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We are delighted to share with our valued guests the brand-new “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. 

BROWSE THE CHAIRMAN’S COLLECTION

43 Villas
Sort Results
Drakothea

Drakothea

Mykonos / Mykonos

5
Bedrooms
Sleeps
12
from $931+
per 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.

Villa Rosa

Villa Rosa

Jamaica / Montego Bay

4
Bedrooms
Sleeps
8
from $1,557+
per night

Villa Rosa is a stunning, modern villa in Montego Bay's Spring Farm neighborhood.

Nona at Reunion Resort

Nona at Reunion Resort

Florida / Reunion

9
Bedrooms
Sleeps
22
from $1,955+
per night

Welcome to one of the most spectacular luxury mansions in Orlando.

Tranquility at Reunion Resort

Tranquility at Reunion Resort

Florida / Reunion

12
Bedrooms
Sleeps
28
from $1,999+
per night

Overlooking the stunning Jack Nicklaus golf course, this brand new 12 bedroom luxury villa at Reunion Resort sleeps up to 28 guests.

Makana on the Beach

Makana on the Beach

Jamaica / Discovery Bay

7
Bedrooms
Sleeps
14
from $2,071+
per night

Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay.

Sapphire Seas Beach Estate
4
Bedrooms
Sleeps
8
from $2,600+
per night

Sapphire Seas Beach Estate is awaiting your enjoyment.

Canoe Cove on the Beach

Canoe Cove on the Beach

Jamaica / Ocho Rios

7
Bedrooms
Sleeps
14
from $2,682+
per night

Experience this 7-bedroom contemporary beachfront villa on three private acres in Old Fort Bay!

Celebrity Oceanfront Estate

Celebrity Oceanfront Estate

California / La Jolla

7
Bedrooms
Sleeps
16
from $2,800+
per night

The 9,000 square foot Celebrity Oceanfront Estate is a stunning resort like home, with private pool, Jacuzzi and pickleball court.

Poderosa

Poderosa

Tuscany / Val d’Orcia

9
Bedrooms
Sleeps
14
from $3,308+
per night

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

Isolé Brand New

Isolé

Florida / Reunion

15
Bedrooms
Sleeps
30
from $2,995+
per night

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

Wailea Sunset Estate
4
Bedrooms
Sleeps
8
from $3,050+
per night

The Wailea Sunset Estate is a beautiful four-bedroom, newer, luxurious estate home situated nearby two of South Maui's finest sandy swimming beaches.

Hualalai Estate

Hualalai Estate

The Big Island / Hualalai

5
Bedrooms
Sleeps
10
from $5,390+
per night

Our Exclusive Offers:
 10% Off

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.

Casa Majani

Casa Majani

Punta Mita / La Punta Estate

6
Bedrooms
Sleeps
14
from $6,000+
per night

From world-renowned architects Manolo Mestre and Juan Collignon comes Casa Majani.

Machiavelli

Machiavelli

Tuscany / Florence Area

10
Bedrooms
Sleeps
20
from $8,407+
per night

Our Exclusive Offers:
 Free Night

Villa Machiavelli is a one-of-a-kind experience nestled in the legendary wine making “Chianti Classico” region, just outside of Florence.

Ani Anguilla Full Estate Perfect for large groups!

Ani Anguilla Full Estate

Anguilla / Little Bay

10
Bedrooms
Sleeps
20
from $7,500+
per night

Perched on the breathtaking cliffs overlooking Anguilla’s Little Bay. Ani Anguilla is the first of an international collection of luxury private resorts aimed at delivering remarkable vacation experiences.

Casa Tres Soles 180-degree Ocean Views

Casa Tres Soles

Punta Mita / El Banco

9
Bedrooms
Sleeps
18
from $9,500+
per night

Crowning a dramatic cliff and providing uninterrupted ocean views in all directions, Casa Tres Soles is one of the most beautiful homes in Punta Mita.

La Vida

La Vida

Punta Mita / El Banco

8
Bedrooms
Sleeps
20
from $10,000+
per night

La Vida is a private beachfront Estate in the quaint resort community of Punta Mita.

Sullivan Estate

Sullivan Estate

Oahu / Haleiwa

6
Bedrooms
Sleeps
12
from $12,300+
per night

The Sullivan Estate is a luxurious 6 bedroom estate located on the North Shore of Oahu, just 40 minutes from Honolulu's world-class shopping, dining and the excitement of Waikiki.

Lazy Lizard at Jumby Bay

Lazy Lizard at Jumby Bay

Antigua / Jumby Bay Resort

6
Bedrooms
Sleeps
12
from $14,500+
per night

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

Deerhaven Gardens Award Winning Property

Deerhaven Gardens

North Carolina / Asheville

6
Bedrooms
Sleeps
16
from $1,800+
per night

The estate, approximately 5 miles south of downtown Asheville, sits high upon the east facing mountain ridge overlooking the community of Deerhaven.