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At Wailea Beach Villas
Sandy Surf K508
3 bedroom 3 bath
$1,395–$3,450 / night
Sucrier at La Samanna
3 bedroom 3.5 bath
$3,000 / night
Crow's Nest at
4 bedroom 4 bath
$5,880–$11,500 / night
- Anguilla (46 villas) Anguilla villas offer a wide array of styles inspired by Mediterranean architecture and Miami art-deco. Our homes range in size from 1-16 bedrooms, perfect for a romantic getaway for two, or a family gathering. Most of our Anguilla villas are located hillside with spectacular views of the rocky shoreline and crashing waves of the sea, or are located on the beach, just steps away from the Caribbean’s most magnificent water.
- Antigua (34 villas) Retreat to an Island Hideaway's Antigua villa to relax in the sun on the powdery soft sand of the secluded beaches and to swim in the clear blue water. Our Antigua villas are primarily located just two miles from the coast of the mainland in the exclusive Jumby Bay Resort. You can enjoy the luxury of your private villa and receive top-notch services and amenities. Antigua, known as a major sailing hub, also offers ample opportunity to take day-long sailing adventures, to go diving, or even to explore the natural anchorages and tiny surrounding islands. Shop, dine, relax or play – you can do it all in Antigua.
- Bahamas (14 villas) The islands of the Bahamas are a breathtaking villa destination. Explore the islands of the Bahamas, replete with pink and white sand beaches and miles of clear blue water. You will truly enjoy pure relaxation in your Bahamas villa.
- Barbados (265 villas) The calm west coast, known for its fantastic beaches, is the perfect place for your beachfront villa. The rugged east coast provides a slightly different villa experience, overlooking the incredible turquoise sea. Many of our villas are located in Speightstown, Sandy Lane, and Sugar Hill, and range in size from 1-10 bedrooms. Our Barbados villas are airy and spacious, quaint and comfortable, and range in style from a cozy cottage to a Caribbean chic estate.
- Belize (5 villas) Island Hideaways offers luxury villa rentals in some of the most desirable locations in Belize. With over 25 years of experience matching travelers to luxury villa rentals, our professional villa specialists will help you select the perfect villa for the vacation you have in mind.
- Cabo San Lucas (70 villas) Los Cabos, Mexico is comprised of two towns: Cabo San Lucas and San Jose Del Cabo. Los Cabos has long been visited for its famous world-class golf courses, breathtaking, underwater caves, and lively nightlife scene, but as you will discover, that is just the beginning of what’s in store. With luxurious Los Cabos villas from Island Hideaways all around the area, you can rest assured that you are well suited for a Mexican villa vacation of a lifetime.
- Costa Rica (72 villas) Soaring through the rainforest on a zip line, diving in vibrant coral reefs, sunbathing on nearly deserted white-sand beaches—it’s all just the beginning of what’s in store for your Costa Rica villa vacation. This unspoiled Central American hot spot is rich in natural wonders, with a diversity of landscapes that make it perfect for adventure-seekers and relaxation-lovers alike. At Island Hideaways, you’ll find an array of lavish villa rental properties that let you experience all the area has to offer.
- Dominican Republic (82 villas) The Dominican Republic is a haven for those seeking a culturally and ecologically rich Caribbean experience. Island Hideaways’ luxury Dominican villas are located in a range of beautiful settings including cactus-filled deserts, mountain ranges, dramatic waterfalls, and lush rainforests.
- Grenada (4 villas) Known as the “island of spice,” Grenada overflows with sweet scents of nutmeg, cinnamon, clove and vanilla; but it’s not only the authentic fragrances that make this tropical paradise a special mix of sweet spiciness. The island people radiate with a colorful kindness and a simple celebratory lifestyle, representing the true spice of the land. The tiny cluster of islands is located northwest of Trinidad and Tobago. Its private villas are hidden within jungles of palms, amidst stunning forests of hibiscus and on unspoiled stretches of white-sand beaches. For a rejuvenating escape filled adventure and a deeply warm culture, visit Grenada.
- Hawaii (The Big Island) (50 villas) The Big Island of Hawaii is known for its waterfalls, rainforests, volcanoes and beautiful villas. Those seeking the perfect villa destination to go snorkeling among dolphins and colorful tropical fish should visit Kealakekua Bay. Our Hawaii villa rentals are perfect for any occasion, including weddings, honeymoons, family gatherings, trips with friends. Depending on your preference, you can reside on a hillside with panoramic views of turquoise ocean reef and rainbow-kissed mountains, or on the beach, just steps away from the pristine sand and crystal blue water.
