×
Caribbean Villas by Location
Caribbean Villas by Topic
×
Contact WhereToStay.com

Others' claim to be Caribbean experts. We prove it. Every call. Every email, Every chat.

×
Your Favorites
Hidden favorites

Specials by Destination

Featured Specials

Free Night Stay! - St. Martin

Not Combinable with other Specials Available on 6 or 11 Bedroom Rates.

Offered at Mes Amis 11BR/11.5BA on St. Martin

Holiday Offer! - St. Barts

Offered at Jocapana Villa 3BR/3BA on St. Barts

Holiday Offer! - St. Barts

Offered at Jocapana Villa 3BR/3BA on St. Barts

Free Night Stay! - St. Barts

Offered at Cumulus Villa 7BR/6BA on St. Barts

Savings in February!! - Tortola, BVI

Stay 7 nights and receive a 20% discount!

Offered at Outer Banks 5BR/5.5BA on Tortola, BVI

Savings in February!! - Tortola, BVI

Stay 5 or 6 nights and receive a 15% discount!

Offered at Outer Banks 5BR/5.5BA on Tortola, BVI

Savings in January!! - Tortola, BVI

Stay 7 nights and receive a 25% discount!

Offered at Outer Banks 5BR/5.5BA on Tortola, BVI

Savings in January!! - Tortola, BVI

Stay 5 or 6 nights and receive a 20% discount!

Offered at Outer Banks 5BR/5.5BA on Tortola, BVI

7th Night Free! - Virgin Gorda, BVI

Or stay 14 nights and pay for 12!

Offered at Baraka Point 5BR/5.5BA on Virgin Gorda, BVI

Savings in January! - St. Martin

Not combinable with other Special Offers

Offered at Acqua Villa 5BR/5.5BA on St. Martin

Free Night Stay! - St. Martin

Not combinable with other Special Offers

Offered at Acqua Villa 5BR/5.5BA on St. Martin

Free Night Stay! - St. Martin

Cannot be combined with any other discount or promotion !

Offered at Bahia Blue 4BR/4BA on St. Martin

h - St. Barts

Offered at The View 4BR/4BA on St. Barts

Holiday Promotion!! - St. Barts

Offered at Cumulus Villa 7BR/6BA on St. Barts

2016 Promotion! - Turks and Caicos

7 Night Minimum Stay

Offered at Somerset On Grace Bay - 1 Bedroom 1BR/1.5BA on Turks and Caicos, Somerset On Grace Bay - 2 Bedroom 2BR/2BA on Turks and Caicos, Somerset On Grace Bay - 3 Bedroom 3BR/3BA on Turks and Caicos, Somerset On Grace Bay - 5 Bedroom Penthouse 5BR/0BA on Turks and Caicos

Military Discount!! - Virgin Gorda, BVI

Subject to nightly minimums per villa Guest must provide Military Credentials on confirmation in order for discount to be applied Offer does not apply to existing reservations. Not combinable with any existing special offers, promotions, or special one-time considerations by owner

Offered at Sunset Watch Villa 3BR/2BA on Virgin Gorda, BVI

Military Discount!! - Virgin Gorda, BVI

Subject to nightly minimums per villa Guest must provide Military Credentials on confirmation in order for discount to be applied Offer does not apply to existing reservations. Not combinable with any existing special offers, promotions, or special one-time considerations by owner

Offered at Sunset Watch Villa 3BR/2BA on Virgin Gorda, BVI

Graduation Gift - Anguilla

Mom and Dad, plan ahead and save. Surprise your graduate! •Allow your graduate to invite four friends for a never-to-be-forgotten 3 night celebration of their accomplishments. •Four living/dining areas. 33,000 gallon lagoon-style heated pool. •Suite #1 - King with second, private pool for Mom and Dad. •Suite #2 - Your graduate in a sumptuous king. •Suite #3 - Two queens - two friends. •Suite #4 - Two twins - two friends. •Indoor/outdoor sound system for the kids’ iPods. •Kylon will take you and your graduates on a tour of the most popular beach bars by day and nights. •See the Dune where Jimmy Buffett performed his last CD. Elvis’ for sunset. The Pumphouse for live music and dancing. Discover where the stars hang out. •Daily housekeeping and beach attendant for chairs and umbrellas. •Includes 10% tax and 10% service charge.

