New Destinations

CaribbeanDays is pleased to announce new destination opportunities to our guests! New listing availabilities will be listed here as we acquire the information.

Contact us for availability and booking opportunities.

CaribbeanDays Welcomes::


Part of the British Virgin Islands, Tortola is truly nature’s little secret. Villa guests can explore the quiet island by foot or take a jeep around the rolling hills and beautiful scenery. Tortola is also a great place for sailing and yachting around the tranquil beaches, including gorgeous Cane Garden Beach and Brewers Bay. No matter how you spend your time, a CaribbeanDays villa in Tortola is pure escapism.

Falcon’s Nest at Peter Island Vacation Rental


Jamaica is a large island with lots to do and see. Here are a few recommendations to get you started:

See historic sites: the ruins of the 17th-century Fort Montego overlook the harbor. The Georgian Town Houses used to be the residences of wealthy merchants and planters, now occupied by restaurants (Town House and Georgian House). These restored plantation houses of Greenwood and Rose Hall are over 200 years old. Daily guided tours provide a glimpse of life on a sugar plantation. Port Royal, once the headquarters of the British navy in the Caribbean, and a pirate base prior to that, is now a fishing village. Attractions include military forts, armaments and artifacts. The 200-year old great house is the centerpiece of the 300-acre Marshall’s Pen cattle ranch. Guided tours showcase antiques, stamp and shell collections, and the wildlife sanctuary.

Montego Bay, Jamaica

GoldenEye Beach and Lagoon Villas – Ocho Rios, Jamaica


Just off the coast of Florida, the Bahamas (made up of 700 islands!) is an ecological oasis waiting to be explored. There are intra-island flights, as well as ferry services and personal yachts available for you to island-hop and enjoy the unique aspects of each island. You’ll surely want to visit Nassau, the nation’s capital, and Paradise Island, which offer a distinct blend of international glamour and tropical paradise. You can relax and take a dip in the ocean, swim with dolphins, visit 18th century fortresses, and shop. Enjoy haute cuisine at one of the many restaurants and taste a Bahamas specialty — conch — or have your own private chef prepare your favorite meal. And if you’re a night-owl, there are an array of nightclubs, bars, and casinos to keep you busy. Whatever you choose to do during your Bahamas villa vacation, your luxury villa rental will provide a picture-perfect setting for it all.

SeaBreeze at Fowl Cay, Bahamas

The Villas at Fowl Cay – Exumas Villa Rental

Little Whale Cay

Dominican Republic

Whether you’re looking for a romantic escape, family getaway, or cultural experience, a stay in a Dominican Republic villa offers something for everyone. From cactus-filled deserts to mountain ranges, dramatic waterfalls, lush rainforests, and more than 800 miles of coastline offering some of the Caribbean’s most beautiful beaches, the Dominican Republic features a range of lovely settings for you to enjoy. Go whale watching, shop for unique local crafts, spend an afternoon at a museum, or try one of the many incredible water sports available, include surfing, diving, and snorkeling. For golf lovers, the Dominican Republic offers three world renowned courses, including the #1 rated golf resort in the Caribbean by Travel + Leisure magazine. The Dominican Republic is also home to Santo Domingo, a historic gold mining town featuring the Western Hemisphere’s first cathedral, monastery, and court.

Arrecife 23 at Punta Cana Resort

Tortuga Bay C33 at Punta Cana Resort


Visitors flock to Antigua’s secluded beaches kissed with powder-soft sand and crystal-clear waters. Located in the middle of the Caribbean’s Leeward Islands, Antigua’s neighbors to the North and West are Nevis, St. Kitts, St. Barts, and St. Martin; to the South are Montserrat and Guadaloupe. Known as a major sailing hub, there are many natural anchorages and tiny surrounding islands for exploring. You can relax on the beach, take a day for a sailing adventure, sightsee, and shop. At the end of the day, you’ll be able to wind down and enjoy a delectable meal at one of Antigua’s fine dining establishments or hire a private chef for a customized meal in the privacy of your villa.

Sea Hare Harbour at Jumby Bay Vacation Rental


Aruba is an independent island owned by The Netherlands, and is located just 17 miles north of Venezuela in the Caribbean Sea. Aruba is also part of the ABC islands, consisting of Aruba, Bonaire, and Curacao, which are also known as “The Dutch Islands”. Aruba has a dry and arid climate, that is warm all year round, making vacations possible at any time. So don’t miss your chance to escape to this island paradise and enjoy a relaxed lifestyle on its beautiful beaches.

Flamboyant 28 at Tierra del Sol – Aruba

Allamanda 5 at Tierra del Sol

Trinitaria 54 at Tierra del Sol – Aruba
Riviera Maya, Mexico

A Mexican Paradise! This strip of Caribbean coastline on the Yucatán Peninsula is one of Mexico’s most popular vacation destinations for good reason. In addition to heavenly beaches – think powder-soft sand and warm, turquoise water – there are plenty of one-of-a-kind attractions to discover. Explore Mayan villages and caves, swim by the only archaeological site on the sea, and snorkel along the largest coral reef system in the Northern Hemisphere.

Azul Villa Carola

El Patron Luxury Villa

Costa Rica

Costa Rica is the most popular travel destination in Central America for a reason. Costa Rica has it all: beautiful beaches, lush rainforests, and 5% of the entire world’s biodiversity! There are beautiful resorts all over the country, and plenty of opportunities to experience the culture and its ‘Pura Vida’ state of mind (“Pure Life” in English). This destination is great for all types of travelers, from families to solo adventure seekers. With Caribbean and Pacific coastlines, Costa Rica is wonderful for those who enjoy the beach and water sports. But don’t miss the inland adventures! Costa Rica is arguably the adventure capital of the Americas, and inland you will find volcano hikes, zip lines, hanging bridges, ATV tours and much more.