- Jamaica (123 villas) Jamaica is one of the most popular villa rental destinations in the Caribbean. Known for its friendliness, beauty, and laid-back lifestyle, Jamaica is the perfect island getaway. Our villas range in size, from cozy private villas perfect for two, to expansive villa estates that can easily accommodate an extended family of twenty. In addition to the luxury of space, the villas also offer other amenities. Each Jamaica villa has its own personal cook, so guests can savor authentic Jamaican cuisine like jerk chicken or enjoy their own favorite dishes prepared daily.
- Kauai (2 villas) Verdant cliffs framed by sapphire seas, deep-red canyons, and over 50 miles of pristine beaches make the Hawaiian Island of Kauai a vision of paradise. With its dramatic beauty and laid-back atmosphere, the allure of “The Garden Island” is undeniable. A luxurious villa from Island Hideaways offers the perfect Kauai escape, putting lush tropical rainforest and idyllic ocean vistas right in your own backyard.
- Maui (52 villas) Maui is a rainbow landscape of white, black, and red sand beaches, green and bamboo forests, and gorgeous blue skies. Villa vacationers on Maui will not want to miss visiting the “pineapple island” of Lanai, and strolling down the streets in the town of Lahaina, visiting art galleries before an afternoon cocktail in their villa. Our Hawaii villa rentals are perfect for any occasion, including weddings, honeymoons, family gatherings, trips with friends. Depending on your preference, you can reside on a hillside with panoramic views of turquoise ocean reef and rainbow-kissed mountains, or on the beach, just steps away from the pristine sand and crystal blue water.
- Oahu (9 villas) Oahu is filled with a mix of natural and cultural wonders. The world-famous Waikiki beach is a tropical playground. Nature lovers will enjoy a walk through Oahu’s tropical rainforests, admiring the flora and viewing the colorful birds. Our Hawaii villa rentals are perfect for any occasion, including weddings, honeymoons, family gatherings, trips with friends. Our Hawaii villas range in size from one to six bedrooms. In addition, some of our Hawaii villas offer maid service and a variety of amenities including a pool, gourmet kitchen, cable TV, WiFi, and indoor/outdoor dining.
- Private Islands (4 villas) Who hasn't fantasized about getting away from it all on your own Caribbean private island? Just you, the sand, the surf, the beauty, the tranquility. A stay on a private island is truly the ultimate luxury villa vacation. If this is your idea of a dream getaway, you can make it a reality by renting a private island in the Caribbean from Island Hideaways.
- Puerto Vallarta (43 villas) Located on Mexico’s Pacific Coast and in the heart of Banderas Bay, lies the cultural gem and vacation hot-spot of Puerto Vallarta, Mexico. Amazing weather, gold-sand beaches, and indigo waters are just the beginning of the region’s treasure trove of characteristics waiting to be discovered by eager tourists and visitors.
- Puerto Rico (8 villas) Nestled in the northeast corner of the Caribbean, Puerto Rico is home to a broad range of exciting activities you can enjoy with your villa stay.
- Punta Mita (51 villas) Bordered by indigo waters, lush tropical forests and the majestic Sierra Madre Mountains, Punta Mita is a secluded, intimate destination sure to transport you from the stresses of everyday life. This small beachfront peninsula is home to gentle sea breezes and a warm, tropical climate year-round. From surf lessons and coral reef snorkeling to beachside horseback riding and world-class golf, Punta Mita offers unparalleled options for fun and relaxation. Our private Punta Mita villa rentals are in the area’s most desirable and exclusive locations, such as the Four Seasons Resort, Las Palmas and Ranchos Estates.
- Riviera Maya (50 villas) The multicultural and adventure-rich region known as Riviera Maya sits along the Yucatan’s Caribbean Coast and reaches 236 miles from Cancún to Chetumal. With its rich culture, ancient structures, and gorgeous Tropical climate, Riviera Maya villas are the perfect way to indulge in a Mexican villa escape filled with adventure and excitement.
- St. Barts (320 villas) Villa rentals on St. Barts are the primary form of accommodation and Island Hideaways provides a myriad of villa options. Our St. Barts villas are located in the hills, with fabulous views of multi-color lagoons, volcanic peaks, and yachts docked in the harbor, or are beachfront properties on one of the 22 unspoiled beaches on the island.
