Our villas in 

Caribbean

Find your next adventure

What else can we say about the Caribbean that you can’t get from our stunning villa pictures? Search Sheldon James’ collection of luxury villas in the Caribbean and start dreaming. 

$2,858 - $5,715/nt
Amanoka, Discovery Bay, Jamaica,
14 Guests • 7 Bedrooms • 8 Bathrooms
$2,858 - $6,000/nt
Fortlands Point, Discovery Bay, Jamaica,
18 Guests • 9 Bedrooms • 9 Bathrooms
$11,000 - $39,000/nt
Sole e Mare, Turks and Caicos, Grace Bay,
20 Guests • 10 Bedrooms • 10.5 Bathrooms
$1,895 - $4,695/nt
Villa Mora, Grand Cayman, Cayman Kai,
18 Guests • 7 Bedrooms • 7.5 Bathrooms
$2,950 - $8,450/nt
SunRays, Grand Cayman, Cayman Kai,
22 Guests • 8 Bedrooms • 8.5 Bathrooms
$2,950 - $7,948/nt
Kaia Kamina, Grand Cayman, Cayman Kai,
18 Guests • 7 Bedrooms • 9 Bathrooms

The islands of the Caribbean can’t be painted with one brush, but common threads include warm, white sand and cool blue water, green hills and tropical rainbow-colored drinks, sunny smiles and relaxed flip-flop vibes. Tell us what you’re looking for and we’ll find the perfect villa for your next holiday.

