to the house can promise it, and one villa in seven still needs that call.”
Method: dated availability searches for Saturday 21 to Saturday 28 November 2026 across the Caribbean inventory of two major villa-rental platforms (2,664 listings), followed by a read of each open villa’s own booking calendar for the nights of 21 to 27 November. Villas listed more than once are counted once; Costa Rica is excluded. Uplift and minimum-stay figures come from the 325 published rate tables covering the week, comparing the Thanksgiving-week nightly rate with the same villa’s lowest published nightly rate. The Holiday Update measures the market, not only the Haute Retreats collection, and availability changes daily. The festive-weeks update for Christmas and New Year 2026–27 follows in October.
Top 10 ultra-luxury villa destinations for 2026
Ranked by booking interest, average nightly rates, proportion of fully staffed estates and independent market data. Based on Haute Retreats’ proprietary inquiry and booking data, cross-referenced with Knight Frank Wealth Report 2026, Savills Spotlight on Wealth Trends, and villa rental market reports from leading operators. Original report published December 2025.
#1 globally in the Haute Retreats Billionaire Villa Index. The benchmark for fully staffed estate travel — wine estates, hilltop villas and historic farmhouses in Val d’Orcia and Chianti. Tuscany holds the deepest inventory of fully staffed estates in the Index: luxury villas average around €21,000 a week , while the top tier — estates such as I Busini, Podere Tesoro and Rinascimento — averages €75,000 a week . Milestone celebrations, weddings and long multi-generational stays dominate. UHNW families book 6–8 months ahead for peak weeks.
#2 globally. Grace Bay beachfront estates, Leeward canal villas and — the defining ultra-luxury asset — Ambergris Cay , the all-inclusive private island reached by private flight. No day visitors, fully staffed, complete seclusion. Peak nightly rates reach $30,000–$50,000+. UHNW families secure festive weeks 6–8 months in advance.
#3 globally, and the highest weekly average in Italy at €42,000 . Historic palazzi, private piers and lakefront estates with Alpine backdrops. Villa Balbiano — interior by Jacques Garcia, seen in House of Gucci and used as a filming location for The Devil Wears Prada 2 — is the defining property in the Haute Retreats collection and the most expensive single villa in the Index at €30,000 a night fully staffed . North American buyers competing for private mooring access. UHNW families book 6–8 months ahead.
#4 globally. Clifftop terraces, private sea access, Positano and Ravello estates with dramatic coastal views. Chef-led gastronomy stays with private boat transfers dominate the Haute Retreats booking profile here, with in-residence chefs designing menus around the local fishermen’s catch and regional produce.
#5 globally. Punta Cana, Casa de Campo and the north coast — home to ÀNI Private Resorts. Multi-villa compounds accommodating 20–40 guests as a single “private resort” dominate the Haute Retreats booking profile. Annual family reunions and festive season escapes are the defining use case.
#6 globally. Desert-meets-ocean estates at Cabo San Lucas and San José del Cabo. Strong UHNW “workation” demand: Haute Retreats clients configuring villas with private offices, high-speed connectivity and media rooms — then hosting chef’s table dinners for partners the same evening.
#7 globally. The quintessential quiet-luxury Caribbean island. No building on St Barts may exceed the height of a palm tree by law — there are no large resorts, making private villa rental the only ultra-luxury option on the island. Grand Cul de Sac and Gouverneur are the most sought-after addresses in the Haute Retreats collection.
#8 globally. Infinity pools with Aegean views, whitewashed estates above Ornos and Aleomandra. Summer demand from May to October consistently outstrips supply at the top tier of the market. The Haute Retreats Mykonos collection, part of our wider selection of luxury villas in Greece , is a destination-first selection for guests who want design, gastronomy and privacy in equal measure.
#9 globally. Jungle-fringed villas with on-site wellness teams, private chefs and surf guides. Guanacaste and the south Pacific coast lead UHNW adventure-wellness demand. “Quiet luxury” in nature — privacy, authenticity and the freedom to tailor every moment — is the defining profile of the Haute Retreats Costa Rica guest.
#10 globally. Ultra-private waterfront compounds on Star Island, Indian Creek and Palm Beach. Growing UHNW workation demand from tech and finance principals — particularly in Q1 — mirrors the Los Cabos profile. Complete privacy, chef and butler arranged for the stay, no shared lobbies or hotel corridors.
“Our clients are no longer asking, ‘Which five-star hotel has the best suite?’ They’re asking, ‘Which villa can I turn into my family’s private resort for a week or a month?’ The answer is a fully serviced estate with a chef, butler, wellness team and complete privacy — in destinations that still feel discreet, authentic and quietly luxurious.”
