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Island of Maui

Maui Luxury Rentals

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Luxury on Maui means space, privacy and a view you can't stop looking at. We chose these rentals one by one: the condos at Maui's three flagship resorts, only the best units at the next tier, and Maui's finest estate homes.

Rentals chosen unit by unitVilla or hotel, comparedEvery view checkedOnly legally licensed rentals

On Maui, price alone doesn't buy luxury. Sort the island's rentals by price and you mostly get size: big units in good buildings, and large houses. Our luxury list hand selected. First, every residence at Maui's three flagship resorts that define luxury in Hawaii. Next, stand-out units at great complexes, and finally, the finest estate homes from Maui's very limited vacation home inventory. That's fewer than one in 35 of the Maui rentals we list.

Villa or five-star hotel? A villa gives you room to spread out, a full kitchen, laundry and a lanai of your own - often for less per person when you travel as a family or group. A hotel gives you daily housekeeping, room service and a kids' club. The Resort at Kapalua Bay blurs the line with private residences inside a full resort, and Wailea Beach Villas and Ho'olei sit beside Wailea's five-star hotels.

Find yours by party size: for two (one and two bedrooms) · for a family (three bedrooms) · for the whole clan (four or more).

Maui's Luxury Rentals
1 in 37
Maui rentals we list make our luxury list
21 of 346
Honua Kai units make the cut
2x
as many reviews celebrate the spaciousness of our luxury picks
5x
more reviews highlight family reunions, where splurging makes memories

Source: 3,538 guest reviews of our 120 Maui luxury picks and 135,322 of the island's other rentals, 2022 to 2026 (October 2026).

How we choose: Three resorts on Maui are exemplars of luxury and every residence there makes our list. At Maui's next tier a unit must be rated 4.9+ by at least 10 guests, have a verified ocean view and be priced like the building's best to even be considered. Estate homes need air conditioning, a pool or the ocean out front, and a 4.8+ rating from at least 10 guests to be considered. A subset make the final list.

01The top tierTier 1 of 3

Three resorts on a level of their own: gated collections of large, privately owned residences with five-star neighbors. Every rental we list in them makes our luxury list.

The Resort at Kapalua Bay aerial photo1 4.96Above Kapalua Bay

The Resort at Kapalua Bay

All 11 rentals make our luxury list · avg $5309/nt

The former Montage: three- and four-bedroom residences built like luxury homes, with the full resort around them - a multi-level oceanfront pool, spa and restaurants. Kapalua Bay is a short walk; Marriott now runs it ahead of a planned St. Regis conversion.

Wailea Beach Villas aerial photo2 4.94On Wailea Beach

Wailea Beach Villas

All 30 rentals make our luxury list · avg $2005/nt

Two- to four-bedroom villas of 1,900 to 3,100 sq ft right on Wailea Beach, between the Shops at Wailea and the beach walk. Beach attendants, an adults-only oceanfront infinity pool and a family pool; select villas have private plunge pools.

Hoolei aerial photo3 4.94Across from the Four Seasons

Hoolei

25 of 27 rentals make our luxury list · avg $1492/nt

Maui's lowest-density resort, about four villas an acre, across the road from the Grand Wailea and Four Seasons. Big multi-bedroom villas with en-suite baths and ocean-view lanais, around a pool with a waterfall, grotto and sandy kids' beach.

02The next tier: only the best unitsTier 2 of 3

Excellent resorts where not every unit is luxurious, so we picked units, not buildings: the ones guests rate 4.9 or higher, with a verified ocean view, priced like the building's best. Each card counts how many make the cut.

Kapalua Bay Villas aerial photo4 4.83Above Oneloa Bay

Kapalua Bay Villas

4 of 71 rentals make our luxury list · avg $1086/nt

Sixteen oceanfront acres above Oneloa Bay with three heated pools, the Kapalua Coastal Trail at the edge and Kapalua Bay a short walk away. One- and two-bedroom villas with central AC, looking across the channel to Molokai.

Honua Kai Resort aerial photo5 4.86North Kaanapali Beach

Honua Kai Resort

21 of 345 rentals make our luxury list · avg $2196/nt

Maui's biggest condo resort, on North Kaanapali Beach: a lazy river, kids' pool with a slide and a quiet adult pool, Duke's Beach House and a market on site, and a shoreline walk to Whalers Village. Units vary widely, so only its best make our list.