$3,450 - $9,450/nt
Rip Kai, Rum Point, Grand Cayman,
24 Guests • 9 Bedrooms • 10.5 Bathrooms
$4,290 - $6,430/nt
Marina 1, Dominican Republic, Punta Cana,
14 Guests • 5 Bedrooms • 5.5 Bathrooms
$2,790 - $7,500/nt
Arrecife 9 BR (24 and 25), Dominican Republic, Punta Cana,
20 Guests • 9 Bedrooms • 9 Bathrooms
$714 - $1,929/nt
Bamboo, St. Martin, Terres Basses,
4 Guests • 2 Bedrooms • 2.5 Bathrooms
$786 - $2,357/nt
Lotus, St. Martin, Terres Basses,
6 Guests • 3 Bedrooms • 3.5 Bathrooms
$1,525 - $5,500/nt
Infinity Blue, St. Martin, Baie Rouge, Terres Basses,
12 Guests • 6 Bedrooms • 6 Bathrooms
$1,215 - $4,500/nt
Villa Numa, St. Martin, Indigo Bay,
12 Guests • 6 Bedrooms • 6 Bathrooms
$3,000 - $10,000/nt
Ocean Breeze, Turks and Caicos, Chalk Sound,
12 Guests • 5 Bedrooms • 5 Bathrooms
$4,500 - $16,000/nt
Villa Bash, Turks and Caicos, Leeward,
12 Guests • 6 Bedrooms • 6 Bathrooms
$1,860 - $5,000/nt
Villa Angelique, Dominican Republic, Punta Cana,
14 Guests • 6 Bedrooms • 7 Bathrooms
$3,400 - $5,430/nt
Marina 4, Dominican Republic, Punta Cana,
12 Guests • 5 Bedrooms • 6 Bathrooms
$2,000 - $5,000/nt
Corales 114, Dominican Republic, Punta Cana,
14 Guests • 6 Bedrooms • 7 Bathrooms
$1,457 - $3,257/nt
Carisa, St. Martin, Baie Rouge, Terres Basses,
4 Guests • 2 Bedrooms • 3 Bathrooms
$1,250 - $3,950/nt
The One at The St. James, Barbados, Paynes Bay,
8 Guests • 4 Bedrooms • 5 Bathrooms
Rates upon request
Beach Enclave Long Bay Beach House 2BR, Turks and Caicos, Long Bay,
4 Guests • 2 Bedrooms • 3 Bathrooms
$3,250 - $6,950/nt
Le Cabanon, Turks and Caicos, Chalk Sound,
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,400 - $2,070/nt
La Perla Classic, St. Martin, Baie Rouge, Terres Basses,
2 Guests • 1 Bedrooms • 2 Bathrooms
$4,714 - $12,143/nt
La Perla Palais, St. Martin, Baie Rouge, Terres Basses,
10 Guests • 5 Bedrooms • 5 Bathrooms
$7,000 - $15,714/nt
La Perla Estate, St. Martin, Baie Rouge, Terres Basses,
14 Guests • 7 Bedrooms • 7 Bathrooms
$1,400 - $2,070/nt
La Perla Bianca, St. Martin, Baie Rouge, Terres Basses,
2 Guests • 1 Bedrooms • 2 Bathrooms
$6,429 - $20,000/nt
Le Chateau Des Palmiers, St. Martin, Plum Bay, Terres Basses,
20 Guests • 10 Bedrooms • 11 Bathrooms
$2,000 - $8,572/nt
La Danse du Soleil, St. Barts, Toiny,
10 Guests • 5 Bedrooms • 5 Bathrooms
$2,200 - $7,000/nt
Below Deck, Turks and Caicos, Leeward,
10 Guests • 5 Bedrooms • 4 Bathrooms
$2,800 - $10,000/nt
Grace Too, Turks and Caicos, Grace Bay,
14 Guests • 6 Bedrooms • 5.5 Bathrooms
$5,500 - $15,000/nt
Villa Azzurra, Turks and Caicos, Grace Bay,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$4,285 - $13,571/nt
Only You, St. Barts, Petit Cul de Sac,
10 Guests • 5 Bedrooms • 5 Bathrooms
$8,500 - $19,000/nt
Emerald Bay, Turks and Caicos, Turtle Tail,
16 Guests • 7 Bedrooms • 7 Bathrooms
$16,000 - $35,000/nt
Laughing Waters, Barbados, Sandy Lane,
24 Guests • 12 Bedrooms • 12 Bathrooms
$13,750 - $25,000/nt
Sanzaru, Barbados, Sandy Lane,
22 Guests • 11 Bedrooms • 11.5 Bathrooms
$5,000 - $22,000/nt
Bachelor Hall, Barbados, St. James,
14 Guests • 7 Bedrooms • 7 Bathrooms
$1,700 - $3,875/nt
Tom Tom, Barbados, St. James,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