- St. Croix (24 villas) St. Croix villas are located on the east side of the island, with picturesque surroundings of the rocky, arid coast, on the west side of the island, with lush vegetation, or on a beachside surrounded by rolling hills and pastures. Our St. Criox villas are between two and six bedrooms and all feature a pool.
- St. John (59 villas) Island Hideaways’ St. John’s villas are located on a hillside with panoramic views of the Caribbean Sea, alongside the waterfront, or beachfront with pristine white sand at your doorstep. Bordered by seagrapes, Maho trees and coconut palms, and filled with white, satiny sand, St. John villas are pure paradise. Villas in St. John range in size from one to eight bedrooms and most have their own private pool.
- St. Lucia (49 villas) Our collection of St. Lucia villa rentals includes hillside homes with gorgeous views of the calming waters and nearby islands along with water and beachfront properties. Each villa has its own distinct charm ranging from a 150-year-old restored French colonial plantation house to a intriguing castle-like façade, from a Spanish-style villa with a courtyard at its center to an exotic villa blending traditional West Indian and east architecture.
- St. Martin (140 villas) Island Hideaways’ St. Martin villas are located on both the more secluded French-side and more active Dutch-side and are both hillside and beachfront.Each villa is uniquely and elegantly decorated and many include daily maid service. Our St. Martin villas are perfect for all types of vacations and range in size from 1 to 11 bedrooms and almost all of the villas feature a pool.
- St. Thomas (36 villas) St. Thomas, the most developed and populated of the U.S. Virgin Islands, has some of the most spectacular villas in the Caribbean. St. Thomas villas are the ideal vacation home. Ranging in size from one to 10 bedrooms, St. Thomas private villa homes accommodate trips for all occasions. Almost all St. Thomas villas feature a pool and maid service. Island Hideaways’ St. Thomas villas are located on the hillside with magnificent views of the turquoise water or are beachfront.
- Tortola (20 villas) Our Tortola villas are magnificent for an island getaway. They range in size from one to eight bedrooms, so they are great for a holiday for two or a vacation with friends and family. Many Tortola villas are situated on a hilltop, overlooking the ocean, or are on the beach or waterfront. Our private villas in Tortola are perfect for ultimate relaxation. Some of our larger villas come with their own state-of-the-art gyms and almost all of our Tortola villas have a private pool. You will truly be pampered.
- Turks and Caicos (57 villas) A Turks & Caicos villa is perfect for honeymooners, friends, and families. Villa vacation homes in Turks & Caicos range in size from two to six bedrooms and are located on the hillside, beachfront, or waterfront. Many are equipped with a pool. Maid service and a personal cook can be provided as well.
- Virgin Gorda (43 villas) Virgin Gorda villas are ideal for a romantic getaway, wedding, special occasion, or just a vacation with friends or family. Our Virgin Gorda villas range in size from two to six bedrooms and are all beautifully and tastefully decorated. Almost all of our Virgin Gorda villas are equipped with a private pool and amenities include indoor/outdoor dining, a fully-equipped kitchen, and even a private gym in some of our larger villas. Many of our villas have access to a spa and tennis court. Most villas include a daily maid service and a personal cook can be provided upon request, so all you have to do is relax.
- Anguilla Villas
- Antigua Villas
- Bahamas Villas
- Barbados Villas
- Belize Villas
- Cabo San Lucas Villas
- Costa Rica Villas
- Dominican Republic Villas
- Grenada Villas
- Hawaii-Big Island Villas
- Jamaica Villas
- Kauai Villas
- Maui Villas
- Oahu Villas
- Private Islands Villas
- Puerto Vallarta Villas
- Puerto Rico Villas
- Punta Mita Villas
- Riviera Maya Villas
- St. Barts Villas
- St. Croix Villas
- St. John Villas
- St. Lucia Villas
- St. Martin Villas
- St. Thomas Villas
- Tortola Villas
- Turks and Caicos Villas
- Virgin Gorda Villas
- Architectural Digest
- Corporate Villas
- Family Villas
- Golf Villas
- Historic Estates
- Honeymoon & Romantic
- Pet Friendly
- Private Island
- Resort Villas
- Tennis Villas
- Wedding Villas
For over 25 years, Island Hideaways has represented hundreds of luxurious villas and private islands throughout the Caribbean and Hawaii.