Caribbean Corporate Retreat Villas

You work hard, so you deserve a little time in paradise. Your next business trip or corporate retreat should be on a tropical island. Or how about something a little more special, like a private island. Reward those who work so hard for your company's success. Reward yourself!

Luxurious, private island with a full staff, six beaches, and every activity you could ask for. Calivigny Island - Just South of Woburn Bay, Greneda

Grenada

Beachfront | Pool | AC

from $120000/Nt
25 25
Details
Private island resort with rustic, eco-friendly design and every activity under the sun. Thatch Caye photo

Belize

Near Beach

from $9785/Nt
15 15
Details
Luxurious private estate with resort amenities, professional service, and 10 huge Master Suites. 10 BR rate available.
Has specials. Ani Villa Estate in The Dominican Republic has an amazing infinity edge pool with Caribbean views

Cabrera, Dominican Republic

Pool

from $9120/Nt
14 14
Details
Arrecife 23/24/25 Estate at Punta Cana Resort photo

Punta Cana, Dominican Republic

Pool

from $4390/Nt
13 13+
Details
This totally private island will make you feel like royalty. Has specials. Necker Island, BVI 2018 Helicopter view

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $62500/Nt
12 11
Details
Combine business with pleasure at Musha Cay at Copperfield Bay, where there are five houses to choose from and a host of sporting activities. 6, 7, 8, 9, 10 & 11 BR rates available. Musha Cay at Copperfield Bay photo

Musha Cay, Bahamas

Beachfront | Pool | AC

from $39000/Nt
12 13+
Details
Six acre estate with beachfront access to coral reefs, on-site sports courts, and two freshwater pools. 7, 8, 9, 10 & 11 BR rates available.
Has specials. Lounge by the pool at Golden Clouds

Ocho Rios, Jamaica

Pool

from $1571/Nt
12 12
Details
Platinum Coast villa with 11 bedrooms, a spacious layout, and sunset views. Has specials. Sanzaru photo

Barbados

Pool

from $11000/Nt
11 11
Details
This private, beachfront villa has a full staff and five-star amenities for everyone in your party. 9 BR rate available.
Has specials. The beautiful Cerulean Villa on Barnes Bay in Anguilla

Anguilla

Beachfront | Pool | AC

from $14286/Nt
11 9+
Details
2, 3, 4, 5, 6, 7 & 8 BR rates available. Enjoy relaxing by the pool and spectacular views of the Sir Francis Drake Channel beyond

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $6000/Nt
10 9
Details
Sophisticated, three-story home perfect for family vacation or getaway with friends. 5 BR rate available. The Beach House at Calivigny Island

Grenada

Beachfront | Pool | AC

from $40000/Nt
10 10
Details
Luxurious, expansive mansion in a tropical oasis. The amazing infinity edge pool at Casa de Camp #3607 overlooks the Chavon River and the ocean beyond

Casa de Campo, Dominican Republic

Pool

from $6500/Nt
10 10+
Details
A horseback ride on a semi-private beach is just one of the suprises at this 10 acre, nine cottage oasis in Jamaica Lazy Heart Villa is located just along the Playa Caleton Paquena

Cabrera, Dominican Republic

Near Beach | Pool

from $1500/Nt
10 9
Details
Huge luxury estate features two separate villas, a full staff, and incredible ocean views. 8 BR rate available.
Has specials. Ani Estate Anguilla - North and South

Anguilla

Pool

from $7500/Nt
10 10
Details
Large beachfront estate with two pools that's ideal for family and friends alike. 5, 6, 7, 8 & 9 BR rates available. Casa Sunshine photo

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

from $1214/Nt
10 10
Details
Pool area for Arrecife Villas

Punta Cana, Dominican Republic

Pool

from $2790/Nt
9 9
Details
Fully staffed, avant-garde villa with open-concept design and complimentary access to Eden Roc Beach. 5, 6, 7 & 8 BR rates available.
Has specials. Yarari Royale is a beautiful home located in Cap Cana

Cap Cana, Dominican Republic

Pool

from $2430/Nt
9 9+
Details
Chic and modern home with nine suites and tons of outdoor space. 5 BR rate available. The Overhang House at Calivigny Island

Grenada

Beachfront | Pool | AC

from $35000/Nt
9 9
Details
A former embassy, this sprawling property is set up for big groups. The villa has a full staff and a fantastically creative manager. Its also walkable to a beach which is hard to find in St Lucia. 5, 6, 7 & 8 BR rates available. Capri Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $850/Nt
9 9+
Details
Ultra private, beachfront estate! Has specials. Santosh a is located along a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $7000/Nt
9 9
Details
6 BR rate available. The luxurious patio and and infinity edge pool at Casa de Campo #3613

Casa de Campo, Dominican Republic

Pool

from $3500/Nt
8 8
Details
A resort style poo area at this villa in Casa de Campo

Casa de Campo, Dominican Republic

Pool

from $2900/Nt
8 8+
Details
6 BR rate available. Casa de Campo #3022 photo

Casa de Campo, Dominican Republic

Pool

from $2000/Nt
8 8
Details
Luxurious private villa with resort amenities, professional service, and a personal sandy beach area. 5 BR rate available.
Has specials. The swimming pool at the Larimar Villa overlooks the Caribbean