Rates upon request
Crystal Springs, Barbados, St. James, The Garden,
20 Guests • 10 Bedrooms • 10 Bathrooms
$3,150 - $12,000/nt
Footprints, Barbados, St. James,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$3,450 - $10,000/nt
Onyx, Weston, Barbados, St. James,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$12,000 - $28,000/nt
Greensleeves, Barbados, St. James,
20 Guests • 10 Bedrooms • 10 Bathrooms
$2,700 - $6,000/nt
Aqua Verde, Turks and Caicos, Grace Bay,
6 Guests • 3 Bedrooms • 3.5 Bathrooms
$4,860 - $18,572/nt
Mythique, St. Barts, Marigot,
12 Guests • 6 Bedrooms • 6 Bathrooms
$3,750 - $20,500/nt
Aama, Barbados, Sandy Lane,
14 Guests • 7 Bedrooms • 8 Bathrooms
$6,940 - $12,000/nt
Blue Oasis, Dominican Republic, Cap Cana,
16 Guests • 7 Bedrooms • 7.5 Bathrooms
$11,430 - $27,290/nt
The Beach House, Anguilla, Meads Bay,
16 Guests • 8 Bedrooms • 10.5 Bathrooms
$3,330 - $8,400/nt
Beach Enclave Long Bay Beach House 4BR, Turks and Caicos, Long Bay,
8 Guests • 4 Bedrooms • 4 Bathrooms
$13,800 - $41,000/nt
Hawksbill, Turks and Caicos, Grace Bay,
16 Guests • 8 Bedrooms • 8 Bathrooms
$1,600 - $5,500/nt
Turquoise Villa, Turks and Caicos, Grace Bay,
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$3,300 - $8,435/nt
Beach Enclave North Shore 5BR, Turks and Caicos, North Shore,
12 Guests • 5 Bedrooms • 6 Bathrooms
$5,027 - $12,128/nt
Beach Enclave North Shore Beachfront 5BR, Turks and Caicos, North Shore,
12 Guests • 5 Bedrooms • 6 Bathrooms
$3,307 - $6,142/nt
Promiseas, Jamaica, Ocho Rios,
16 Guests • 8 Bedrooms • 8 Bathrooms
$1,150 - $3,750/nt
Cayman Castle, Grand Cayman, East End,
12 Guests • 5 Bedrooms • 5.5 Bathrooms
$742 - $2,857/nt
Just in Paradise, St. Martin, Terres Basses,
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,700 - $3,285/nt
BougainVilla, Jamaica, Montego Bay,
12 Guests • 6 Bedrooms • 6 Bathrooms
$2,000 - $7,714/nt
Villa K, St. Barts, Anse des Cayes,
8 Guests • 4 Bedrooms • 4 Bathrooms
$2,750 - $8,150/nt
Wind Chime Villa, Turks and Caicos, Turtle Tail,
8 Guests • 4 Bedrooms • 5 Bathrooms
$7,000 - $21,286/nt
Casa del Mar, St. Barts, Petit Cul de Sac,
12 Guests • 6 Bedrooms • 6 Bathrooms
$2,900 - $14,575/nt
El Grand Azure, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 5 Bathrooms
$8,379 - $16,538/nt
Beach Enclave Grace Bay 6BR, Turks and Caicos, Grace Bay,
12 Guests • 6 Bedrooms • 7 Bathrooms
$7,166 - $13,671/nt
Beach Enclave Long Bay Beachfront 7BR, Turks and Caicos, Long Bay,
14 Guests • 7 Bedrooms • 8 Bathrooms
$7,056 - $13,451/nt
Beach Enclave Long Bay Beachfront 6BR, Turks and Caicos, Long Bay,
12 Guests • 6 Bedrooms • 6 Bathrooms
$7,023 - $12,128/nt
Beach Enclave Long Bay Beachfront 5 BR, Turks and Caicos, Long Bay,
10 Guests • 5 Bedrooms • 2 Bathrooms
$8,379 - $16,538/nt
Beach Enclave Grace Bay Beachfront 5BR, Turks and Caicos, Grace Bay,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$6,500 - $11,000/nt
Villa Ananda, Dominican Republic, Punta Cana,
16 Guests • 8 Bedrooms • 8.5 Bathrooms
$6,000 - $9,500/nt
Villa Ammonite, Dominican Republic, Punta Cana,
12 Guests • 6 Bedrooms • 8.5 Bathrooms
$5,280 - $8,000/nt
A La Mer, St. John, Great Cruz Bay,
14 Guests • 7 Bedrooms • 7 Bathrooms
