Hawaii Villas & Luxury Vacation Rentals

North America  ·  USA  ·  Hawaii

315 Villas found
Hale 'Ae Kai
from $ 4500 / nt
10 4 6
Kaanapali Kahala
from $ 8250 / nt
16 8 10
Banyan Hale
from $ 9300 / nt
12 7 9
Grand Kailua Beachside Estate
from $ 6000 / nt
14 7 8
Royal Pacific Suite - Ritz Carlton
from $ 6950 / nt
4 2 2
Lanai - Molokai Residence At Montage Kapalua Bay
from $ 2545 / nt
10 4 5
Grand Residence Ocean At Montage Kapalua Bay
from $ 5830 / nt
10 4 5
from $ 5700 / nt
14 7 7
Paradise Cove Estate
from $ 7000 / nt
14 7 8
2905C Hainoa Street
from $ 900 / nt
6 3 3
from $ 3175 / nt
10 5 6
Premier Ocean Grand Residence At Montage Kapalua Bay
from $ 1845 / nt
8 3 4
Secret Cove
from $ 4500 / nt
8 4 6
Andaz Villas at Wailea
from $ 4500 / nt
8 4 5
Diamond Head Beach Villa
from $ 5000 / nt
12 5 4
Kaikuono Villa
from $ 3600 / nt
8 3 5
Villa Diamond Head
from $ 3000 / nt
10 4 6
Hale Kumalani
from $ 3500 / nt
8 4 5


Hawaii Villas & Luxury Vacation Rentals

Welcome to Hawaii, where volcanic landscapes collide into canopies of lush greenery, and white sand beaches melt into the turquoise sea. The Hawaiian archipelago has long been America’s favorite vacation destination for tropical getaways, and for good reason. Whether launching a honeymoon, family vacation, or business retreat, the state of Hawaii holds the promise of an unforgettable luxury vacation experience, catering to discerning travelers seeking the ultimate retreat to paradise. From oceanfront private vacation homes in Maui to luxury villa rentals nearby downtown Honolulu, these accommodations suit a wide range of vacation itineraries. Whether its an ocean view seen through floor-to-ceiling windows or a private terrace appointed with an infinity pool and jetted spa, Hawaii’s villas underscore the essence of an upscale tropical holiday.

Maui is one of Hawaii’s most popular vacation destinations, offering a unique version of traditional seaside relaxation to affluent travelers. Many of its beaches feature distinctive black sands, tinged from nearby volcanoes, while other shorelines offer palm-fringed white sand beaches lined with exclusive private vacation homes. Visitors seeking a day of safe swimming head to Kapalua Beach, a destination known for its tranquil waters and oceanfront luxury villa rentals. Mau’aka Beach is a mecca for discerning travelers launching aquatic daytime activities, with numerous facilities for snorkeling or swimming with sea turtles, or simply enjoying a tanning session on its soft golden sands. Lanai and Molokai are both famous for their scuba diving sites, and Ho’okipa Beach remains the world’s foremost windsurfing beach for professionals.

Discover and Enjoy Five Star Experiences In Hawaii

With so many beaches to choose from, it’s easy to see why Maui attracts droves of tourists each year to book its waterfront private vacation homes. However, the adventure inland is just as rich. Head to Lahaina to attend the Old Lahaina Luaua, where a celebratory atmosphere welcomes guests to enjoy hula dances, traditional Hawaiian food, and the hospitable populace. A day hiking the Haleakalā Crater in Haleakalā National Park is best complemented by the astounding evening sunsets that grace the volcanic landscape, while Waihe’e Ridge Trail offers another brilliant landscape for hikers and nature enthusiasts.

Hawaii Island – or Big Island – is another favorite island destination for affluent travelers seeking the ultimate tropical getaway in this state. This massive island comprises five overlapping shield volcanoes, one of which is the famous (but dormant) Mauna Key. Visitors booking luxury villa rentals in Big Island are in for a treat; visit the Hawaii Volcanoes National Park to witness active volcanoes spewing fireworks of lava across the landscape. Aside from these formidable natural monuments, Big Island offers myriad other outdoor adventures to please active vacationers. From enchanting jungles, rich farm land, stretches of desert, and of course, white sand beaches and turquoise sea, Big Island offers unrivaled natural beauty no matter where you reserve your private vacation home. Guests seeking oceanfront luxury villa rentals on Big Island will find no shortage of beaches located nearby private vacation homes. Affluent travelers often enjoy launching their vacation on Hapuna Beach, famed for its sugary white sands and sparkling turquoise sea waters. Punalu’u offers volcanic-tinged black sands, while Papakōlea features mesmerizing green sand shorelines colored from ancient lava flows.

Oahu is a famous Hawaiian island vacation destination for affluent travelers seeking extravagant private vacation homes bathed beneath the light of a boundless summertime climate. Visitors to Oahu will find the island chock-full of world-famous snorkeling sites, renowned nightlife scenes, white sand beaches, and cultural adventures. As home to Honolulu, the island attracts discerning travelers seeking a taste of Hawaii’s bustling epicenter – many guests will book luxury villa rentals here for a business retreat or a holiday filled with cultural daytime activities.  Head south to Waikiki for a more traditional seaside getaway, where a famous expansive of golden sand beaches, extravagant spas and resorts, and private vacation homes offer the ultimate luxury vacation experience for travelers to Hawaii. Oahu also features numerous historic sites worth exploring, including the USS Arizona Memorial, the National Memorial Cemetery of the Pacific, the Valley of the Temples Memorial Park, and Pearl Harbor.

The island of Kauai attracts affluent travelers seeking the perfect combination of relaxed seaside living and otherworldly natural beauty. An idyllic vacation destination for honeymooners or couples celebrating their anniversary, it’s difficult to find an island topography as enchanting as Kauai landscape. Gleaming white sand beaches, turquoise sea, majestic mountain peaks and cascading waterfalls all converge to offer a sublime version of paradise. Head to Hanalei Bay on Kauai’s North Shore, where luxury villa rentals are surrounded by guava trees, ocean waters, and unspoiled natural scenery. While here, stop by the Ha’ena State Park – an ideal daytime activity for family-friendly retreat and nature enthusiasts. Guests who book private vacation homes on the island’s South Shore will find a slew of aquatic daytime activities here, from world-class snorkeling sites and scuba diving launch pads to famous surf breaks.

Whether you choose oceanfront luxury villa rentals in Maui or Kauai, or the extravagant private vacation homes nearby downtown Honolulu, the state of Hawaii is synonymous with a luxury vacation experience. Select from Villaway’s luxury villa rentals on a Hawaiian Island today, and start preparing for a dream tropical getaway.