Destination demand index — relative scores 2026
Composite score based on booking interest, average nightly rates and share of fully staffed estates. Tuscany indexed at 100 as the 2026 #1. Source: Haute Retreats proprietary booking data, December 2025.
Index scores are relative, with Tuscany benchmarked at 100. Scores reflect composite demand across three weighted signals: booking interest (confirmed reservations and inquiries), average nightly rate for fully staffed estates, and the proportion of properties in each destination offering private chef, butler and daily housekeeping as standard. Data covers confirmed bookings and forward inquiries for 2024–2025 stays. Full methodology available on request: [email protected]
The Weekly Rate Index
What a fully staffed estate actually costs, by the week. The ranking above scores demand on a relative scale; this publishes the absolute figures behind it. Italy is the first market released, drawn from our Italian villas enquiry data; further destinations follow as each dataset is compiled.
Weekly averages for fully staffed estates, drawn from Haute Retreats enquiry and booking data for Summer 2027 stays, compiled August 2026. Rates vary by property, party size and date. All figures in the Top tier column are stated per week so the destinations remain comparable; Villa Balbiano is quoted at €30,000 a night, shown here at its seven-night equivalent. Lake Como carries the highest weekly average in Italy and Villa Balbiano is the most expensive single villa in the Index; Tuscany has the deepest staffed inventory. Full methodology and further markets available on request.
The Booking Lead Time Index
How far ahead the top of the market now commits. Across the Index’s leading destinations the booking window has moved from weeks to months, and in Italy the shift is not only earlier but longer — the same guests are holding villas for two and three weeks rather than one.
Lead times reflect Haute Retreats booking patterns across the Index destinations. They are behavioural observations rather than policy: shorter windows are sometimes available when a booking is released, which is worth asking about rather than assuming.
How ultra-luxury villa travel is changing in 2026
Billionaire workations become the new boardroom
Ultra-wealthy principals are turning board meetings, founder retreats and deal-making sessions into villa-based workations. Flagship villas in Los Cabos, Turks & Caicos, Miami and Lake Como are being configured with private offices, high-speed connectivity, media rooms and hotel-level catering — all within the complete privacy of a private estate.
“The modern family office doesn’t stop at the office door. We’re curating villas where principals can review deals in the morning, have lunch by the pool with their children and host a chef’s table dinner for partners that same evening.”
Celebration compounds & multi-generational gatherings
Multi-generational and celebration travel dominate at the very top of the market. Strong demand for multi-villa compounds accommodating 20–40 guests as a single “private resort.” These estates are being programmed like boutique properties — complete with kids’ clubs, wellness schedules, private concerts and in-villa events — but with a single family or invite-only guest list.
- Tuscan wine estates for milestone birthdays
- Punta Cana and the Dominican Republic north coast for annual family reunions
- Turks & Caicos and Costa Rica beachfront compounds for festive season escapes
Quiet-luxury coastlines & discreet destinations
Quiet luxury is replacing ostentation as the ultimate status symbol. UHNW guests want to disappear into nature and thoughtful design rather than be seen in a lobby. For 2026, three destinations share the characteristics billionaire travellers prize most: privacy, authenticity and the freedom to tailor every moment.
- Costa Rica — jungle-fringed villas with wellness teams, private chefs and surf guides
- Turks & Caicos — private-island escapes on Ambergris Cay and Parrot Cay, long empty stretches of sand
- Tuscany & Lake Como — historic villas reimagined with contemporary interiors, pools, spas and full staff
Chef-led villa living
Private chefs are no longer a nice-to-have — they are the centrepiece of the stay. Guests are requesting chef-led itineraries built around the destination: truffle hunts in Tuscany followed by in-villa degustation dinners; beach barbecues in Turks & Caicos; plant-forward tasting menus in Costa Rica after a day of wellness activities.
Fully staffed villas — with chef, butler and housekeeping included — are outperforming self-catered properties across the Haute Retreats portfolio. The villa is no longer just accommodation; it is the guest’s private restaurant, bar and club.
The rise of early booking — the best villas go first
For the most coveted properties in the top-ranked destinations, UHNW families are now typically securing peak-week stays six to eight months ahead of arrival. This applies especially to festive season and New Year’s weeks, school holiday periods, and wedding, anniversary and milestone celebration dates.