$3,000 - $10,000/nt
Solenborg Estate, St. John, Denis Bay,
14 Guests • 7 Bedrooms • 7 Bathrooms
$1,250 - $2,960/nt
Hacienda 96 at Las Hamacas, Dominican Republic, Punta Cana,
12 Guests • 6 Bedrooms • 6 Bathrooms
$2,500 - $5,000/nt
Chez Moi, Dominican Republic, Punta Cana,
14 Guests • 7 Bedrooms • 7.5 Bathrooms
$935 - $2,000/nt
Old Trees 7 – Bella Vista, Barbados, Paynes Bay,
6 Guests • 3 Bedrooms • 3.5 Bathrooms
$15,000 - $20,000/nt
Dream Pavilion, Turks and Caicos, Ambergris Cay,
14 Guests • 6 Bedrooms • 9 Bathrooms
$13,572 - $39,286/nt
Neo, St. Barts, Saint Jean,
12 Guests • 6 Bedrooms • 6 Bathrooms
$3,450 - $14,000/nt
Altamer – Blue Diamond, Anguilla, Shoal Bay West,
11 Guests • 5.5 Bedrooms • 7 Bathrooms
$4,550 - $6,430/nt
Los Corales 18, Dominican Republic, Punta Cana,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$814 - $2,286/nt
Grand Palms, St. Martin, Terres Basses,
6 Guests • 3 Bedrooms • 3.5 Bathrooms
Rates upon request
Tranquility, Turks and Caicos, Leeward,
22 Guests • 11 Bedrooms • 13 Bathrooms
$6,500 - $25,715/nt
La Plage, St. Barts, Lorient,
14 Guests • 7 Bedrooms • 7 Bathrooms
$2,600 - $15,715/nt
Mes Amis, St. Martin, Terres Basses,
28 Guests • 14 Bedrooms • 14 Bathrooms
$4,215 - $19,500/nt
Sandyline, St. Martin, Terres Basses,
14 Guests • 7 Bedrooms • 8 Bathrooms
$1,000 - $3,500/nt
Le Rocher, St. Martin, Terres Basses,
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$785 - $3,857/nt
Villa Les Palmiers Bleu, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 6 Bathrooms
$1,500 - $3,200/nt
Beach Cake, Turks and Caicos, Turtle Cove,
4 Guests • 2 Bedrooms • 2.5 Bathrooms
$950 - $1,950/nt
Tarasand, Grand Cayman, Cayman Kai,
8 Guests • 4 Bedrooms • 3 Bathrooms
$1,100 - $4,000/nt
Les Jalousies, Grand Cayman, Cayman Kai,
8 Guests • 3 Bedrooms • 4 Bathrooms
$540 - $1,100/nt
Sugar Kube, Turks and Caicos, Turtle Cove,
2 Guests • 1 Bedrooms • 1.5 Bathrooms
$1,500 - $3,400/nt
Beach Kandi, Turks and Caicos, Turtle Cove,
4 Guests • 2 Bedrooms • 2.5 Bathrooms
$1,700 - $3,800/nt
The Beach House at Hawksbill, Turks and Caicos, Grace Bay,
6 Guests • 3 Bedrooms • 3 Bathrooms
$3,300 - $8,300/nt
Saving Grace, Turks and Caicos, Grace Bay,
8 Guests • 5 Bedrooms • 3.5 Bathrooms
$1,500 - $3,000/nt
La Vie en Bleu, St. Martin, Baie Rouge, Terres Basses,
4 Guests • 2 Bedrooms • 2 Bathrooms
$2,143 - $5,714/nt
La Dacha, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$1,000 - $2,714/nt
Le Grand Bleu, St. Martin, Terres Basses,
10 Guests • 4 Bedrooms • 4.5 Bathrooms
$400 - $2,000/nt
Casa Capriolo, St. Martin, Terres Basses,
4 Guests • 2 Bedrooms • 2 Bathrooms
$7,200 - $21,000/nt
Blondel Cove, Turks and Caicos, Leeward,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$3,300 - $7,500/nt
Bristol Bliss, Turks and Caicos, Turtle Tail,
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$7,500 - $20,000/nt
Kiko, Barbados, Paynes Bay,
18 Guests • 9 Bedrooms • 9.5 Bathrooms
$1,357 - $4,214/nt
Turtle Nest, St. Martin, Long Bay, Terres Basses,
8 Guests • 4 Bedrooms • 4 Bathrooms
$1,600 - $3,850/nt
Cayuco 9, Dominican Republic, Cap Cana,
14 Guests • 6 Bedrooms • 6.5 Bathrooms
$1,286 - $3,857/nt
Blue Beach, St. Martin, Long Bay, Terres Basses,
