Chairman’s Collection villa rentals


Drakothea

Europe Villa

from $1188 /night
up to 12 guests

Drakothea

5 bedroom 6 bath Greece villa in Mykonos

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.

Hualalai Estate

United States Villa

rates on request
up to 10 guests

Hualalai Estate

5 bedroom 5.5 bath Hawaii villa in The Big Island

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.

Th 2

Midtown West Luxury Townhouse

United States Villa

rates on request
up to 10 guests

Midtown West Luxury Townhouse

5 bedroom 8 bath New York villa in New York City

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.

Dji As Smart Object 1 Ped 1

Cielo Mar

Central America Villa

from $4857 /night
up to 12 guests

Cielo Mar

6 bedroom 8 bath Costa Rica villa in Peninsula Papagayo

Cielo Mar is located in Peninsula Papagayo, a private luxury resort sanctuary that jots out into the Pacific Ocean in Costa Rica's north-west province of Guanacaste.

F A A B 1 Ab Cacc D 0 A 3 Eb

Lazy Lizard at Jumby Bay

Caribbean Villa

from $14500 /night
up to 12 guests

Lazy Lizard at Jumby Bay

6 bedroom 7 bath Antigua villa in Jumby Bay Island

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

Mg

Corales 28

Caribbean Villa

from $5250 /night
up to 16 guests

Corales 28

7 bedroom 7.5 bath Dominican Republic villa in Punta Cana

Villa Corales 28 is located in the Corales section of the exclusive gated community of Punta Cana Resort & Club, a 26-square mile paradise that is blessed with a temperate year-round climate, light rainfall, and soft breezes.

Poderosa

Europe Villa

from $3429 /night
up to 14 guests

Poderosa

7 bedroom 6 bath Italy villa in Tuscany

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

SkyRidgeRetreat

Sky Ridge Retreat

United States Villa

from $3150 /night
up to 21 guests

Sky Ridge Retreat

7 bedroom 8.5 bath Utah villa in Deer Valley

Sky Ridge Retreat hosts multiple patios with gorgeous views of Jordanelle reservoir and the slopes of Deer Valley.

Ccb D 5 C B 8 Af 7 Fb Dc 7 C

Celebrity Oceanfront Estate

United States Villa

from $2500 /night
up to 18 guests

Celebrity Oceanfront Estate

8 bedroom 7.5 bath California villa in San Diego

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

Lb 1

La Bergerie

Europe Villa

from $5460 /night
up to 16 guests

La Bergerie

8 bedroom 8 bath France villa in Cote D’Azur

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.

Tiberio

Europe Villa

from $3771 /night
up to 16 guests

Tiberio

8 bedroom 8 bath Italy villa in Umbria

Go through the entrance of this magnificent property, step on its brick-and-stone staircase and you know that your expectations will be exceeded.

Alamerpoolvolleyball 1

A La Mer

Caribbean Villa

from $5867 /night
up to 22 guests

A La Mer

9 bedroom 9.5 bath USVI villa in St. John

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!

Palapa And Pool Dusk

Casa Koko

Mexico Villa

from $5200 /night
up to 22 guests

Casa Koko

9 bedroom 8 bath Punta Mita villa in Punta Villela

Located amidst Punta Mita’s exclusive residential community and designed by renowned architect Juan Collignon & interior designer Karen Collignon.

Tres Soles Alta

Casa Tres Soles

Mexico Villa

from $9500 /night
up to 18 guests

Casa Tres Soles

9 bedroom 12 bath Punta Mita villa in El Banco

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.

Mas Des Poiriers C Oliver Fly Graphy

Le Mas des Poiriers

Europe Villa

from $12107 /night
up to 18 guests

Le Mas des Poiriers

9 bedroom 8 bath France villa in Provence

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

Nona at Reunion Resort

United States Villa

from $1784 /night
up to 22 guests

Nona at Reunion Resort

9 bedroom 12.5 bath Florida villa in Orlando

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

Villa And Pool House

Sweet Bocas

Central America Villa

rates on request
up to 18 guests

Sweet Bocas

9 bedroom 9 bath Panama villa in Bocas Del Toro

Sweet Bocas is an architecturally stunning, handcrafted villa that floats off the shore of its own private island in Panama’s Caribbean waters.

Ani Villas Anguilla Cg 1 Long

Ani Anguilla Full Estate

Caribbean Villa

from $5225 /night
up to 20 guests

Ani Anguilla Full Estate

10 bedroom 10.5 bath Anguilla villa in Little Bay

ÀNI Anguilla combines the exclusivity of a private villa with the service, staff, and amenities of a 5-star property.

Anivillas Thailand

Ani Thailand

Asia Villa

rates on request
up to 20 guests

Ani Thailand

10 bedroom 10 bath Thailand villa in Koh Yao Noi

The Ani Thailand estate is hidden away on a peaceful stretch of beach on the serene island of Koh Yao Noi.

Hawksbill

Caribbean Villa

from $10000 /night
up to 20 guests

Hawksbill

10 bedroom 10 bath Turks & Caicos villa in Providenciales

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

Res 6

Machiavelli

Europe Villa

from $8712 /night
up to 20 guests

Machiavelli

10 bedroom 10 bath Italy villa in Tuscany

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

Pliniana

Europe Villa

from $23047 /night
up to 20 guests

Pliniana

10 bedroom 9 bath Italy villa in The Lakes

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

Chateau Candolle 6

Chateau Candolle

Europe Villa

from $15056 /night
up to 22 guests

Chateau Candolle

11 bedroom 11 bath France villa in Provence

It was the property of the Counts of Provence, created a fiefdom by Henry III in 1576, and the greatest Provençal families owned it in turn.

Tranquility at Reunion Resort

United States Villa

from $1999 /night
up to 28 guests

Tranquility at Reunion Resort

12 bedroom 13.5 bath Florida villa in Orlando

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

Vicere

Europe Villa

from $5228 /night
up to 24 guests

Vicere

12 bedroom 12 bath Italy villa in Amalfi Coast

Villa Vicere is a luxury private villa set above the lively and chic town of Positano, rising at about 150 steps from street level.

Aerial 2 Copy

Ani Dominican Republic

Caribbean Villa

from $4925 /night
up to 28 guests

Ani Dominican Republic

14 bedroom 14 bath Dominican Republic villa in Puerto Plata

Designed by the Dominican Republic’s own Sarah Garcia, the architecture incorporates the finest in tropical design, contemporary finishes, and touches of Dominican heritage.

Villas 1

Isolé

United States Villa

from $3450 /night
up to 30 guests

Isolé

15 bedroom 15 bath Florida villa in Orlando

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

Necker Island Aerial

Necker Island Exclusive Use

Caribbean Villa

rates on request
up to 40 guests

Necker Island Exclusive Use

20 bedroom 20 bath BVI villa in Necker Island

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

Find Chairman’s Collection Villas


Travel Dates
Travel Dates


Villa Size
Villa Size
Price Range
Price Range (per night)

Prices represent the starting per-night rate for matched villas.

Amenities
Amenities
Collections
Collections
Regions
Regions

If none are checked then all regions are included.

Villa Destinations


Find Chairman’s Collection Villas