Kaanapali Alii aerial photo6 4.81On Kaanapali Beach

Kaanapali Alii

6 of 30 rentals make our luxury list · avg $1440/nt

Run like a hotel, right on Kaanapali Beach and a walk from Whalers Village and Black Rock: a 24-hour front desk, a quiet adult pool and a kids' pool, tennis and a beach activities center. Large units with full kitchens and in-unit laundry.

Polo Beach Club aerial photo7 4.83On Polo Beach

Polo Beach Club

7 of 22 rentals make our luxury list · avg $1339/nt

Eight stories on quiet Polo Beach at the south end of the Wailea Beach Walk, with an oceanfront pool and hot tub. Units run 1,200 to 1,300 sq ft; the south-facing and oceanfront ones have the best views.

Makena Surf aerial photo8 4.88On Paipu Beach, Makena

Makena Surf

4 of 25 rentals make our luxury list · avg $1125/nt

A gated, low-density resort on secluded Paipu Beach, beyond Wailea's crowds: two pools, two hot tubs, tennis and snorkeling off the shore, with turtles a near-daily sight. Big units, nearly all with verified ocean views.

03Estate homesTier 3 of 3

Private homes for the whole group: top-rated, air-conditioned, and each with a pool or the ocean out front, from Kapalua to Makena.

Maui luxury estate homes

13 homes · avg $3618/nt · 7 oceanfront · 4.95 avg rating

Room for everyone. Our estate picks average more than four bedrooms, every one has a pool, and more than half sit right on the ocean.

Expect from about $2,000 a night, and more for oceanfront.

Maui Luxury Resorts Map

The numbered pins match the cards above; tap one for details.

The Entire Luxury Collection

Every Maui luxury pick, ranked by reviews

All three tiers in one list, ranked by review quality. Use the Search Filters button to do a vacancy search or narrow by bedrooms, price, beachfront or oceanfront.

