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.
Photo: Illustrative image of a timber-and-glass house among autumn trees; not a photograph of the destination.
Live inventory
Nightly rates in the Collection
Indicative nightly rates from our listed inventory, read each time this page loads. Final prices and dates are confirmed on the booking partner's site. Availability was last confirmed on 16 September 2026, so open dates are not shown.
TL;DR — the short version
In brief
A guide to renting private estates across the Americas: indicative rates for Aspen, Careyes, Harbour Island, Los Cabos, Jackson Hole and St Barths, peak-week pricing, staffing norms and the booking windows that matter.
How much does a luxury estate in Aspen cost per week?
Rates vary widely by property, season and party size; compare live partner rates for your dates.
Typical price band
Check property-specific partner rates
Indicative only. Our booking partners confirm live rates and availability for your exact dates.
At a glance
- 6 destinations
- Estates in Folio IV Source
- St Barths, Christmas–New Year
- Sharpest peak
- Los Cabos, year-round
- Longest season
Book a stay in Caribbean
Set your dates to see what the week costs — our villas first, then live rates with our booking partners for this destination.
Our villas in The Hamptons
East Hampton, New York
$18,000 / night
Water Mill, New York
$14,500 / night
Our villas in Aspen, Colorado
Starwood, Aspen, Colorado
$15,500 / night
Hotels and other rentals
Partner rates are indicative and confirmed at checkout. Some links are affiliate links.
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.
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 villas 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. Roughly November to April is high season; summer rates are often lower.
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 villas are larger.
St Barths
The sharpest calendar anywhere in the Collection. Rates can rise sharply between November and the week of New Year, when long minimum stays are common; compare live partner rates.
What it costs
The Christmas–New Year fortnight is a separate market in Aspen, Harbour Island and St Barths: minimum stays are often longer, deposit terms can be stricter, and the rate bears no relation to the rest of the calendar.
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 villas 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, as early as your dates are fixed.
- 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 these vary by town and county, so check the full total before booking.
- 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?
- Rates vary widely by property, season and party size; compare live partner rates for your dates.
- Why is St Barths so expensive at New Year?
- Inventory is fixed, demand is concentrated into two weeks, and many villas set long minimum stays. Rates over that fortnight are often well above November or April for the same villa; compare live partner rates.
- 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 villa 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. Partners confirm live pricing for your dates.