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$979 - $2,071/nt
Encore, St. Martin, Terres Basses,
12 Guests • 6 Bedrooms • 7 Bathrooms
$2,357 - $8,572/nt
Amandara, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 6 Bathrooms
$2,000 - $6,429/nt
Avanti, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$3,171 - $10,100/nt
Casa de la Playa, St. Martin, Long Bay, Terres Basses,
12 Guests • 5 Bedrooms • 6 Bathrooms
$5,000 - $17,500/nt
L’Oasis, St. Martin, Baie Rouge, Terres Basses,
12 Guests • 6 Bedrooms • 7 Bathrooms
$1,572 - $4,714/nt
La Salamandre, St. Martin, Terres Basses,
12 Guests • 6 Bedrooms • 6 Bathrooms
$2,971 - $8,257/nt
Petite Plage 5, St. Martin, Grand Case,
12 Guests • 6 Bedrooms • 7 Bathrooms
$2,471 - $7,095/nt
Petite Plage 4, St. Martin, Grand Case,
10 Guests • 5 Bedrooms • 6 Bathrooms
$2,714 - $10,714/nt
Amancaya, St. Barts, Anse des Cayes,
16 Guests • 7 Bedrooms • 6 Bathrooms
$2,142 - $7,142/nt
Javacanou, St. Barts, Marigot,
6 Guests • 3 Bedrooms • 3 Bathrooms
$6,500 - $32,143/nt
Firefly, St. Barts, Anse des Cayes,
14 Guests • 7 Bedrooms • 7 Bathrooms
$3,571 - $15,714/nt
My Way, St. Barts, Colombier,
10 Guests • 5 Bedrooms • 5 Bathrooms
$3,857 - $13,571/nt
Loukoko, St. Barts, Lurin,
6 Guests • 3 Bedrooms • 3 Bathrooms
$2,857 - $15,714/nt
Legends B, St. Barts, Lurin,
10 Guests • 5 Bedrooms • 5 Bathrooms
$3,571 - $14,285/nt
Ixfalia, St. Barts, Saint Jean,
8 Guests • 4 Bedrooms • 4 Bathrooms
$900 - $3,571/nt
Iris, St. Barts, Grand Cul de Sac,
6 Guests • 3 Bedrooms • 3 Bathrooms
$857 - $3,857/nt
Casa Roc, St. Barts, Gustavia,
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,000 - $5,714/nt
Feyrouz, St. Barts, Vitet,
10 Guests • 5 Bedrooms • 5 Bathrooms
$1,714 - $5,714/nt
Dzir, St. Barts, Colombier,
6 Guests • 3 Bedrooms • 4 Bathrooms
$1,857 - $7,857/nt
Alhena, St. Barts, Lurin,
6 Guests • 3 Bedrooms • 3 Bathrooms
$2,000 - $9,285/nt
Coco, St. Barts, Lorient,
6 Guests • 3 Bedrooms • 3 Bathrooms
$2,500 - $13,571/nt
Belle Etoile, St. Barts, Vitet,
10 Guests • 5 Bedrooms • 5 Bathrooms
$7,142 - $18,571/nt
Axel Rocks, St. Barts, Gustavia,
8 Guests • 4 Bedrooms • 4 Bathrooms
$8,571 - $20,000/nt
Dunes, St. Barts, Petite Saline,
12 Guests • 6 Bedrooms • 6 Bathrooms
$1,500 - $3,650/nt
Olympus, Grand Cayman, Cayman Kai,
12 Guests • 4 Bedrooms • 5.5 Bathrooms
$1,000 - $3,500/nt
L’Ecume Des Jours, St. Martin, Plum Bay, Terres Basses,
8 Guests • 4 Bedrooms • 4 Bathrooms
$1,025 - $2,910/nt
Villa Emeraude, St. Martin, Indigo Bay,
8 Guests • 4 Bedrooms • 4 Bathrooms
$1,642 - $5,000/nt
Serena, St. Martin, Baie Rouge, Terres Basses,
12 Guests • 5 Bedrooms • 5 Bathrooms
$1,143 - $4,286/nt
Villa Truffle, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 5 Bathrooms
$3,100 - $10,000/nt
Sand Villa, Anguilla, Long bay,
12 Guests • 5 Bedrooms • 5 Bathrooms
$4,200 - $11,700/nt
Sky Villa, Anguilla, Long bay,
10 Guests • 5 Bedrooms • 4.5 Bathrooms
$3,300 - $11,000/nt
Sea Villa, Anguilla, Long bay,
11 Guests • 6 Bedrooms • 5.5 Bathrooms
$1,400 - $5,000/nt
Round Rock Estate, Anguilla, Pelican Bay,
12 Guests • 6 Bedrooms • 8.5 Bathrooms
$1,700 - $4,000/nt
Champagne Shores, Anguilla, Pelican Bay,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$1,850 - $7,399/nt