$1755/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKKQT (sleeps 8)
5 (216 reviews)
Luxury 3BR ocean-front condo in Honua Kai Resort, Maui. Professionally decorated with custom furnishings, beachfront views, and lanai with outdoor kitchen.
$1553/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKXK (sleeps 8)
5 (204 reviews)
Luxurious 3BR/3BA Honua Kai Resort condo on 5th floor with ocean views from every room. Gourmet kitchen, beach gear, 4 pools, and on-site dining.
$1530/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KTQT (sleeps 8)
5 (186 reviews)
Luxury 3-bedroom, 3-bath, 2500 sq. ft. Penthouse Villa J205 at Wailea Beach Villas with ocean views, gourmet kitchen, and resort amenities.
$1475/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KQX (sleeps 10)
5 (173 reviews)
Luxurious 3 bed, 3.5 bath townhome at Hoolei Wailea Beach with private elevator, ocean views, BBQ area, entertainment system, and resort amenities.
$1632/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KXKQ (sleeps 10)
5 (167 reviews)
Luxury 3BR condo at Honua Kai Resort, Maui's only beachfront condo in 30 yrs. Gourmet kitchen, luxury linens, 3 beachside pools, Dukes Restaurant. Direct ocean views from every window.
$1301/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKTQX (sleeps 6)
5 (162 reviews)
The Maui Escape is a luxurious 2.5 bedroom, 2 bathroom villa with 2,200 sq ft of living space. It has views of the upper pool, a private lanai, and offers unique appointments such as custom wood shutters, granite and hard wood finishes, and honed marble floors.
$1021/nt (avg.)
Location: Makena Surf , Makena
Bedrooms: 2 - KK (sleeps 6)
5 (161 reviews)
Stunning ocean views, 2 bedrooms with ensuite bathrooms, large lanai with lounge chairs and dining table, gourmet kitchen, TV/den area, and laundry room.
$1171/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKKX (sleeps 8)
5 (160 reviews)
Deluxe Ocean View villa in the top row 'A' building with unobstructed panoramic views of the ocean. Private elevator, gourmet kitchen, and outdoor BBQ. Nearby amenities include restaurants, golf courses, shopping, and white sand beaches.
Location: Hoolei , Wailea
Bedrooms: 3 - KKQ (sleeps 8)
5 (152 reviews)
Maui Breeze Retreat at Ho'olei is a luxurious 3 bedroom, 3.5 bath townhome with stunning Pacific Ocean views. Amenities include a swimming pool, hot tubs, sauna, fitness facility, private elevator, and gourmet kitchen.
$2133/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 4 - KKQK (sleeps 8)
5 (140 reviews)
Beachfront penthouse with panoramic ocean views, 4 bedrooms, 3 baths, complete 2017-2018 renovation, sleeps 8, direct elevator access, on-site amenities.
$1442/nt (avg.)
Location: Kaanapali Alii , Kaanapali
Bedrooms: 2 - FXK (sleeps 6)
5 (138 reviews)
Luxury, premier direct oceanfront 2 bed, 2 bath condo in Kaanapali Alii Resort. Max 6 guests, 1900 sq ft, smart TVs, Keurig coffee, beach towels/chairs, fitness room, spa, tennis courts, Lanai with seating and table/chairs.
Location: Lahaina
Bedrooms: 6 - KKFKQQ (sleeps 16)
4.9 (177 reviews)
Luxury 6BR/6BA estate on a private cul-de-sac amidst Royal golf course with ocean views. Pool, spa, BBQ, game room, A/C, walk to beach & restaurants.
Location: Lahaina
Bedrooms: 6 - KKTKK (sleeps 14)
5 (123 reviews)
Kahana Nui Villa is a 6-bedroom luxury oceanfront vacation rental home in Maui with stunning views, beach access, pool, hot tub, and unique Bali-inspired architecture.
$1090/nt (avg.)
Location: Makena Surf , Makena
Bedrooms: 2 - KK (sleeps 5)
5 (121 reviews)
Beachfront top floor condo with modern interior, spectacular ocean view, and access to Maui's best snorkeling. Luxuries include pool, hot tub, tennis courts, and activity locker. Fully equipped kitchen and entertainment center. Sleeps up to four adults.
$3409/nt (avg.)
Location: Kihei
Bedrooms: 4 - KKKK (sleeps 10)
5 (118 reviews)
One-of-a-Kind Maui Getaway with infinity pool, traditional/modern design, tropical views, whale watching, and stargazing. Experience the Aloha!
$1110/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 4 - KTQXKK (sleeps 9)
5 (116 reviews)
Luxury 4BR Maui condo with panoramic ocean views, gourmet kitchen, Baby Grand piano, 75" smart TV, fitness center, 2 pool/spas, and underground parking. Located between The Grand Wailea & The Shops at Wailea with excellent shopping and dining options.
