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
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.
Featured Villa
Steele Point
Tortola, BVI featured villa
This famous ultra-deluxe estate, featured in Architectural Digest, is situated on its own private and gated 8-acre peninsula featuring 360-degree blue ocean views, a private dock for swimming, snorkeling and boating, a cliffside pool…
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.

Recent Caribbean Villa Specials
- Pay for 6 nights, Stay 7! at Nirvana Penthouse Villa (St. Martin)
- 7th night free at Seapoint Villa (Turks and Caicos)
- 7th night Free at La Percha Villa (Turks and Caicos)
- 7th night Free at Turquesa Villa (Turks and Caicos)
- 7th night Free at Calypso (Turks and Caicos)
- July/August Special - 15% discount at Emerald Beach #2 - Allamanda (Barbados)
- July/August Special - 15% discount at Emerald Beach #3 - Ixoria (Barbados)
- July/August Special - 15% discount at Emerald Beach #4 - Plumbago (Barbados)
- July/August Special - 15% discount at Emerald Beach #5 - Aspicia (Barbados)
- July/August Special - 15% discount at Bluff Cottage (Barbados)
Recent Caribbean Hotel Specials
- PROMOTION at Bleu Emeraude (St. Martin)
- Spring Fling at Jewel Dunn's River Beach Resort & Spa (Jamaica)
- Tropical Getaway at Coral Gardens (Turks and Caicos)
- White House Villa at Coral Gardens (Turks and Caicos)
- 40% Off Summer Sale at La Vista Azul Resort (Turks and Caicos)
- Summer Exclusive at Casa de Campo (Dominican Republic)
- Apartment Espoir at Apartment Espoir (St. Lucia)
- CAYMAN SUMMER SPLASH at Sunset Cove (Cayman Islands)
- CAYMAN SUMMER SPLASH at Britannia Villas (Cayman Islands)
- SUMMER SPECIAL at Hotel Le Village St Jean (St. Barts)
Most Recent Caribbean Travelers' Reviews
- I wouldn't eat here. by nursenurse24- Riu Montego Bay - All Inclusive in Montego Bay
- Tequila Sunrise Villa is paradise. by lunared26- Tequila Sunrise Villa in Anguilla
- Ginger Thomas - 4/21/12 - 4/28/12 by Lance T- Ginger Thomas in St. John, USVI
- Alexambre is a pretty good value. by dcall90- Alexambre in Orient Bay (French side)
- We enjoyed great views here. by Donna- Blue Skies Villa in St. John, USVI
- St. Charles North Caicos is now abandoned. by AlanS- St. Charles North Caicos in North Caicos
- This was our family dream vacation. by Melia W- Paprika Villa in Providenciales
- We were extremely pleased! by Jordan O- La Bagatelle Villa in Soufriere
- Amazing House--could use a bit of updating by msarwer- Tropical Shores Villa in Providenciales
- This was a wonderful family retreat. by JR D- Carlisle House in St. Croix, USVI
- Peaceful vista, pleasant stay! by Amanda S- Breezy Palms in Providenciales
- It was an upgrade from a tent - mediocre place if you are expecting a quaint cabana. by brossyg- Green Parrot Beach Houses in Belize
- Tamarind House was phenomenal! by lshak- Tamarind House in Soufriere
- This is so relaxing - and great value for money! by Zalisha- Enchanted Waters Hotel in Tobago
- This was a great hotel with wonderful hosts. by sduncanrn- Green Iguana Hotel in St. Thomas, USVI
- This is a must-see! by sgraham- La Josephine in Terres Basses (French side)
- Crystals is a real Caribbean jewel. by Remi- Crystals in Soufriere
- What a wonderful place!! by Anna G- Place de la Sol Villa in Providenciales
- This is the #1 private family getaway in the Dominican Republic! by SamanaWeddings- Sunrise Villa in Cabrera
- Our stay was private and family friendly - the perfect vacation! by Lisa S- Ocean Villas 1 Bedroom - Rio Mar Beach Resort in Northeast Coast
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!