Bird of Paradise, Anguilla, Sandy Hill Bay,
10 Guests • 5 Bedrooms • 4.5 Bathrooms
$5,000 - $19,500/nt
Santosha, Anguilla, Long bay,
21 Guests • 9 Bedrooms • 13 Bathrooms
$1,075 - $2,715/nt
Dreamin Blue, St. Martin, Happy Bay,
8 Guests • 4 Bedrooms • 4 Bathrooms
Rates upon request
Cerulean, Anguilla, Barnes Bay,
22 Guests • 11 Bedrooms • 12 Bathrooms
$3,450 - $12,000/nt
Kandara, Anguilla, West End,
12 Guests • 6 Bedrooms • 8 Bathrooms
$6,000 - $22,000/nt
Cabuya, Turks and Caicos, Leeward,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$6,900 - $20,000/nt
Salacia, Turks and Caicos, Grace Bay,
12 Guests • 6 Bedrooms • 9 Bathrooms
$2,425 - $6,500/nt
Milestone, Turks and Caicos, Grace Bay,
8 Guests • 4 Bedrooms • 4 Bathrooms
$7,500 - $17,000/nt
Villa Bella Vita, Turks and Caicos, North Shore,
20 Guests • 9 Bedrooms • 10 Bathrooms
$6,500 - $20,000/nt
Vision Beach, Turks and Caicos, Grace Bay,
10 Guests • 5 Bedrooms • 7 Bathrooms
$4,200 - $15,000/nt
Silver Sands, Turks and Caicos, North Shore,
16 Guests • 8 Bedrooms • 7.5 Bathrooms
$4,150 - $11,950/nt
Paradis Sur Mer, Grand Cayman, Cayman Kai,
12 Guests • 6 Bedrooms • 10 Bathrooms
$15,000 - $25,000/nt
Sentosa, Turks and Caicos, Leeward,
16 Guests • 8 Bedrooms • 10 Bathrooms
$1,950 - $4,250/nt
Moon Kai, Grand Cayman, Cayman Kai,
14 Guests • 6 Bedrooms • 6 Bathrooms
$6,900 - $20,000/nt
Awa, Turks and Caicos, Grace Bay,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$19,200 - $41,000/nt
Hawksbill Estate, Turks and Caicos, Grace Bay,
22 Guests • 11 Bedrooms • 11 Bathrooms
$8,000 - $20,000/nt
Amazing Grace, Turks and Caicos, Grace Bay,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$8,670 - $12,000/nt
Villa Tartaruga, Dominican Republic, Punta Cana,
16 Guests • 8 Bedrooms • 8.5 Bathrooms
$2,200 - $7,150/nt
Big Chill, Turks and Caicos, Leeward,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$2,400 - $9,000/nt
Sandy Bottom, Turks and Caicos, South Shore,
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$1,700 - $5,000/nt
Villa Alinna, Turks and Caicos, Chalk Sound,
10 Guests • 5 Bedrooms • 6.5 Bathrooms
$4,450 - $11,950/nt
Coconut Walk, Grand Cayman, 7-Mile Beach,
18 Guests • 8 Bedrooms • 7.5 Bathrooms
$3,950 - $9,450/nt
Kempa Kai, Grand Cayman, Cayman Kai,
16 Guests • 7 Bedrooms • 6.5 Bathrooms
$2,950 - $5,850/nt
Fischers Reef, Grand Cayman, Cayman Kai,
20 Guests • 8 Bedrooms • 8.5 Bathrooms
$943 - $4,560/nt
Villa Mirabelle, St. Martin, Terres Basses,
8 Guests • 4 Bedrooms • 4 Bathrooms
$1,850 - $4,250/nt
Kaiku, Grand Cayman, Cayman Kai,
15 Guests • 7 Bedrooms • 6.5 Bathrooms
$2,800 - $4,860/nt
Villa Amalia, St. Martin, Guana Bay,
12 Guests • 6 Bedrooms • 6 Bathrooms
$4,714 - $12,143/nt
C’est La Vie, St. Martin, Plum Bay, Terres Basses,
12 Guests • 6 Bedrooms • 6 Bathrooms
$821 - $3,214/nt
Giselle, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 5 Bathrooms
$1,357 - $4,286/nt
Always, St. Martin, Terres Basses,
12 Guests • 6 Bedrooms • 7 Bathrooms
$1,429 - $6,429/nt
Fleur de Cactus, St. Barts, Lurin,
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,857 - $12,857/nt
Eclipse, St. Barts, Vitet,
12 Guests • 6 Bedrooms • 6 Bathrooms
