Home » Vacation Rentals

Vacation Rentals

Hawaii’s Most Luxurious Vacations Rentals

Maui:

Kai Ala Beachfront estate in Kaanapali Hawaii
Average $13,000/night

1. Kai Ala

Kaanapali, Hawaii

This exquisite eleven thousand square foot Luxury Vacation home, on nearly a full private acre, and located directly on Kaanapali Beach is hotel-zoned as a beach-front luxury vacation home. Perfect for entertaining large groups of people with its 8 bedrooms and 9.5 baths…

10 Beds

9.5 Baths

8 Bedrooms

Average $8,380/night

2. Garden Villa

Kaanapali, Hawaii

This 12 bedroom gem combines all four villas in building 2 of the Luana Garden Villas. 2 adjacent grounded villas and the 2 adjacent elevated villas directly above boast a combined 8000 sq ft of interior living area, perfect for that large special gathering…

12 Beds

14 Baths

12 Bedrooms

Average $8,345/night

3. Lipoa Kahakai

Kihei, Hawaii

The courtyard is completely private, exclusive for the guests of Aloha Villas Resort. There is gated parking with 8 parking spaces, electronic gates to enter the courtyard, and surveillance cameras for your safety and security. Within the courtyard is a heated saltwater…

12 Beds

14 Baths

12 Bedrooms

Average $5,785/night

4. Luana Garden

Kaanapali, Hawaii

This luxurious 9 bedroom gem combines two neighboring ground villas with an elevated neighbor directly above to create over 6000 sq ft of interior living area, perfectly suited to larger groups or families. Since you will be staying within the 38 beachfront acres…

9 Beds

9 Baths

9 Bedrooms

Average $5,785/night

5. Honua Kai Resort

Kaanapali, Hawaii

Enjoy an effortless vacation with footstep access to Enclave Three’s pool, hot tub, and fire pit area, as well as a convenient location in very close proximity to the greater Honua Kai Resort amenities including the Hokulani deli, Duke’s Beach House…

9 Beds

9 Baths

9 Bedrooms

Average $5,753/night

6. Kapalua Bay Villa

Kapalua, Hawaii

With over 2700 square feet of indoor living space and an additional 628 sq. ft. of outdoor relaxation, this villa will comfortably entertain a large gathering. Exotic hardwoods gleam in the sunshine streaming through the full-length windows and Nano doors and reflect…

3 Beds

3 Baths

3 Bedrooms

Average $5,585/night

7. Honua Garden

Kaanapali, Hawaii

Enjoy an effortless vacation with footstep access to Enclave Three’s pool, hot tub, and fire pit area, as well as a convenient location in very close proximity to the greater Honua Kai Resort amenities including the Hokulani deli, Duke’s Beach House…

9 Beds

9 Baths

9 Bedrooms

Average $5,585/night

8. Makena Garden

Makena, Hawaii

Makena Garden Estate is an upscale contemporary-styled 4,800 square foot 4.5 bedroom (King, King, King, Queen) 4 bath virtual oceanfront home with spectacular panoramic ocean views in the leeward sunnier Makena area on Maui Island…

9 Beds

9 Baths

9 Bedrooms

Average $5,570/night

9. Maui Baby Beach

Lahaina, Hawaii

This is ‘Your Own Private Paradise’ on Maui. There is an additional studio villa with a full Kitchen and Bath. Recently installed is a new multi-zone air conditioning and cooling system for your use to keep you comfortable while you gaze out the 180-degree oc…

5 Beds

5 Baths

4 Bedrooms

Average $5,570/night

10. Kapalua Ikena

Kapalua, Hawaii

Explore the beautiful artwork, vaulted ceilings, custom woodwork, and openness to the outdoors. Custom-built cabinetry and stainless steel appliances compliment the large granite island with seating. The separate dining room opens onto the lanai with Nano doors…

5 Beds

5 Baths

4 Bedrooms

Average $5,328/night

11. Lahaina Moana

Lahaina, Hawaii

Welcome to Maui’s most desirable vacation home! Your own private mansion on the water in Lahaina (this home is partial oceanfront). This is currently the largest vacation rental in Hawaii in terms of both square footage and sleeping arrangements…

4 Beds

5 Baths

8 Bedrooms

Average $5,328/night

12. Maui Kukuna

Spreckelsville, Maui

This private estate is spread over 2 ½ acres of prime beachfront in exclusive Spreckelsville, Maui, HI, containing stately palms, a variety of bamboos, and lush tropical plants. This gated property offers a secluded and protected launching beach, and spacious…