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KTT (sleeps 8)
5 (110 reviews)
Luxury 3BR/3BA penthouse in Wailea with a large lanai, BBQ, gourmet kitchen, and access to pools, beach, fitness center, and concierge service.
$4855/nt (avg.)
Location: Lahaina
Bedrooms: 5 - KKKQQ (sleeps 10)
5 (105 reviews)
Stunning U-shaped beachfront home in Maui with 5 bedrooms, each with an en suite bath and lanai. Features a pool, spa, fully equipped kitchen, and direct beach access. Enjoy snorkeling, surfing, and watching sea turtles.
$940/nt (avg.)
Location: Makena Surf , Makena
Bedrooms: 2 - KT (sleeps 4)
5 (103 reviews)
Beachfront 2BR/2BA condo with panoramic views, pool, hot tub, tennis courts, herb garden, and outdoor grill. Luxurious and newly remodeled.
$1092/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 2 - KK (sleeps 4)
5 (94 reviews)
Experience paradise in this updated oceanfront condo at Polo Beach Club! Enjoy breathtaking views, steps from the beach, and access to private pool and BBQ.
$1449/nt (avg.)
Location: Makena Surf , Makena
Bedrooms: 2 - KT (sleeps 4)
5 (92 reviews)
Luxury condo with stunning views, fully remodeled with high-end finishes, accommodating 4 guests. Steps away from the beach, with pools, jacuzzis, tennis courts, fitness center, and free parking. Fully air-conditioned with Sonos sound system and flat-screen TVs.
Location: Hoolei , Wailea
Bedrooms: 3 - KQQQQQ (sleeps 8)
5 (87 reviews)
Spacious townhome with ocean views in Hoolei community. Features cherry cabinets, limestone flooring, premium appliances, and built-in BBQ. Amenities include pool, gym, and 24-hour security. Close to upscale shopping and dining.
$2604/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 2 - KXT (sleeps 6)
5 (85 reviews)
Wailea Beach Villas offers a luxurious 2 bedroom + den/2 bath penthouse villa with a private elevator, BBQ, and ocean views. Amenities include pools, hot tubs, fitness center, and beach attendants. Located near golf courses, spas, and upscale shopping/dining.
$1610/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 4 - KXKQ (sleeps 8)
4.9 (114 reviews)
Newly renovated townhouse-style villa with 4 private bedrooms, 3.5 bathrooms, vaulted ceilings, Italian cabinetry, and a secure garage. Closest to the pool and beach, with a semi-private backyard. Features a 5-star pool, sauna, and waterfall.
$1955/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKQT (sleeps 7)
5 (84 reviews)
Luxurious Beachfront Penthouse with panoramic ocean views, gourmet kitchen, Viking grill, infinity pool, spa, concierge, fitness center, and more!
Location: Hoolei , Wailea
Bedrooms: 3 - XKQK (sleeps 10)
5 (81 reviews)
Luxury 3BR/3.5BA condo near the beach with breathtaking views. Private elevator, gourmet kitchen, lanai with BBQ, and pool with waterfall. Sleeps up to 10.
$915/nt (avg.)
Location: Kapalua Bay Villas , Kapalua
Bedrooms: 2 - KKX (sleeps 6)
5 (80 reviews)
Hale O Ho'okipa is a luxurious oceanfront villa in Kapalua Bay with custom furnishings and high-end art. It includes amenities such as central AC, secured wifi, and beach gear. No hidden fees.
$1239/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KK (sleeps 8)
5 (78 reviews)
Luxury 3BR villa in Hawaii's #1 resort, with ocean views, gourmet kitchen, private lanai, pool, jacuzzis, fitness center, and beach access.
$1249/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKKX (sleeps 8)
5 (75 reviews)
3BR 3.5BA Royal Penthouse in Honua Kai Resort on 10th floor with panoramic ocean views, wrap-around lanai, full Viking kitchen, and beach gear provided. Sleeps up to 8.
$1276/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 2 - XQK (sleeps 5)
4.9 (100 reviews)
"Relax in style at Polo Beach Club! Updated 2 bed/2 bath with private lanai and ocean views. Steps from Polo Beach and Wailea beach path. Beach gear included."
$3278/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKTX (sleeps 8)
5 (73 reviews)
Wailea Orchid Villa is a luxurious 3-bed penthouse with stunning Pacific Ocean views. It has a gourmet kitchen, marble floors, and sleeps up to 8.
$946/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 2 - KKX (sleeps 6)
5 (71 reviews)
