Chairman's Collection

44 VILLAS

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Drakothea

Drakothea

Mykonos / Mykonos
Bedrooms
5
Sleeps
12
from $932+
per nightnightly

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.

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Villa Rosa

Villa Rosa

Jamaica / Montego Bay
Bedrooms
4
Sleeps
8
from $1,557+
per nightnightly

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

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Nona at Reunion Resort

Nona at Reunion Resort

Florida / Reunion
Bedrooms
9
Sleeps
22
from $1,955+
per nightnightly

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

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Tranquility at Reunion Resort

Tranquility at Reunion Resort

Florida / Reunion
Bedrooms
12
Sleeps
28
from $1,999+
per nightnightly

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

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Makana on the Beach

Makana on the Beach

Jamaica / Discovery Bay
Bedrooms
7
Sleeps
14
from $2,071+
per nightnightly

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

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

Sapphire Seas Beach Estate is awaiting your enjoyment.

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Canoe Cove on the Beach

Canoe Cove on the Beach

Jamaica / Ocho Rios
Bedrooms
7
Sleeps
14
from $2,682+
per nightnightly

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

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Wailea Sunset Estate
Bedrooms
4
Sleeps
8
from $2,700+
per nightnightly

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

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Celebrity Oceanfront Estate

Celebrity Oceanfront Estate

California / La Jolla
Bedrooms
7
Sleeps
16
from $2,800+
per nightnightly

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

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Poderosa

Poderosa

Tuscany / Val d’Orcia
Bedrooms
9
Sleeps
14
from $3,311+
per nightnightly

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

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Isolé Brand New

Isolé

Florida / Reunion
Bedrooms
15
Sleeps
30
from $2,995+
per nightnightly

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

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A La Mer

A La Mer

St. John / Great Cruz Bay
Bedrooms
9
Sleeps
22
from $5,280+
per nightnightly

The buzz throughout St. John and in the world of luxury villas is all about the impressive scale and the barefoot elegance of À La Mer!

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Hualalai Estate

Hualalai Estate

The Big Island / Hualalai
Bedrooms
5
Sleeps
10
from $5,390+
per nightnightly

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.

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Casa Majani

Casa Majani

Punta Mita / La Punta Estate
Bedrooms
6
Sleeps
14
from $6,000+
per nightnightly

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

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Hawksbill

Hawksbill

Turks and Caicos Islands / Grace Bay
Bedrooms
10
Sleeps
20
from $7,100+
per nightnightly

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

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Machiavelli

Machiavelli

Tuscany / Florence Area
Bedrooms
10
Sleeps
20
from $8,413+
per nightnightly

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.

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Ani Anguilla Full Estate Perfect for large groups!

Ani Anguilla Full Estate

Anguilla / Little Bay
Bedrooms
10
Sleeps
20
from $7,500+
per nightnightly

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.

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Casa Tres Soles 180-degree Ocean Views

Casa Tres Soles

Punta Mita / El Banco
Bedrooms
9
Sleeps
18
from $9,500+
per nightnightly

Our Exclusive Offers:
 Free 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.

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Lazy Lizard at Jumby Bay

Lazy Lizard at Jumby Bay

Antigua / Jumby Bay Resort
Bedrooms
6
Sleeps
12
from $14,500+
per nightnightly

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

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La Vida

La Vida

Punta Mita / El Banco
Bedrooms
8
Sleeps
20
from $20,000+
per nightnightly

Our Exclusive Offers:
 Free Night

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

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