4 Beds

5 Baths

8 Bedrooms

Average $3,799/night

13. Pacific View

Lahaina, Hawaii

Pacific View is nestled in the majestic West Maui Mountains, a vast area of lush valleys and steep cliffs. This lovely 5-acre estate is uniquely situated to capture all of the beautiful west Maui offers, yet just a short drive to the heart of historic Lahaina town…

8 Beds

5 Baths

6 Bedrooms

Average $3,000/night

14. Maui Kukuna

Lahaina, Hawaii

We invite you to unwind at Paradise Cove, an oceanfront property located in Napili on the stunningly beautiful West shore of Maui. You, your family, and friends are sure to be pleased with this 3 bedroom plus office, 4.5 bathroom home, complete…

3 Beds

3.5 Baths

3 Bedrooms

Average $2,700/night

15. Garuda Estate

Lahaina, Hawaii

We invite you to indulge in this magnificent 3,300 square foot villa nestled on the southwest shore of Maui. From the moment you arrive at the statue flanked entry, you’ll be in awe with views of the majestic blue ocean, and the Island of Lana’i in the distance…

3 Beds

3 Baths

3 Bedrooms

Oahu:

Average $15,291/night

Waikiki Kaona

Waikiki, Hawaii

Wake up in the heart of Waikiki at a fully furnished 1,700 square foot penthouse condo designed to satisfy your every need & desire. You won’t find anything like this similar in all of Waikiki. This “Close to Everything with Everything” & all the bells and whistles listing…

10 Beds

2 Baths

3 Bedrooms

Average $11,000/night

Kailua Cabana

Kailua, Hawaii

Relax and unwind at this stunning estate with direct access to the beautiful sandy beaches of Kailua. This exquisite 5 bedroom main residence offers 11,000+ sq ft of lavish living plus a gorgeous separate 3 bedroom guest house. Incredible details, expert craftsmanship…

8 Beds

8 Baths

8 Bedrooms

Average $10,893/night

Banyan Ohana

Kahala, Hawaii

Banyan Ohana is Oahu’s most luxurious vacation rental near the foot of Diamond Head. The exquisite home features seven bedrooms, eight full baths, and a half-bath, encompassing 14,000 square feet all within a private beachfront estate. This stylish and…

8 Beds

9 Baths

8 Bedrooms

Average $10,700/night

Kahala Hale

Honolulu, Hawaii

Boasting an extraordinary beachfront location, this private Kahala vacation rental estate provides all the modern luxury features your large group requires, with the charm of old Hawaii. Kahala Beachside Estate offers direct beach access, its own pool, and spa, seven…

14 Beds

8 Baths

7 Bedrooms

Average $10,000/night

Kailua Kahakai

Kailua, Hawaii

These two magnificent homes both sleep 12 people (24 total) is nestled on two acres of land, that has its own shared swimming pool and hot tub, and the most beautiful sandy beach imaginable at your doorstep. It is completely furnished and beautifully maintained…

12 Beds

12 Baths

12 Bedrooms

Average $10,000/night

Waimanalo Hale

Waimanalo, Hawaii

Experience Hawaii in an exquisite beachfront mansion with panoramic ocean views on beautiful Waimanalo Beach (famous filming locale for Magnum P.I., Hawaii 5-0, & Lost). Waimanalo’s small town doesn’t allow hotels, making it the perfect getaway from the…

10 Beds

8 Baths

9 Bedrooms

Average $8,286/night

One Kea Estate

Honolulu, Hawaii

Oahu’s Newest Luxury EstateOcean House is the newest residence in the collection of ultra-luxury homes designed by renowned Hawaii Architect Jim McPeak and built by San Diego based developer Mark Gosselin. This estate is a modern take on Oahu’s well-known…

6 Beds

7 Baths

6 Bedrooms

Average $6,970/night

Pipeline Hale

Pupukea, Hawaii

The Pipeline Manor is a spectacular example of modern island style. Unparalleled ocean views are available from multiple locations in the home bringing in the sights and smells of the Pacific. Other features include HDTV, gourmet kitchen, off-street parking…

5 Beds

4 Baths

5 Bedrooms

Average $6,400/night

Moanas Edge

Honolulu, Hawaii

The Jewel of Waikiki challenges traditional luxury with nine multi-room suites, each occupying an entire floor and offering complete privacy. The experience is enhanced with butler service, ensuring all requests are addressed promptly and discretely through…

3 Beds

4 Baths

4 Bedrooms

Average $6,339/night

Waikiki Ikena

Waikiki, Hawaii

Located in the rapidly growing urban neighborhood of Kaka’ako on the south shore of O’ahu, Hokua Grand Penthouse sits at the top of the luxury Hokua condominium, just across the street from Ala Moana Beach Park. With sensational ocean and city views…