Hokulani 709 at Honua Kai Resort is a 2-bed, 2.5-bath condo with stunning ocean views, wrap-around lanai with a private BBQ, and modern amenities.
$1408/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKK (sleeps 8)
4.9 (95 reviews)
Luxury 3BR condo in Honua Kai Resort, Maui. 9th floor with stunning views of Ka'anapali Beach, Lanai, and Molokai. Spacious lanai, new kitchen, and amenities. Access to pools, hot tubs, fitness center, and Duke's Restaurant. Walking distance to shopping and farmer's market.
$2718/nt (avg.)
Location: Lahaina
Bedrooms: 5 - KQXQQK (sleeps 14)
5 (70 reviews)
5 bedroom luxury home in Napili with ocean views of Molokai Island. Private backyard with hot tub, pool access, and beach cove just a 3-minute walk away. Well-stocked kitchen, two living areas, and comfortable furnishings.
$1059/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 2 - KQTX (sleeps 7)
5 (69 reviews)
Luxury 2nd floor penthouse at Wailea Beach Villas, #3 Resort in Hawaii. Beach access, high-end design, gourmet kitchen, private lanai w/ BBQ. King, Queen, Twin bed, convertible queen couch. Infinity pool, spa, fitness center on-site. Near shops & restaurants.
$1091/nt (avg.)
Location: Kaanapali Alii , Kaanapali
Bedrooms: 2 - QK (sleeps 6)
4.9 (89 reviews)
Luxury 2BR, 2BA oceanfront condo at Kaanapali Alii Resort, steps from Whalers Village, with top-notch amenities, stunning ocean views, and beach access.
Location: Kaanapali Alii , Kaanapali
Bedrooms: 3 - KKK (sleeps 8)
4.9 (89 reviews)
This 2-bed, 2-bath condo is located at Kaanapali Alii, a premiere resort on Kaanapali Beach. It has a fully equipped kitchen, flat-screen TV, and ocean views. Resort amenities include heated pools, whirlpool spas, tennis courts, and beach activities.
$1397/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - QKK (sleeps 8)
5 (64 reviews)
Luxury villa w/ ocean views, modern decor, spacious living, 3 ensuite bedrooms, private elevator, garage, pool, gym, and beach access in Maui.
$1363/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KFK (sleeps 8)
5 (64 reviews)
Luxury ocean-view villa on Maui, 3rd row at Ho'olei, with 3 bedrooms, ensuite configurations, private elevator, garage, Wolf grill, and Ho'olei pool access.
$1506/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KQK (sleeps 8)
5 (63 reviews)
2-level villa at Ho'olei Resort on Maui with stunning ocean views, 3 en-suite bedrooms, large gourmet kitchen, fully furnished lanais, and pool access. Walkable to the beach and shops at Wailea.
$1446/nt (avg.)
Location: Kaanapali Alii , Kaanapali
Bedrooms: 2 - KF (sleeps 4)
5 (63 reviews)
Luxury 2 bed/2 bath direct oceanfront condo in Kaanapali Alii Resort. Panoramic ocean views, gourmet kitchen, designer furnishings, and beach towels/chairs. Maximum of 4 guests. No daily maid service.
$1394/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKTTX (sleeps 8)
5 (61 reviews)
Luxury villa near top-rated Wailea beach with resort-style pool, fitness center, and ocean views. Gourmet kitchen, private lanai, and personal elevator.
$1569/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - QKX (sleeps 10)
4.9 (81 reviews)
Luxurious 3BR, 3.5BA villa in Wailea with resort oasis pool, 2 lanais, BBQ grill, AC throughout, beach gear, and walking distance to shops and restaurants.
$2084/nt (avg.)
Location: Haiku
Bedrooms: 5 - KKKTTQQ (sleeps 10)
5 (58 reviews)
Escape to Seaview in Upcountry Maui! This spacious home accommodates 10, offering stunning coastal views, a solar-heated pool, hot tub, and outdoor dining. Near top dining spots and beaches, it's a serene family retreat.
$1245/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKFF (sleeps 8)
4.9 (77 reviews)
Stunning ocean view villa in Hawaii's #1 resort. Top floor living area, elevator, pool table, indoor-outdoor living, 3 bedrooms, 3.5 baths, garage, beach/pool amenities, gated community.
$1210/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 3 - KQT (sleeps 5)
4.9 (77 reviews)
Escape to this tranquil oceanfront condo with stunning views, direct beach access, and a gourmet kitchen. Sleep comfortably in the private primary suite or guest room. Enjoy the pool, hot tub, and nearby dining and shopping.
$1756/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKK (sleeps 8)
4.9 (76 reviews)
Hokulani 929 at Honua Kai is a luxurious 3-bedroom deluxe ocean view suite with a spacious lanai, fully equipped kitchen, and stunning views.