Casa Big Sur Villa – Dominical, Costa Rica

Exclusive Adventure in Costa Rica by CaribbeanDays


Italy is a peninsula nation located in southern Europe. Due to its geographical features, it is often called lo Stivale “The Boot”. Italy was the home to famous Renaissance figures like Leonardo da Vinci and Michaelangelo. The northern region of Italy consists mainly of the Alps, while the southern region hosts a Mediterranean feel. Major cities like Rome, Venice, Florence, Milan, and Naples all call Italy their home, each with its very own distinct history, culture, and atmosphere. Explore the famous Vatican City or venture south to the picturesque Amalfi Coast; your perfect Italian adventure awaits you.

Bella Roma – Italy

Tuscany, Italy

Tuscany is overflowing with natural, architectural, and artistic masterpieces. The birthplace of Italian Renaissance is home to rolling hills, majestic cypress trees, miles of sandy coastline, and beautiful vineyards in addition to the world’s finest art center, Florence. Stay in a rustic yet elegant villa enjoying life’s greatest pleasures: sprawling countryside, simple, fresh cuisine, and Italy’s finest wines.

Aiola Villa – Tuscany, Italy – New Destination

Orfea Villas in Lucca – Tuscany, Italy

Villa Machiavelli – Chianti Classico, Florence, Italy

Apulia, Italy!

The Valle d’Itria in Apulia is also known as Valle dei Trulli – Trullos’ Valley (trullo is a version of dome house), a UNESCO World Heritage Site since 1996. The magical atmosphere created by its characteristic white constructions with stone conic roofs immersed in timeless olive groves and Mediterranean vegetation is charming visitors from all over the world. Valle d’Itria is also famous for the natural beauty of its towns, white beaches, deep caves, fantastic cuisine and warm hospitality…and this is just to name a few!

Tria – Bravo Villas Italy

Hiera – Bravo Villas, Italy

Sorrento, Italy!

The Sorrentino coast welcomes you with sites of extraordinary natural beauty and fantastic views of Mount Vesuvius and the Gulf of Naples, in an area that stretches from Castellammare di Stabia to Sant’Agata dei Due Golfi.
Sorrento, the most relevant city of the area, is a favorite destination for many, thanks to a magic combination of quaint narrow streets, baroque churches, mild climate, verdant gardens and excellent hospitality.

Villa Lika – Sorrento, Italy

Amalfi Coast of Italy

The Amalfi Coast is 25 miles of awe-inspiring Mediterranean coastline. Whether you find yourself in one of its little hillside villages, in the middle of a lemon grove or hanging over its shimmering harbors, here la Dolce Vita appears timeless. While among the cities of the Amalfi Coast, Positano has a more international appeal and a dramatic, beautiful scenery, do not underestimate the Sorrento Coast, with its Old World graciousness and a unique local flair. A few miles off the coast is the island of Capri, sporty and elegant, an ideal destination for those who love the sea but crave the excitement of being on a famous island.

Ambita Villa – Amalfi Coast, Italy

Sicily, Italy

Sicily, like all regions of Italy, has its own rich and unique culture, especially with regard to the arts, music, literature, cuisine, architecture and language. From ancient times Sicily has been conquered by many powerful civilizations coming from all sides of the Mediterranean and from the distant north. Because of its rich and varied past, Sicily today is an amalgam of all these various artistic and architectural influences that have been absorbed during the centuries creating something extraordinary you will be charmed by. It is impossible to list here all the great things Sicily has to offer – one must visit the island and try himself, one must meet the people, eat their food and smell the air to really understand what Sicily is all about.

Villa Olida – Sicily, Italy

The French Riviera

Follow the trail of famous painters at the Matisse Museum in Nice, visit the 16th century Saint-Elme Citadel at Villefranche-sur-Mer, and swim, snorkel, and sunbathe on any of the region’s hundreds of beautiful beaches. At night, the cities of Cannes, St. Tropez and Monte Carlo come alive with fabulous restaurants, prime shopping promenades and endlessly entertaining people-watching. The French Riviera is one of the world’s foremost playgrounds for jetsetters and celebrities – you may just run into your favorite film star.

CaribbeanDays Welcomes The French Riviera


Ireland is an island in the North Atlantic. It is separated from Great Britain to its east by the North Channel, the Irish Sea, and St George’s Channel. Ireland is the second-largest island of the British Isles, the third-largest in Europe, and the twentieth-largest on Earth.

*NEW* CaribbeanDays can book you a Castle in Ireland!


Nothing says “tropical getaway” like a luxurious villa vacation on the idyllic islands of Hawaii. Our Hawaiian villas are surrounded by the scenery of dreams: pristine white-sand beaches, blue lagoons, volcanic peaks, lush rainforests, and cascading waterfalls. When you’re not lounging on the golden sand, try your hand at snorkeling, scuba diving, or surfing, or simply bask in the watercolor sunsets from the comfort of your private pool.

Tours and Adventures in Hawaii by CaribbeanDays

Palm Villa 140B

A Look at Disney’s Magical Touch in Hawaii

Villas at Koloa Landing, Poipu Beach, Hawaii

Sapphire Seas Beach Estate


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Not sure where to start your search for a Caribbean villa rental?

Contact a CaribbeanDays villa specialist today! Having visited each and every Caribbean island many times, our specialist can guide you in choosing the right island and villa for your getaway. Fill out the form below to contact a specialist and get started.

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