4 Beds

4 Baths

3 Bedrooms

Average $5,500/night

Kea Moana

Lanikai, Hawaii

This gorgeous 5 bedroom, 4.5 bathroom, the gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful…

7 Beds

5 Baths

5 Bedrooms

Average $3,716/night

Kai Valhalla

Lanikai, Hawaii

With a private, gated entrance and a sophisticated and luxurious feel throughout, Kai Valhalla is the indulgence you need on your next Hawaiian vacation. This larger-than-life custom-built five-bedroom, four-and-a-half-bath home spread out over three stories is ideal…

6 Beds

5 Baths

5 Bedrooms

Kauai:

Average $7,143/night

Hanalei Kuono

Hanalei, Hawaii

Situated on over an acre of beachfront land, directly in the center of Hanalei Bay is this well-appointed five-bedroom gated estate, perfect for corporate retreats, extended families, or anyone else requiring privacy in the ultimate setting…

5 Beds

4 Baths

5 Bedrooms

Average $6,229/night

Oioina Estate

Kalihiwai, Hawaii

Between the mystical mountains and renowned Secret Beach, The Dali Hale Estate is more than a home: you’ll feel the magic the moment you arrive. With more than 500 feet of ocean frontage, the Dali Hale is the perfect place to gather for grand family reunions…

8 Beds

8 Baths

8 Bedrooms

Average $5,500/night

Lagoon Resort

Lihue, Hawaii

Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their…

3 Beds

2 Baths

2 Bedrooms

Average $4,200/night

Poipu Beach Hale

Koloa, Hawaii

An irresistible fusion of glamorous seaside resort and casually elegant, island-style private home, Waiohai Beach House offers the best of both worlds and more. The spacious, beautifully furnished 4BR/4BA villa (the only single-family vacation rental on Poipu Beach)…

4 Beds

4 Baths

4 Bedrooms

Average $4,000/night

Heavenly Ohana

Hanalei, Hawaii

Located beachfront on the enchanting Hanalei Bay, Lani Kai (“Heavenly Ocean Home”) is a newly remodeled four bedroom, three bathroom home ideal for a large family or couples traveling together wanting some well-deserved space. Recent renovations include…

4 Beds

3 Baths

4 Bedrooms

Average $3,869/night

Pali Kai

Lihue, Hawaii

The pristine ambiance of the Pali Kai Palace is accentuated by its extraordinary vista. Perched upon the Kalapaki Cliffs, this unique location in Lihue offers sensational views of the ocean, mountains, and harbor. With intentional interior designing and custom…

8 Beds

7 Baths

7 Bedrooms

Average $3,801/night

Haena Beach House

Haena, Hawaii

Haena Beach House offers a once-in-a-lifetime vacation experience, providing contemporary luxury in a private beachfront setting. Ideal for large groups, the home showcases breathtaking panoramic views of the Pacific from its living spaces and each of its bedrooms…

6 Beds

5 Baths

5 Bedrooms

Average $3,627/night

Hale Mana

Kalihiwai, Hawaii

Welcome to Hale Mana, one of Kauai’s most beautiful island treasures. This stunning three-acre private estate will bathe you in every luxury with its beautifully appointed amenities, secluded beach, and tremendous ocean views. If you are looking for Hawaii’s best…

11 Beds

6 Baths

5 Bedrooms

Average $3,571/night

Dolphin House

Hanalei, Hawaii

Renovated and expanded in July 2011 to include 7 bedrooms! Hanalei’s classic property sits on over one acre of land. The largest oceanfront rental property in Hanalei Bay! The residence and guesthouse have been upgraded throughout. New finishes include…

8 Beds

7 Baths

6 Bedrooms

Average $3,566/night

Kumu Home

Lihue, Hawaii

Timbers Kauai – Ocean Club and Residences is a residential enclave located on the ocean*s edge of the Pacific. All of Timbers* signature amenities are here; such as two pools to fit whatever mood you are in – a serene two-tiered infinity pool overlooking…

4 Beds

3 Baths

3 Bedrooms

Average $3,495/night

Nanini Hale

Lihue, Hawaii

This private residence has an expansive floor plan and spacious lanais. Enjoy the sunrise over the Pacific Ocean and eastern views of the resort and the Nanini Point lighthouse. The split-level floor plan provides space for everyone to relax. The floor-to-ceiling…

2 Beds

1 Bath

5 Bedrooms

Average $3,200/night

Hanalei Cottage

Hanalei, Hawaii

Located on Kauai’s beautiful north shore, this beachfront home is surrounded by lush, tropical foliage. Enjoy a spacious living room upstairs as well as a comfortable family room downstairs. The upstairs balcony features magnificent views of Hanalei Bay which is just…