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Graduation Gift - Anguilla

Mom and Dad, plan ahead and save. Surprise your graduate! •Allow your graduate to invite four friends for a never-to-be-forgotten 3 night celebration of their accomplishments. •Four living/dining areas. 33,000 gallon lagoon-style heated pool. •Suite #1 - King with second, private pool for Mom and Dad. •Suite #2 - Your graduate in a sumptuous king. •Suite #3 - Two queens - two friends. •Suite #4 - Two twins - two friends. •Indoor/outdoor sound system for the kids’ iPods. •Kylon will take you and your graduates on a tour of the most popular beach bars by day and nights. •See the Dune where Jimmy Buffett performed his last CD. Elvis’ for sunset. The Pumphouse for live music and dancing. Discover where the stars hang out. •Daily housekeeping and beach attendant for chairs and umbrellas. •Includes 10% tax and 10% service charge.

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Graduation Gift - Anguilla

Mom and Dad, plan ahead and save. Surprise your graduate! •Allow your graduate to invite four friends for a never-to-be-forgotten 3 night celebration of their accomplishments. •Four living/dining areas. 33,000 gallon lagoon-style heated pool. •Suite #1 - King with second, private pool for Mom and Dad. •Suite #2 - Your graduate in a sumptuous king. •Suite #3 - Two queens - two friends. •Suite #4 - Two twins - two friends. •Indoor/outdoor sound system for the kids’ iPods. •Kylon will take you and your graduates on a tour of the most popular beach bars by day and nights. •See the Dune where Jimmy Buffett performed his last CD. Elvis’ for sunset. The Pumphouse for live music and dancing. Discover where the stars hang out. •Daily housekeeping and beach attendant for chairs and umbrellas. •Includes 10% tax and 10% service charge.

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Graduation Gift - Anguilla

Mom and Dad, plan ahead and save. Surprise your graduate! •Allow your graduate to invite four friends for a never-to-be-forgotten 3 night celebration of their accomplishments. •Four living/dining areas. 33,000 gallon lagoon-style heated pool. •Suite #1 - King with second, private pool for Mom and Dad. •Suite #2 - Your graduate in a sumptuous king. •Suite #3 - Two queens - two friends. •Suite #4 - Two twins - two friends. •Indoor/outdoor sound system for the kids’ iPods. •Kylon will take you and your graduates on a tour of the most popular beach bars by day and nights. •See the Dune where Jimmy Buffett performed his last CD. Elvis’ for sunset. The Pumphouse for live music and dancing. Discover where the stars hang out. •Daily housekeeping and beach attendant for chairs and umbrellas. •Includes 10% tax and 10% service charge.

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Multi Generational Celebration - Anguilla

Thank you Mom and Dad for all that you do •Three generations celebrate the love and generosity of the grandparents. •3 night getaway for family of 8. •A private home comprised of three buildings intertwined by a lagoon-style pool and lush landscape. •Grandparents have a private suite with their own pool. •Chef will have welcome refreshments for the children as well as champagne to toast the grandparents. . •Welcome Caribbean barbecue with all the trimmings. •All food and beverage included for welcome cocktails and barbecue. •On-demand chef for breakfasts overlooking the beach, lunch by the pool, or dinners under the stars. •Tristan will be your butler, server and bartender. •Rental car/van included. Take the children to hear steel drums, explore a new beach, or find a 40,000 year old fossil. •Includes 10% tax and 10% service charge Not included Food and beverage other than welcome cocktail party and Caribbean barbecue.

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Multi Generational Celebration - Anguilla

Thank you Mom and Dad for all that you do •Three generations celebrate the love and generosity of the grandparents. •3 night getaway for family of 8. •A private home comprised of three buildings intertwined by a lagoon-style pool and lush landscape. •Grandparents have a private suite with their own pool. •Chef will have welcome refreshments for the children as well as champagne to toast the grandparents. . •Welcome Caribbean barbecue with all the trimmings. •All food and beverage included for welcome cocktails and barbecue. •On-demand chef for breakfasts overlooking the beach, lunch by the pool, or dinners under the stars. •Tristan will be your butler, server and bartender. •Rental car/van included. Take the children to hear steel drums, explore a new beach, or find a 40,000 year old fossil. •Includes 10% tax and 10% service charge Not included Food and beverage other than welcome cocktail party and Caribbean barbecue.

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Multi Generatioal Celebration - Anguilla

Thank you Mom and Dad for all that you do •Three generations celebrate the love and generosity of the grandparents. •3 night getaway for family of 8. •A private home comprised of three buildings intertwined by a lagoon-style pool and lush landscape. •Grandparents have a private suite with their own pool. •Chef will have welcome refreshments for the children as well as champagne to toast the grandparents. . •Welcome Caribbean barbecue with all the trimmings. •All food and beverage included for welcome cocktails and barbecue. •On-demand chef for breakfasts overlooking the beach, lunch by the pool, or dinners under the stars. •Tristan will be your butler, server and bartender. •Rental car/van included. Take the children to hear steel drums, explore a new beach, or find a 40,000 year old fossil. •Includes 10% tax and 10% service charge Not included Food and beverage other than welcome cocktail party and Caribbean barbecue.

