Distinctive luxury properties for the ultimate trip
Distinctive luxury properties for the ultimate trip
Start-to-finish trip planning
Concierge teams coordinate your arrival, departure, and everything in between.
300+ point inspection
Every Luxury Retreats home is personally verified to be in pristine condition.
On-trip care, 24/7
Premium, on-demand assistance for any question, at any time of day.
259 luxury villas and vacation rentals in Hawaii
1 – 16 of 259 Rentals
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How to Enjoy your Hawaii Vacation to the Fullest
Fiery sunsets, tropical cocktails and sapphire-blue waters that stretch out as far as the eye can see… there’s no denying that Hawaii is a magical place. Where else in the world can you watch molten red lava hitting the surface of the ocean in clouds of steam? Whether you’re a creature of leisure or an adventurer, you won’t run out of things to do and places to discover when vacationing on one of Hawaii’s beautiful islands.
Reach new heights
Hawaii is a dream comes true for travelers who enjoy a challenge, and motivated hikers will see their efforts well rewarded. Make your way to Mount Haleakala in Maui at just the right time of day, and you’ll catch the sun setting on a breathtaking volcanic landscape. Or hop in your care and drive along the Road to Hana for scenic views and plenty of photo-ops.
One of the most beautiful (and dangerous) hikes in the world, the Kalalau Trail on Kauai island promises a heart-racing experience. Those willing to live life on the edge will come home from their trip with thrilling tales of wild encounters and hazardous climbs. Take note - this adventure is for experienced hikers only. Newbies or parents travelling with kids will find family-friendly trails at Waimea Canyon national park.
Vacationers who want to witness Hawaii’s awesome natural wonders will be blown away by Kilauea on Big Island. We highly recommend you take a helicopter tour to soar above Hawaii’s most active volcano, a once-in-a-lifetime experience you’ll never forget. Other unique activities on Big Island include visiting Mauna Kea’s snowy summit and the more family-friendly hike to Wailuku River State Park’s Rainbow Falls.
Make a splash
If you’ve ever dreamed of riding waves, your Hawaii vacation is the perfect moment to start! Beginner surfers will be able to choose from a variety of surf schools or one-on-one instructors on Hanalei Beach in Kauai. Advanced surfers will find many challenging waves to ride on every island, including legendary surf-sites like Maui’s Jaws, and Oahu’s Waimea Bay and legendary North Shore.
From deep-sea fishing to snorkeling adventures and romantic sunset cruises, there is more than one way to earn your sea legs in Hawaii. From September to March you might be lucky enough to catch a glimpse of humpback whales frolicking along Maui’s shores. Feel safer on dry land? These gentle giants are sometimes visible from the beach!
If you’re a self-proclaimed beach bum, you’re in for a treat! There is no shortage of long stretches of sandy beaches - of every color - and unspoiled secret coves in Hawaii. On Big Island’s green sand beach at Papakolea, you’ll witness the beauty of golden-green sands and turquoise waters contrasting with ocean carved volcanic cliffs. Or make your way to Punalu’u black sand beach, where you have a good chance of witnessing Hawksbill and Green turtles basking in the sun.
Book some Tee Time
With over 70 courses strewn across its 6 islands, Hawaii is one of the world’s golf capitals.
Hawaii’s golf courses are internationally praised for their beauty and imaginative landscaping. Pros travelling to Big Island will enjoy practicing their favorite sport on the Kohala Coast’s many golf clubs and resorts, while amateurs can try their hand at a new hobby on one of the many independant courses across the island.
Golf enthusiasts travelling to Maui are in for a truly spectacular experience at the Wailea resorts in the wake of mount Haleakala, surrounded by truly breathtaking views. On Kauai, and Oahu, Golfers can experience practicing their favorite sport while hearing the Ocean lap at the island’s rugged shores, as fairways weave through lush vegetation and are lined with spectacular cliffs.
Experiencing beachfront vacation rentals in Hawaii
A stay in one of ourKauai beach villas means waking up to spectacular views, and relaxing by your infinity pool after a day of horseback riding through Hanalei Wildlife refuge or kayaking on the Hanalei river. Lovers of the great outdoors will enjoy how close to secret beach coves and Na’Aina Kai Botanical Gardens our Kauai homes are, while golf enthusiasts can choose a villa that is a short drive from the world-class Makai Golf Club at Princeville.
Wake up with the sunrise and admire an endless stretch of turquoise blue water and lush green mountains in one of our Maui vacation rentals . With sprawling terraces, gorgeously designed infinity pools and tropical inspired grottos, your Maui villa is the perfect place to relax after a day of adventures on land and sea.
Our Oahu vacation rentals are some of the most lavish in Hawaii. Foodies and night owls will enjoy our modern beachfront flats in Honolulu, a city known for its imaginative cosmopolitan restaurants and fantastic shopping. Sushi lovers in particular will love the fusion of Hawaiian, Japanese and American cuisines. If you’re traveling with a big group, you might want to consider throwing a private luau at your Oahu villa, complete with poolside tropical cocktails and a delicious Hawaiian BBQ.
Feeling inspired? Just fill in your details in the form above, and one of our Villa Specialists will get in touch with you to help you find a Hawaii villa that’s right for you and your group.