Guide IV — Folio IV — The Americas
Estates of the Americas: Aspen, Careyes, Harbour Island, Los Cabos, Jackson Hole and St Barths
Two ski markets, three coastlines and one island that reprices entirely over Christmas. What the six estates in Folio IV cost, and how their seasons interlock.
The six estates and their seasons
Aspen, Colorado
Two peaks, not one: Christmas through Presidents' Day for skiing, and July through the September aspen turn for the summer season. Contemporary estates on Red Mountain carry the highest rates in the American ski market.
Careyes, Jalisco
Cliffside casitas and castles above the Pacific, rented as whole properties with staff. The season runs November to April; the architecture, not the resort infrastructure, is the reason to go.
Harbour Island, Bahamas
Clapboard houses on the pink sand at Dunmore Town, small in scale and highly seasonal. December to May, with the smallest inventory of the six and the fastest sell-out over the holidays.
Los Cabos, Baja California Sur
The most flexible market in the folio: large modern estates with full staff, direct US lift, and genuine year-round availability. October to May is high season; the summer discount is real.
Jackson Hole, Wyoming
Ranch estates with serious winter skiing and an August park season that now rivals it. Rates are lower than Aspen for equivalent square footage, and the houses are larger.
St Barths
The sharpest calendar anywhere in the Collection. A villa can quadruple between November and the week of New Year, when a fourteen-night minimum is common.
What it costs
The Christmas–New Year fortnight is a separate market in Aspen, Harbour Island and St Barths: minimum stays extend to ten or fourteen nights, deposits are non-refundable earlier, and the rate bears no relation to the rest of the calendar.
| Destination | Season | Shoulder week | Peak week |
|---|---|---|---|
| Aspen | Ski + summer | USD 20,000 – 45,000 | USD 60,000 – 250,000 |
| Careyes | Nov – Apr | USD 12,000 – 30,000 | USD 35,000 – 90,000 |
| Harbour Island | Dec – May | USD 10,000 – 30,000 | USD 35,000 – 100,000 |
| Los Cabos | Year-round | USD 10,000 – 25,000 | USD 30,000 – 120,000 |
| Jackson Hole | Ski + summer | USD 12,000 – 35,000 | USD 40,000 – 150,000 |
| St Barths | Dec – Apr | USD 15,000 – 40,000 | USD 70,000 – 300,000 |
Staffing and the details that decide the week
Mexico and the Caribbean
Careyes, Los Cabos and St Barths typically include a housekeeper and, at the top of the market, a cook. Provisioning is at cost; a dedicated driver is extra and worth it in Careyes and Harbour Island.
The Rockies
Aspen and Jackson Hole estates are usually rented unstaffed with a concierge attached. Private chefs, ski valets and drivers are contracted separately and book out over holiday weeks well before the houses do.
Access
Aspen and Jackson Hole have weather-sensitive runways; St Barths requires a light-aircraft hop from St Maarten with a daylight cut-off; Harbour Island needs a ferry from North Eleuthera. None of these is a detail on arrival day.
Booking checklist
- Treat Christmas–New Year as its own booking exercise, twelve months out.
- Confirm minimum-stay and changeover-day rules before choosing flights.
- Ask whether the estate is staffed, concierge-supported or self-catered.
- For St Barths and Harbour Island, book the onward hop or ferry the same day as the villa.
- Confirm local occupancy taxes and cleaning fees — in the US they can add 12–18%.
- Check altitude and heat: Aspen and Jackson Hole in winter, Los Cabos and Careyes in high summer.
Frequently asked questions
- How much does a luxury estate in Aspen cost per week?
- Indicatively USD 20,000 to 45,000 per week in the shoulder season, rising to USD 60,000 to 250,000 over Christmas, New Year and Presidents' Day, before taxes, cleaning and separately contracted chef or ski staff.
- Why is St Barths so expensive at New Year?
- Inventory is fixed, demand is concentrated into two weeks, and most villas impose a ten- to fourteen-night minimum. Rates over that fortnight commonly run three to four times the November or April figure for the same house.
- Which destination in the Americas offers the best year-round availability?
- Los Cabos. It has direct US lift, a genuine year-round season and the deepest inventory of large staffed estates, with meaningful summer pricing between June and September.
- Are estates in Aspen and Jackson Hole staffed?
- Usually not in the base rate. They are rented with a concierge service, and chefs, drivers and ski valets are contracted separately — book them at the same time as the house for holiday weeks.
Editorial note & limitations
Rates are indicative planning figures assembled from prime-market research and connected partner inventory in August 2026, not quotations. Every estate in the Collection is priced live and carries a USD 500 nightly floor.