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Multi-Generational Celebration - Anguilla

Thank you Mom and Dad for all that you do •Three generations celebrate the love and generosity of the grandparents. •3 night getaway for family of 8. •A private home comprised of three buildings intertwined by a lagoon-style pool and lush landscape. •Grandparents have a private suite with their own pool. •Chef will have welcome refreshments for the children as well as champagne to toast the grandparents. . •Welcome Caribbean barbecue with all the trimmings. •All food and beverage included for welcome cocktails and barbecue. •On-demand chef for breakfasts overlooking the beach, lunch by the pool, or dinners under the stars. •Tristan will be your butler, server and bartender. •Rental car/van included. Take the children to hear steel drums, explore a new beach, or find a 40,000 year old fossil. •Includes 10% tax and 10% service charge Not included Food and beverage other than welcome cocktail party and Caribbean barbecue.

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Romance Package - Anguilla

For the love of your life •3 night getaway for two in your own private villa. •Panoramic views and not one, but two pools overlooking the beach, just for you! •Whirlpool tub overlooking a private garden. Shower under the stars. •Bvlgari amenities, Frette linens. Surprise gifts. •Car, driver, and concierge will meet you as you arrive Anguilla. •Chef will greet you with champagne, rum punch, and appetizers. •Caribbean barbecue with chicken, ribs, grilled lobster, prepared by your own private chef. •All food and beverage for above chef services included. •Daily housekeeping. •Beach attendant to set up chairs and umbrellas •Includes 10% tax and 10% service charge

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Romance Package - Anguilla

For the love of your life •3 night getaway for two in your own private villa. •Panoramic views and not one, but two pools overlooking the beach, just for you! •Whirlpool tub overlooking a private garden. Shower under the stars. •Bvlgari amenities, Frette linens. Surprise gifts. •Car, driver, and concierge will meet you as you arrive Anguilla. •Chef will greet you with champagne, rum punch, and appetizers. •Caribbean barbecue with chicken, ribs, grilled lobster, prepared by your own private chef. •All food and beverage for above chef services included. •Daily housekeeping. •Beach attendant to set up chairs and umbrellas •Includes 10% tax and 10% service charge

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Romance Package - Anguilla

For the love of your life •3 night getaway for two in your own private villa. •Panoramic views and not one, but two pools overlooking the beach, just for you! •Whirlpool tub overlooking a private garden. Shower under the stars. •Bvlgari amenities, Frette linens. Surprise gifts. •Car, driver, and concierge will meet you as you arrive Anguilla. •Chef will greet you with champagne, rum punch, and appetizers. •Caribbean barbecue with chicken, ribs, grilled lobster, prepared by your own private chef. •All food and beverage for above chef services included. •Daily housekeeping. •Beach attendant to set up chairs and umbrellas •Includes 10% tax and 10% service charge

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

Romance Package - Anguilla

For the love of your life •3 night getaway for two in your own private villa. •Panoramic views and not one, but two pools overlooking the beach, just for you! •Whirlpool tub overlooking a private garden. Shower under the stars. •Bvlgari amenities, Frette linens. Surprise gifts. •Car, driver, and concierge will meet you as you arrive Anguilla. •Chef will greet you with champagne, rum punch, and appetizers. •Caribbean barbecue with chicken, ribs, grilled lobster, prepared by your own private chef. •All food and beverage for above chef services included. •Daily housekeeping. •Beach attendant to set up chairs and umbrellas •Includes 10% tax and 10% service charge

Offered at Bird of Paradise Villa 4BR/4.5BA on Anguilla

High Season Offer! - Turks and Caicos

Offered at Ballyhoo Cottage 1BR/1BA on Turks and Caicos

High Season Offer! - St. Barts

4 Bedrooms

Offered at Palm Springs Villa 4BR/4BA on St. Barts

High Season Offer! - St. Barts

3 Bedrooms

Offered at Palm Springs Villa 4BR/4BA on St. Barts

High Season Offer! - St. Barts

1 - 2 Bedrooms

Offered at Palm Springs Villa 4BR/4BA on St. Barts

7th Night Free! - Bahamas

Excluding all major U.S. holidays and first week of August (Lobster season opening).

Offered at Jasmine on the Isle 5BR/5BA on Bahamas

7th Night Free! - Tortola, BVI

New Bookings only! Excluding Christmas/New Year rate period.