4 Beds

4 Baths

3 Bedrooms

Big Island

Average $4,684/night

Fairways North 1

Mauna Kea Resort, Hawaii

Nestled in seclusion on an acre of land in the exclusive Mauna Kea Resort, this five-bedroom, seven-bath estate home represents the epitome of luxury, leisure, and ease. Fairways North #1, ideal for families or groups of friends, consists of three pod-style…

4 Beds

3 Baths

3 Bedrooms

Average $4,600/night

Hapuna Beach Residence

Mauna Kea Resort, Hawaii

This incomparable, oceanfront, newly-constructed, ground-level penthouse offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a superb chef’s kitchen outfitted with professional-grade Wolf, Sub-Zero, and Miele appliances, wine storage…

2 Beds

1 Bath

5 Bedrooms

Average $4,540/night

Blue Lagoon

Puako, Hawaii

Enjoy the best Hawaii has to offer in this luxury 10,000 sq ft tropical estate. It includes a private heated pool/spa and includes access to Mauna Lani resort area amenities including a private beach and beach club(included with rental), tennis, and fitness…

4 Beds

4 Baths

3 Bedrooms

Average $4,496/night

Hapuna Beach Hale

Hapuna, Hawaii

This impeccable, oceanfront, newly-constructed, ground-level island masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a true chef’s kitchen outfitted with professional-grade Wolf, Sub-Zero, and Miele appliances, wine…

4 Beds

4 Baths

4 Bedrooms

Average $4,482/night

Beach House at the Bluffs

Mauna Kea Resort, Hawaii

Built in 2008 by architect Roth Kimura, this two-story, 8,000 square foot luxury estate home with 2,750 square feet of outdoor entertaining space is located on a private, secure cul-de-sac in the Bluffs area of the Kohala Coast. The Beach House at the Bluffs…

6 Beds

7 Bath

4 Bedrooms

Average $4,282/night

106 Pu’u Kole

Kaupulehu, Hawaii

This resort home cradles its guests in the lap of sumptuous serenity. Situated on a premier private corner lot overlooking the 13th green of the exclusive Ke‘olu golf course, this home boasts over 4,200 square feet of interior living space and 1,500 square feet…

5 Beds

5 Baths

4 Bedrooms

Average $4,208/night

Kulanakauhale 3558

Kailua-Kona, Hawaii

Set on a bluff in the newest residential community at the exclusive Four Seasons Resort Hualalai, this luxury ocean-view estate home provides the ideal setting for a family or friend’s getaway to paradise. The home boasts over 3,460 square feet of interior space…

4 Beds

5 Baths

4 Bedrooms

Average $4,200/night

Pauoa Enclave

Puako, Hawaii

Located in a prime position, within the gated, luxury enclave of Pauoa Beach, in the Big Island’s Mauna Lani Resort, the Pauoa Beach Oceanfront Villa delivers a 5-star vacation rental experience. Travelers seeking elegant surroundings, access to private clubs…

5 Beds

4 Bath

4 Bedrooms

Average $4,009/night

Seaside Estate

Holualoa, Hawaii

Transcend paradise with our absolute oceanfront 3 story 5 bedroom home located only blocks from Kailua-Kona town and within a guarded gate community of luxury estates. Your private oceanfront setting overlooks rich lava, white sands, crashing waves, and Hawaii’s…

5 Beds

7 Baths

5 Bedrooms

Average $4,000/night

Laueki Estate

Kaupulehu, Hawaii

Centrally located in this tranquil and rejuvenating oceanside retreat, Lalani Lau’eki is a private oasis nestled between the exquisite and expansive ocean and mountain views. Just a short golf cart ride away is everything the premier resort offers such as world…

4 Beds

5 Baths

4 Bedrooms

Average $3,977/night

Pakui Retreat

Kaupulehu, Hawaii

Welcome to your very own corner of paradise at Hualalai Four Seasons Resort! This estate is your perfect home-away-from-home. Highlighting Hawaii’s natural beauty with indoor-outdoor living, the Pakui Retreat estate features exquisite interior ambiance…

5 Beds

4 Bath

3 Bedrooms

Average $3,867/night

Pauoa Beach Villa

Puako, Hawaii

Pauoa Beach Estate has been meticulously cared for, and designed specifically to live life relaxed while enjoying designer furnishings and elegant island sophistication. Exquisite and rich Koa and Sapele wood millwork pays homage to the home’s location…

5 Beds

6 Baths

4 Bedrooms