$2,857 - $7,857/nt
Casa Pablo, St. Barts, Grand Cul de Sac,
8 Guests • 4 Bedrooms • 3 Bathrooms
$1,071 - $5,400/nt
Eden House, St. Barts, Marigot,
6 Guests • 3 Bedrooms • 3 Bathrooms
$3,143 - $15,714/nt
Caro, St. Barts, Gouverneur,
10 Guests • 5 Bedrooms • 5 Bathrooms
$3,500 - $13,571/nt
Ginger, St. Barts, Petite Saline,
10 Guests • 5 Bedrooms • 5 Bathrooms
$2,143 - $9,286/nt
Bastide, St. Barts, Lurin,
6 Guests • 3 Bedrooms • 3 Bathrooms
$4,286 - $17,143/nt
Ciel D’Azur, St. Barts, Anse des Cayes,
12 Guests • 6 Bedrooms • 7 Bathrooms
$1,929 - $7,857/nt
Acamar, St. Barts, Toiny,
6 Guests • 3 Bedrooms • 3 Bathrooms
$857 - $3,429/nt
Villa Abby, St. Barts, Vitet,
6 Guests • 3 Bedrooms • 3 Bathrooms
$1,500 - $4,130/nt
Villa Islander, Turks and Caicos, Grace Bay,
10 Guests • 4 Bedrooms • 4.5 Bathrooms
$2,795 - $28,500/nt
Aquamare Estate, Virgin Gorda, Mahoe Bay,
36 Guests • 15 Bedrooms • 15 Bathrooms
$3,950 - $8,580/nt
Los Corales 13 – La Sirena, Dominican Republic, Punta Cana,
16 Guests • 8 Bedrooms • 6.5 Bathrooms
$5,720 - $9,290/nt
Sirena Blue, Dominican Republic, Punta Cana,
14 Guests • 5 Bedrooms • 5 Bathrooms
$1,000 - $2,857/nt
Mer Soleil, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$1,142 - $4,645/nt
Azur Dream, St. Martin, Terres Basses,
14 Guests • 7 Bedrooms • 7 Bathrooms
$4,800 - $8,000/nt
Tip of the Tail, Turks and Caicos, Turtle Tail,
12 Guests • 5 Bedrooms • 6 Bathrooms
$2,714 - $6,000/nt
Belle Etoile, St. Martin, Terres Basses,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$1,429 - $4,286/nt
Casa Cervo, St. Martin, Baie Rouge, Terres Basses,
10 Guests • 5 Bedrooms • 5 Bathrooms
$1,000 - $3,500/nt
Ambiance, St. Martin, Terres Basses,
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$6,429 - $19,286/nt
Le Reve, St. Martin, Baie Rouge, Terres Basses,
14 Guests • 7 Bedrooms • 7 Bathrooms
$2,640 - $7,900/nt
Sambarela, Dominican Republic, Cap Cana,
18 Guests • 8 Bedrooms • 8.5 Bathrooms
$14,000 - $32,000/nt
Ani Anguilla, Anguilla, Limestone Bay,
20 Guests • 10 Bedrooms • 12 Bathrooms
$6,460 - $9,680/nt
Las Hamacas, Dominican Republic, Cap Cana,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$5,250 - $8,000/nt
Los Corales 28, Dominican Republic, Punta Cana,
16 Guests • 7 Bedrooms • 7.5 Bathrooms
$2,970 - $8,000/nt
Yarari Royale, Dominican Republic, Cap Cana,
20 Guests • 9 Bedrooms • 9.5 Bathrooms
$3,200 - $7,000/nt
Moon Reach, Barbados, The Garden,
10 Guests • 5 Bedrooms • 5 Bathrooms
$1,800 - $3,200/nt
The Westerings, Barbados, Royal Westmoreland,
14 Guests • 6 Bedrooms • 6 Bathrooms
$1,000 - $3,500/nt
Calliaqua, Barbados, Sugar Hill,
10 Guests • 5 Bedrooms • 5 Bathrooms
$2,500 - $4,500/nt
Coco De Mer, Barbados, Sandy Lane,
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$2,000 - $4,500/nt
Kailani, Barbados, St. James,
10 Guests • 5 Bedrooms • 5.5 Bathrooms
$3,200 - $14,500/nt
Altamer – Antilles Pearl, Anguilla, Shoal Bay West,
10 Guests • 5 Bedrooms • 6 Bathrooms
$1,300 - $2,800/nt
Moon Dance, Barbados, Sandy Lane,
12 Guests • 6 Bedrooms • 6 Bathrooms
$1,430 - $2,200/nt
Klairan, Barbados, Sandy Lane,
8 Guests • 4 Bedrooms • 5 Bathrooms
$1,900 - $2,900/nt
Bohemia Sandy Lane, Barbados, Sandy Lane,
