Caribbean villas & hotels for Caribbean vacation deals

Welcome to WhereToStay.com, the original traveler-review site. Since 1995, we've been aligning aspiring vacationers with a better image of their dream destinations by providing listings of Caribbean villas and restaurants along with real reviews from past customers. Read an overview of each destination spot and get info and reviews on hotels, restaurants, weather, entertainment, and more.

Know before you go...®

Are you searching for the perfect vacation? We help you make your dreams a reality. Find listings of Caribbean hotels and restaurants, maps, pictures, and videos to get a better understanding of exotic destinations like Anguilla, St. Lucia, St. Thomas, locales offering endless entertainment amongst miles of white-sand beaches.

Villa Rentals

Villa Rentals

Have you ever rented a private home or villa for your holiday? Luxury villas in Barbados, St. Barts, St. Thomas, St. John, St. Lucia, Jamaica, and other Caribbean locations. Find villas right on the beach or on a hill with a view.

Necker Island

Featured Villa


Necker Island

Necker Island, BVI featured villa
Surrounded by the sparkling blue Caribbean sea of the British Virgin Islands, Necker Island exudes the elegance and lifestyle of the rich and famous. You can "rent" the whole island for yourself and your…

Caribbean Villa Destinations

Want more information about an island? Get regional travel tips, entry and exit requirements and more. Each destination guide is chocked full of valuable information to plan your ultimate vacation.

caribbean map

Most Recent Caribbean Travelers' Reviews

  • Did not feel safe here... by StephanieC- Chippewa Village in Negril
  • perfect spot to chill by dneshek- Cadasse Villa in Cap Estate
  • This was a major dump. by Cindy1- Apartment Espoir in St. Lucia
  • I enjoyed my stay on the Au Naturale side of Couples. by FlagRez- Couples Sans Souci All Inclusive in Ocho Rios
  • We were extremely disappointed with our trip. by semcpa- Grand Lido Negril in Negril
  • Don't expect what they promise - it isn't there! by movika- Coral Villa in Terres Basses (French side)
  • Perfect villa by tracer- Pallina Villa in St. Thomas, USVI
  • Ours was an amazing honeymoon in Paradise. by GregJess- Natures Paradise in St. Lucia
  • We love, love, love it here! by Cathi626- Breezy Villa in Providenciales
  • Beautiful stay in paradise by Maryc- Rose of Sharon in Barbados
  • Real life was even better than the photos. by tracer- Villa Gardenia in St. Thomas, USVI
  • It was breathtakingly beautiful and peaceful. by suecowdrill- Castara Retreats in Tobago
  • We had a fantastic vacation! by sundowners- Arches in Oyster Pond (Dutch side)
  • Crystals is pure, comfortable and perfectly placed for beautiful views. by angie2009- Crystals in St. Lucia
  • I had a wonderfully relaxing vacation here. by ajackson- Negril's Idle Awhile in Negril
  • Loblolly by virgin12343- Loblolly in Virgin Gorda, BVI
  • It was amazing! by skforster- Grand Lucayan in Grand Bahama Island
  • This was a perfect holiday. by Tonia- Castara Retreats in Tobago
  • It was just perfect for a restful holiday by iliana- Grafton Beach Resort in Tobago
  • Lavender Hil is a great place in a great location! by taramyatt- Lavender Hill Suites in St. John, USVI

It's important to think about what you want in a Caribbean vacation. Are you planning a destination wedding or honeymoon? Is this a yearly outing with a group of friends? Do you want a string of beach-washed days alone with a loved one? The Caribbean has something to offer everyone Ð it's just a matter of selecting a destination.

Know before you go on vacation. To better ensure a time that aligns with your expectations, it's best to do research before taking off. It can be difficult to distinguish fact from fiction when reading online marketing material, that's why reading customer reviews are so beneficial Ð you need info that's non-biased and straightforward, and we have it for you here!

You might be thinking about the right time to take a Caribbean vacation. Mid-December through late April is the most toured time there. The weather is at its absolute best, with little chance of rain, yet the high likelihood of the presence of other tourists and higher rates asked for Caribbean villas is imminent. On the other hand, April to December is quieter, and hotel and entertainment rates drop. Pay close attention to weather patterns of particular destinations, as this is the season when storms and hurricanes are more likely to occur.

There are numerous reasons to go on Caribbean vacations. Find Caribbean hotels on private islands, go sail the open seas, make it an intimate getaway with your spouse, improve your golf and tennis game amongst days of sun, etc. It's clear you don't need too much convincing about taking a Caribbean vacation, you just want more information to make the best choice. That's where we excel and deliver.

WhereToStay.com is your virtual tour guide, providing you with all the necessary information needed to make the choice best suited to your wishes. Listings of villas in Anguilla, hotels in St. Lucia, restaurants in Barbados, and more are only a few clicks away! Get started and start knowing now!

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