Location: Lahaina
Bedrooms: 6 - KKKKKKK (sleeps 12)
4.8 (98 reviews)
Spectacular ocean views from upstairs lanai. 6 bedrooms, 5 bathrooms, large pool, game area, and bar. Gated property. Short walk to shopping plaza.
$707/nt (avg.)
Location: Kapalua Bay Villas , Kapalua
Bedrooms: 1 - XK (sleeps 4)
5 (53 reviews)
Luxurious Kapalua Bay Villa #37B1, fully remodeled in 2021. Scenic ocean view, 5-min walk to Kapalua Bay, Montage Resort, tennis, golf, hiking, zip-lining, several restaurants, and a first-class spa. Spacious, almost 1,000 sq. ft., one-bedroom, one bath.
$1434/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 2 - K (sleeps 4)
5 (52 reviews)
Prime luxury oceanfront Polo Beach Club penthouse with stunning views, designer furnishings, and gourmet kitchen.
$1010/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 2 - KKX (sleeps 6)
4.9 (70 reviews)
Luxury ground floor penthouse at Wailea Beach Villas, steps from pool. Gourmet kitchen, 2 primary bedrooms, den, lanai, 3 flat screens, 2 pools & spas. Adjacent to designer shops and restaurants. Adult-only beachfront infinity pool.
$2256/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 2 - KQQ (sleeps 6)
5 (51 reviews)
Oceanfront condo at Polo Beach Club 805. Direct beach access, amazing views, chic décor. Equipped kitchen, spacious living area, private lanai, central AC. Master bedroom with king bed, ensuite bath, ocean view. Guest room, 2 queen beds. Pool, jacuzzi, BBQ, herb garden on-site..
$4008/nt (avg.)
Location: Kihei
Bedrooms: 6 - KKKQQTT (sleeps 12)
5 (50 reviews)
Spacious 6BR, 5.5BA Maui beach house for 12 guests, with ocean views, saline solar-heated pool, and gourmet kitchen. Steps to the beach, close to shops and dining. Perfect for relaxing, paddleboarding, or surf lessons. Ideal island getaway!
$1192/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKDD (sleeps 8)
4.8 (89 reviews)
Luxurious 3BR villa in Maui's Ho'olei offers private elevator, gourmet kitchen, spacious lanais, beach access, pool with waterfall, jacuzzis, fitness center, and 24/7 security. Enjoy premium amenities in a gated community.
Location: Lahaina
Bedrooms: 4 - KFQTQF (sleeps 8)
5 (47 reviews)
Luxurious 4-bedroom, 4.5 bath home in Pineapple Hill, Kapalua Resort with ocean views, heated pool, gourmet kitchen, designer furniture, and golf discounts.
$1262/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKKK (sleeps 8)
4.8 (84 reviews)
Luxurious Hawaiian villa voted #1 resort in Hawaii by Conde Nast Reader’s Choice Awards 2019. Private balcony with partial ocean view, personal elevator, and beach access. Features a stunning pool, fitness center, and covered kitchen pavilion.
$632/nt (avg.)
Location: Kapalua Bay Villas , Kapalua
Bedrooms: 1 - K (sleeps 2)
5 (46 reviews)
Lovely 1BR/1.5BA condo in building #20 with private beach access, ocean views, fully equipped kitchen, central AC, and Cal-King Tempur-Pedic bed.
$1557/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKTTX (sleeps 10)
4.9 (61 reviews)
Luxurious 3BR/3.5BA villa with resort oasis pool, fitness area, and beach gear. Fully equipped kitchen, gaming systems, and flat screen TVs. Great location in Wailea near restaurants, shopping, and golf courses.
$3454/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKKX (sleeps 10)
5 (45 reviews)
Luxurious 3BR/3BA villa with ocean views from every bedroom, living room, and lanai. Sleeps up to 10. Resort amenities include 7 heated pools and beach access. Special pricing available. Free boogie boards and essential packages included.
$1517/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKKX (sleeps 8)
4.9 (59 reviews)
3-bedroom oceanfront residence with a wraparound balcony, Viking BBQ grill, luxury baths, and a well-appointed kitchen. The resort has 4 swimming pools, 5 hot tubs, Duke's Beach House Restaurant, Aina Gourmet Market, and Ho'ola Health Spa.
$2387/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKQQX (sleeps 10)
4.8 (77 reviews)
Experience luxury at Ho'olei 12-2 in Wailea, Maui. This 3BR, 3.5BA townhome offers a gourmet kitchen, private lanai, and access to a waterfall pool, saunas, and fitness center. Sleeps 10. Perfect for a relaxing tropical retreat.
$1518/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKDD (sleeps 8)