10 Guests • 5 Bedrooms • 8 Bathrooms
$1,200 - $2,350/nt
Alila, Barbados, Sandy Lane,
8 Guests • 4 Bedrooms • 4 Bathrooms
$7,900 - $24,500/nt
Nevaeh, Anguilla, Long bay,
20 Guests • 9 Bedrooms • 8 Bathrooms
$9,000 - $35,000/nt
The Great House, Barbados, St. Peter,
30 Guests • 12 Bedrooms • 12 Bathrooms
$2,000 - $8,000/nt
Sandcastle, Anguilla, Limestone Bay,
12 Guests • 5 Bedrooms • 7 Bathrooms
$1,850 - $3,571/nt
Sandcastle Beach House, Anguilla, Limestone Bay,
8 Guests • 4 Bedrooms • 4.5 Bathrooms
$1,275 - $3,450/nt
Sweet Spot, Jamaica, Runaway Bay,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$14,000 - $37,000/nt
Ani Dominican Republic, Dominican Republic, Rio San Juan,
28 Guests • 14 Bedrooms • 15.5 Bathrooms
$2,572 - $4,715/nt
Malatai, Jamaica, Ocho Rios,
16 Guests • 8 Bedrooms • 8 Bathrooms
$1,714 - $3,929/nt
Hidden Bay, Jamaica, Runaway Bay,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$4,400 - $5,500/nt
Buttonwood Reef, Jamaica, Ocho Rios,
12 Guests • 6 Bedrooms • 6.5 Bathrooms
$1,330 - $1,475/nt
Sea Biscuit, Jamaica, Ocho Rios,
6 Guests • 3 Bedrooms • 3 Bathrooms
$4,000 - $5,900/nt
Canoe Cove, Jamaica, Ocho Rios,
14 Guests • 7 Bedrooms • 7.5 Bathrooms
$1,429 - $3,143/nt
Four Winds, Jamaica, Ocho Rios,
10 Guests • 5 Bedrooms • 5 Bathrooms
$2,429 - $5,000/nt
Flower Hill, Jamaica, Montego Bay,
16 Guests • 6 Bedrooms • 14 Bathrooms
$1,558 - $2,858/nt
Villa Rosa, Jamaica, Montego Bay,
11 Guests • 4 Bedrooms • 6.5 Bathrooms
$8,750 - $10,750/nt
Emerald Pavilion, Turks and Caicos, Grace Bay,
12 Guests • 5 Bedrooms • 5.5 Bathrooms
$7,750 - $21,000/nt
Coral Pavilion, Turks and Caicos, Grace Bay,
10 Guests • 5 Bedrooms • 6 Bathrooms
$7,000 - $18,000/nt
Haven House, Turks and Caicos, Long Bay,
12 Guests • 6 Bedrooms • 6 Bathrooms
$2,970 - $8,056/nt
Arrecife Royale, Dominican Republic, Punta Cana,
20 Guests • 9 Bedrooms • 9.5 Bathrooms
$7,000 - $18,000/nt
Bajacu, Turks and Caicos, Ocean Drive,
12 Guests • 6 Bedrooms • 6 Bathrooms
$3,785 - $13,500/nt
Baraka Point, Virgin Gorda, Nail Bay,
16 Guests • 6 Bedrooms • 6.5 Bathrooms
$2,100 - $4,750/nt
Indigo (formerly Greatview), Jamaica, Montego Bay,
16 Guests • 8 Bedrooms • 8 Bathrooms
$7,300 - $24,000/nt
Coral House, Turks and Caicos, Grace Bay,
10 Guests • 7 Bedrooms • 9 Bathrooms

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Toll Free: 1-888-277-8882
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THE SHELDON JAMES WAY

Don’t trust your precious time off to just anyone. Sheldon James has traveled to the Caribbean islands countless times and vetted each home and on-site partner. We will work with you before, during and after your stay to ensure that your villa stay isn’t just a vacation but an experience to remember. 

Our guest-first focus

You’re always our top priority–we’ve got you covered on all your travel needs before, during and after your stay.

Hand-selected villas

Our standards are high. Each and every villa we offer has been visited or thoroughly reviewed by a member of our team.

A trusted network

We only work with partners we know and trust, so you can count on them to reflect our values and standards.

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