“The days of last-minute villa shopping for Christmas week on a top beach are effectively over at this level. Our clients treat their favourite villas the way they treat private jets or yachts — they reserve them early, return year after year, and expect a level of service that feels completely bespoke to their family and their values.”
How the Billionaire Villa Index is built
The Haute Retreats Billionaire Villa Index was published in December 2025 as part of the 2026 Ultra-Luxury Villa Trends Report. The Index ranks the most in-demand ultra-luxury villa destinations using three equally weighted signals, read alongside on-the-ground intelligence and drawn from Haute Retreats’ own verified booking and inquiry data across Europe, the Caribbean, Mexico and North America.
- Booking interest — Analysis of inquiries and confirmed bookings for 2024–2025 stays, forward-looking into 2026, across all Haute Retreats destinations
- Average nightly rates — Internal pricing trends for fully staffed, high-end properties catering to UHNW and HNW guests
- Share of fully staffed estates — The proportion of properties in each destination offering chef, butler and daily housekeeping as standard
- Qualitative intelligence — On-the-ground feedback from villa owners, local managers and on-site concierges in each destination
- Seasonal updates — Market-wide measurements published between editions, each with its own stated method; the September 2026 Holiday Update is a calendar-level scan of 2,664 Caribbean villa listings
The full report, including destination deep dives and sample itineraries, is available to media, travel advisors and concierge professionals upon request. Contact Enrico Crudo (Co-Founder) or Angelica Crudo at [email protected] . Tel: +1 888 279 6444 (toll-free US & Canada) · +1 305 432 1731 (Miami).
About the Billionaire Villa Index
What is the Billionaire Villa Index?
The Billionaire Villa Index is Haute Retreats’ annual ranking of the world’s most in-demand ultra-luxury villa destinations, published in December 2025 as part of the 2026 Ultra-Luxury Villa Trends Report. It ranks destinations by booking interest, average nightly rates and the proportion of fully staffed estates available in each location.
Which destination ranked #1 in the Billionaire Villa Index 2026?
Tuscany, Italy ranked #1 in the Haute Retreats Billionaire Villa Index for 2026, followed by Turks & Caicos at #2 and Lake Como at #3.
Why did Turks and Caicos rank #2 in the Billionaire Villa Index?
Turks and Caicos ranked #2 globally due to strong UHNW booking demand, particularly for Grace Bay beachfront estates and private island retreats on Ambergris Cay and Parrot Cay, combined with high average nightly rates and the near-universal availability of fully staffed villas with private chefs and butlers.
How far in advance should I book a luxury villa for Christmas or New Year?
According to the Billionaire Villa Index, UHNW families are now securing Christmas and New Year villas in top destinations six to eight months in advance. For Tuscany, Turks & Caicos, Lake Como and the Dominican Republic, peak festive weeks are typically fully reserved by mid-summer at the latest.
How many Caribbean villas are still available for Thanksgiving 2026?
Fewer than one in four of the 2,664 Caribbean villa listings checked on 23 September 2026 could still be booked for the Saturday-to-Saturday Thanksgiving week, 21 to 28 November. Counted once each, that is 449 villas across 17 islands. Availability changes daily.
Do Caribbean villas charge more for Thanksgiving week?
It depends on the island. The median villa on St Barts, Jamaica, the Cayman Islands and Anguilla prices Thanksgiving week 36–43% above its lowest published rate; on Barbados, St Martin, the British Virgin Islands, St Lucia and Grenada the median villa is still at its lowest published rate, because winter rates there begin in December.
What minimum stay do Caribbean villas ask for over Thanksgiving?
Two thirds of the rate tables accept five nights or fewer for the week, but 31% ask for seven nights or more — 93% on St Barts, and 85% or more on Anguilla and the British Virgin Islands.
How can I get the full 2026 Ultra-Luxury Villa Trends Report?
The full Haute Retreats 2026 Ultra-Luxury Villa Trends Report is available to media, travel advisors and concierge professionals upon request. Contact [email protected] or call +1 888 279 6444 (toll-free) or +1 305 432 1731 (Miami).
Request the full 2026 report
The complete Haute Retreats 2026 Ultra-Luxury Villa Trends Report — including destination deep dives, sample UHNW itineraries and supporting data — is available to journalists, travel editors, travel advisors and concierge professionals on request. The Holiday Update data is available under the same terms.
Enrico Crudo
— Co-Founder
[email protected]
+1 305 432 1731
Angelica Crudo
— Communications
[email protected]
Published 5 December 2025 via PRNewswire-PRWeb
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Luxury Travel Magazine, June 2026
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