Villa Collection Curated by Our Chairman

Chairman's Collection

Pliniana
The Lakes, Italy

Find Your Villa

Guests:

We are delighted to share with our valued guests the “Chairman’s Collection,” an expertly curated list of the finest villas worldwide.

This incredible portfolio of world-class escapes exceeds an impressive selection criterion including, but not limited to:

  • Premier locations
  • Superior architecture
  • Pinnacle of privacy and exclusivity 
  • Exquisite design both indoors and out

Explore the Chairman’s Collection and discover the true art of premier luxury villa vacations. 

Featured Villas

Exclusive Offers
Guests 10 Bedrooms 10 Bathrooms

Machiavelli

Tuscany, Italy
from  $8,930.00 /night
Exclusive Offers
Guests 9 Bedrooms 12.5 Bathrooms

Nona at Reunion Resort

Orlando, Florida
from  $1,955.00 /night

More Villas

Exclusive Offers
12 Guests 5 Bedrooms 6 Bathrooms

Drakothea

Greece / Mykonos
from $1,190.00 /night
Exclusive Offers
20 Guests 10 Bedrooms 10 Bathrooms

Hawksbill

Turks & Caicos / Providenciales
from $10,000.00 /night
Exclusive Offers
10 Guests 5 Bedrooms 5.5 Bathrooms

Hualalai Estate

Hawaii / The Big Island
from $5,390.00 /night
Exclusive Offers
30 Guests 15 Bedrooms 15 Bathrooms

Isolé

Florida / Orlando
from $3,450.00 /night
Exclusive Offers
16 Guests 8 Bedrooms 8 Bathrooms

La Bergerie

France / Cote D'Azur
from $5,315.00 /night
Exclusive Offers
18 Guests 9 Bedrooms 9 Bathrooms

La Dolce Vita

Turks & Caicos / Providenciales
from $17,000.00 /night
Exclusive Offers
12 Guests 6 Bedrooms 7 Bathrooms

Lazy Lizard at Jumby Bay

Antigua / Long Island
from $14,500.00 /night
Exclusive Offers
18 Guests 9 Bedrooms 8 Bathrooms

Le Mas des Poiriers

France / Provence
from $12,107.00 /night
Exclusive Offers
10 Guests 5 Bedrooms 8 Bathrooms

Midtown West Luxury Townhouse

New York / New York City
from $16,320.00 /night
Exclusive Offers
40 Guests 20 Bedrooms 20 Bathrooms

Necker Island Exclusive Use

British Virgin Islands / Necker Island
from $105,000.00 /night
Exclusive Offers
20 Guests 10 Bedrooms 9 Bathrooms

Pliniana

Italy / The Lakes
from $23,624.00 /night
Exclusive Offers
14 Guests 7 Bedrooms 6 Bathrooms

Poderosa

Italy / Tuscany
from $3,515.00 /night
12 Guests 5 Bedrooms 6 Bathrooms

Drakothea

Greece / Mykonos
from $1,190.00 /night

Drakothea is a stunningly beautiful property and offers an extraordinary setting for a dream vacation. The distinctive combination of breathtaking views, artistic elements, modern amenities, privacy, luxury and comfort make this villa an exceptional vacation spot.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
20 Guests 10 Bedrooms 10 Bathrooms

Hawksbill

Turks & Caicos / Providenciales
from $10,000.00 /night

Hawksbill Villa is a 10-bedroom, Caribbean estate home within a number of separate buildings throughout the 5+ acre site.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
10 Guests 5 Bedrooms 5.5 Bathrooms

Hualalai Estate

Hawaii / The Big Island
from $5,390.00 /night

This magnificent island-inspired, custom home features over 6,300 square feet of elegant living space with four bedrooms, each complete with separate garden outdoor shower lanais as well as a fifth bedroom in an intimate guest house.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
30 Guests 15 Bedrooms 15 Bathrooms

Isolé

Florida / Orlando
from $3,450.00 /night

Brand new, five star service in the seclusion of your own private luxury destination. Isolé is the newest and largest villa in Reunion.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
16 Guests 8 Bedrooms 8 Bathrooms

La Bergerie

France / Cote D'Azur
from $5,315.00 /night

Perfectly positioned close to both Provence and the Cote d’Azur in the South of France, this incredible villa, with its stunning interior is set in beautiful surroundings and offers a calming blend of classic furnishings with contemporary features, flooded with natural light.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
18 Guests 9 Bedrooms 9 Bathrooms

La Dolce Vita

Turks & Caicos / Providenciales
from $17,000.00 /night

The crown gem of Grace Bay Resorts’ Private Villa Collection, the opulent La Dolce Vita villa sits on the shores of Providenciales’ Long Bay Beach with 9 bedrooms and expansive living space totaling more than 12,300 square feet.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
12 Guests 6 Bedrooms 7 Bathrooms

Lazy Lizard at Jumby Bay

Antigua / Long Island
from $14,500.00 /night

This exceptional and very private beachfront estate offers a luxurious fusion of Caribbean and Asian architecture.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
18 Guests 9 Bedrooms 8 Bathrooms

Le Mas des Poiriers

France / Provence
from $12,107.00 /night

Le Mas des Poiriers is an 18th century farm house in Provence, located near the Medieval city of Avignon on Isle de la Motte.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
10 Guests 5 Bedrooms 8 Bathrooms

Midtown West Luxury Townhouse

New York / New York City
from $16,320.00 /night

The Midtown West Luxury Townhouse is an incomparable showplace residence in Hells Kitchen, a rarely available, custom-built 25′ single-family townhouse set on a large 100-foot-deep lot.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
40 Guests 20 Bedrooms 20 Bathrooms

Necker Island Exclusive Use

British Virgin Islands / Necker Island
from $105,000.00 /night

Welcome! You’ve just arrived at Necker Island, Sir Richard Branson’s private island paradise.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
20 Guests 10 Bedrooms 9 Bathrooms

Pliniana

Italy / The Lakes
from $23,624.00 /night

Lake Como is considered a chic romantic paradise and is renown for its picturesque iconic sceneries.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars
14 Guests 7 Bedrooms 6 Bathrooms

Poderosa

Italy / Tuscany
from $3,515.00 /night

Set atop a hill, this elegant contemporary property dominates the surroundings and offers dramatic panoramas of the rolling Tuscan Hills.

Our Exclusive Offers:
  • Earn 3 miles per $1 spent plus get up to $4,000 in Destination Dollars