Cabrera, Dominican Republic

Pool

from $4720/Nt
8 8
Details
Over 20,000 square feet of enjoyment space. 2, 3, 4, 5, 6 & 7 BR rates available. Ultimacy Villa is located in Rose Hill in Island Harbor

Anguilla

Pool

from $1000/Nt
8 9+
Details
Darsena 20 Villa photo

Casa de Campo, Dominican Republic

Pool

from $2540/Nt
8 10
Details
Wedding-friendly resort villa with a swim-up bar and a bunk room. Casa de Suenos is located within the gated Los Suenos Resort community

Costa Rica

Pool

from $1800/Nt
7 7
Details
Big groups will love this waterfront villa. 5 BR rate available. Private pool deck at Vieux Caribe Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1210/Nt
7 7+
Details
Six bedroom oceanfront property with a protective coral reef 6 BR rate available.
Has specials. Twin Palms Villa - the namesake beautiful palm trees

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
7 4
Details
18-guest villa with oceanfront privacy, 75-foot pool, and space for everyone. 5 & 6 BR rates available.
Has specials. Aerial view of Villa Mora

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1600/Nt
7 7+
Details
Casa de Campo #2305 photo

Casa de Campo, Dominican Republic

Pool

from $3500/Nt
6 6
Details
Experience the ease of a stress-free vacation at Punta Cana Resort, where childcare, on-site activities, and white sand beach alleviate every burden. Yellow Bear Villa - Very large pool and outdoor areas

Punta Cana, Dominican Republic

Pool

from $1750/Nt
6 6+
Details
Large beachfront villa with wraparound ocean views and lots of room for decompressing! Expansive living area has endless views of the ocean

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2929/Nt
6 7
Details
Three intimate villas perfect for a family vacation or romantic getaway. The beach front at the Beach Bungalows on Calivigny Island

Grenada

Beachfront | AC

from $27000/Nt
6 6
Details
Stunning property dripping with luxury. 4 BR rate available.
Has specials. Enjoy amazing sunsets from the beach at the Amber Villa

Cabrera, Dominican Republic

Pool

from $4000/Nt
6 6
Details
Multiple couples and families can enjoy paradise at this golf course villa. The Harmon Estate Villa is located in the Eco Golf Community

Costa Rica

Pool

from $1500/Nt
6 6
Details
Modern beachside villa with sound system, expansive outdoor space, and a gourmet kitchen. C\'est La Vie Villa photo

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $4714/Nt
6 6
Details
Witenblauw Estate has every creature comfort, three pools, and beach access. Witenblauw Estate Villa photo

Pelican Key (Dutch side), St. Martin

Beachfront | Pool | AC

from $2071/Nt
6 6+
Details
Enjoy total tranquility in a main house and guest cottage set amongst the lush hillside. 2, 3 & 4 BR rates available. Darcini Villa is located in Fish Bay with a south facing view of rolling hills

Fish Bay, St. John

Pool

from $514/Nt
5 5+
Details
Three beaches on a private Preserve surrounded by the lush jungle. Langarra Estate photo

St. Thomas, USVI

Pool

from $1081/Nt
5 5+
Details
Private boat dock, beach, and panoramic ocean views at this fully air-conditioned villa. The Beach House photo

St. Thomas, USVI

Beachfront | AC

from $1300/Nt
5 4+
Details
This villa has five spacious suites with sea view terraces. Has specials. Sea Villa is situated facing the beach with amazing unobscured ocean views

Anguilla

Beachfront | Pool | AC

from $3300/Nt
5 5+
Details
Enjoy easy beach access and spacious bedrooms. Has specials. Lounge in luxury at Sand Villa on Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $3100/Nt
5 4+
Details
Beautifully and thoughtfully designed for year-round solitude and relaxation. 3 & 4 BR rates available. Beautiful Anguillan sunset from the back porch at Amarilla

Anguilla

Near Beach | Pool

from $2100/Nt
5 5+
Details
Unparalleled luxury and access to the only golf course on Anguilla. Has specials. Sky Villa is the most private of the Long Bay Villas located just off the beach

Anguilla

Near Beach | Pool

from $2900/Nt
5 4+
Details
Ultra-modern upscale Anguilla villa with glass walls that face the sea. Champagne Shores villa sits on a secluded beach near Pelican Bay

Anguilla

Near Beach | Pool

from $1700/Nt
5 5+
Details
Resort fun with easy beach access and ocean views Villa Arrecife 25 at Tortuga Bay photo

Punta Cana, Dominican Republic

Pool

from $1720/Nt
5 5
Details
Villa Corales 18 photo

Punta Cana, Dominican Republic

Beachfront | Pool | AC

from $4550/Nt
5 5+
Details
Marina 2 photo

Punta Cana, Dominican Republic

Near Beach

from $3290/Nt
5 5+
Details
Glamorous, spacious villa with water access, chic decor, and stunning views. 1, 2, 3 & 4 BR rates available.
Has specials. Pool and backyard facing Great Cruz Bay at Ardisia Villa

Great Cruz Bay, St. John

Pool

from $1500/Nt
5 5+
Details