Offered at Villa Maya 4BR/4.5BA on Tortola, BVI

Holiday Promotion! - St. Barts

Offered at Coco Rock Villa 6BR/6BA on St. Barts

La Samanna Promotion!!! - St. Martin

Free Car Rental & Free Nights Tax, insurances, gasoline, upgrade, extras … not included ! cannot be combined with any other promotion that may come into effect

Offered at La Samanna Resort - Mouette Villa 4BR/4BA on St. Martin, La Samanna Resort - Sucrier Villa 3BR/3BA on St. Martin, La Samanna Resort - Sula Sula Villa 3BR/3BA on St. Martin, La Samanna Resort - Tiaris Villa 4BR/4BA on St. Martin

La Samanna Promotion!!! - St. Martin

Free Car Rental & Free Nights Tax, insurances, gasoline, upgrade, extras … not included ! cannot be combined with any other promotion that may come into effect

Offered at La Samanna Resort - Mouette Villa 4BR/4BA on St. Martin, La Samanna Resort - Sucrier Villa 3BR/3BA on St. Martin, La Samanna Resort - Sula Sula Villa 3BR/3BA on St. Martin, La Samanna Resort - Tiaris Villa 4BR/4BA on St. Martin

January Promotion! - St. Martin

Not available over the Christmas Holidays ! Cannot be combined with any other discount or promotion ! Not available on reservation already booked.

Offered at Luna Villa 3BR/4.5BA on St. Martin

January Promotion! - St. Martin

Not available over the Christmas Holidays ! Cannot be combined with any other discount or promotion ! Not available on reservation already booked.

Offered at Azur Reve Villa 4BR/5BA on St. Martin, Belle Fontaine Villa 5BR/5BA on St. Martin, Clair de Lune Villa 4BR/4.5BA on St. Martin, Eden Villa 5BR/7BA on St. Martin, Encore Villa 5BR/5BA on St. Martin, Fields of Ambrosia Villa 3BR/4BA on St. Martin, Grand Bleu Villa 4BR/4BA on St. Martin, Grand Palms Villa 3BR/3BA on St. Martin, Hacienda Villa 4BR/3BA on St. Martin, Interlude Villa 5BR/4BA on St. Martin, Jacaranda Villa 4BR/4BA on St. Martin, Just in Paradise Villa 3BR/3.5BA on St. Martin, L'Oasis Villa 7BR/7 1/2BA on St. Martin, La Croisette Villa 4BR/4BA on St. Martin, La Nina 2BR/2BA on St. Martin, La Pinta 4BR/4BA on St. Martin, La Provencale Villa 5BR/5BA on St. Martin, Little Jazz Bird Villa 4BR/4.5BA on St. Martin, Little Provence Villa 2BR/2BA on St. Martin, Lune de Miel Villa 2BR/2BA on St. Martin, Marine Terrace Villa 5BR/5.5BA on St. Martin, Mariposa Villa 4BR/4BA on St. Martin, Mer Soleil Villa 5BR/5BA on St. Martin, Pointe Des Fleurs Villa 4BR/4BA on St. Martin, Sol e Luna Villa 3BR/3BA on St. Martin, Terrasse de Mer Villa 4BR/4BA on St. Martin

Free Night Stay! - Anguilla

Offered at Gardenia Villa 5BR/5BA on Anguilla

INTRODUCTORY OFFER: - St. John

Save on all rentals (holidays excluded). Book now; this offer may be withdrawn at any time. New Bookings Only

Offered at Ananda Villa 2BR/2BA on St. John, Sarang Villa 2BR/2BA on St. John

January Special Rate - Turks and Caicos

Offered at Water Edge Villa 1BR/1BA on Turks and Caicos

January Special Rate - Turks and Caicos

Offered at Water Edge Villa 1BR/1BA on Turks and Caicos

Special January 2016 Rates - Turks and Caicos

Offered at Ocean Edge Villa 1BR/1BA on Turks and Caicos

Caribbean Villa and Hotel Specials

Travelers are looking for value. We continually are looking for the best deals on hotels and villas in the Caribbean. We constantly review our rates to make sure we have the lowest pricing on the web ensuring that you get the best deal. We have found these special offers, discounted rates, free nights, free car rentals, complimentary services and many other great deals! Don't see a deal or special that you are looking for? Give us a call! Our Caribbean villa experts will always work to get you the best deal possible! Call today to plan your villa vacation at 800.869.8017 (US/CAN) or 214-350-6220 (Int.) or email us at villas@wheretostay.com.

Loading...