4.9 (57 reviews)
Escape to this Maui villa in a gated community with a pool, waterfall, and grotto. Enjoy a gourmet kitchen, spacious lanai, and private beach access. Stay 10+ nights for a free clean or 14+ nights for a free night.
$1804/nt (avg.)
Location: Kaanapali Alii , Kaanapali
Bedrooms: 2 - KK (sleeps 6)
5 (41 reviews)
Gorgeously remodeled and elegantly appointed, the oceanfront penthouse vantage point of residence 3-1106 boasts breathtaking Pacific Ocean views that stretch from Maui's neighbor islands of Lanai to Molokai and beyond.
Location: Hoolei , Wailea
Bedrooms: 3 - KQQ (sleeps 10)
5 (39 reviews)
Elegant, modern 3-bed vacation home in Wailea with stunning ocean views, outdoor patio with BBQ, high-top seating, and composite flooring. Access to 5-star pool, sauna, and waterfall. Walking distance to popular resort beaches and shops.
$2330/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKK (sleeps 8)
5 (36 reviews)
3BR oceanfront residence with a wraparound lanai, Viking BBQ, luxury baths, chef's kitchen, and Tommy Bahama beach chairs.
$4173/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKTT (sleeps 8)
4.9 (48 reviews)
Luxurious 3 bed, 3 bath villa on the 5th floor with stunning ocean views. Private outdoor kitchen, 7 heated pools, and top-of-the-line fitness center.
$1825/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKK (sleeps 8)
4.9 (48 reviews)
three-bedroom deluxe oceanview suite at Honua Kai with stunning views, a fully equipped kitchen, and free amenities such as beach chairs and BBQ equipment. The suite accommodates up to eight people
$756/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 2 - KTTX (sleeps 6)
4.9 (46 reviews)
Wailea Beach Villas is a luxurious penthouse with 2 bedrooms, a den, 2 full baths, and a spacious private covered lanai with built-in Viking grill.
$1751/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - QQXDX (sleeps 8)
5 (34 reviews)
Newly remodeled 2023! Spacious 3BR condo with bonus room in Ho'olei, stunning ocean/island views, sleeps 10. Enjoy beach gear, local snacks, and proximity to Wailea's shops, restaurants, and award-winning beaches. No resort fees!
$1431/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKDD (sleeps 6)
5 (34 reviews)
Luxurious Ho'olei Villa with stunning ocean views, spacious lanai, gourmet kitchen, and elegant decor. Enjoy a beautiful pool, fitness center, beach access, and central A/C. Special offers for extended stays. Ideal for relaxation in Maui!
$1694/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 2 - KK (sleeps 6)
4.9 (44 reviews)
Luxury 2-bed, 2-bath ocean view suite on the 6th floor with stunning views of Molokai. Honua Kai Resort boasts 7 heated pools, a beachfront restaurant, and a fitness center. Free boogie boards and packages including L'Occitane bath products, beach towels, and more.
$4164/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKKQQ (sleeps 8)
5 (32 reviews)
Luxurious 3BR/3.5BA oceanfront villa in Wailea. Steps from infinity pool & beach. Smart home features, private plunge pool, outdoor shower, & more.
$1144/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 2 - KDD (sleeps 6)
5 (32 reviews)
Escape to paradise at Polo Beach Club! Enjoy stunning ocean views, a newly remodeled pool and jacuzzi, and private access to Polo Beach. Our 2BR/2BA condo sleeps up to 6 guests and is fully equipped with all the amenities you need for a relaxing stay.
$3253/nt (avg.)
Location: Kihei
Bedrooms: 3 - KQTT (sleeps 6)
4.9 (43 reviews)
Luxurious 3BR/3BA beachfront home in Kihei. Privacy, ocean views, and walking distance to shops/restaurants. Lap pool, wading pool, and Jacuzzi.
Location: Hoolei , Wailea
Bedrooms: 3 - KKDD (sleeps 10)
4.9 (40 reviews)
Luxurious 3BR villa in a gated community with garden views, al fresco dining, a gourmet kitchen, and private lanais. Enjoy a stunning pool, jacuzzis, fitness center, and nearby beach access. Book 10+ nights for perks!
$966/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 1 - K (sleeps 2)
4.9 (35 reviews)
Luxury top floor condo with breathtaking ocean views, modern features, and fully equipped kitchen. Access to pool, jacuzzi, BBQ grills, and herb garden. Close to world-class dining and shopping options.
$6518/nt (avg.)
Location: Kihei
Bedrooms: 4 - KQKTQ (sleeps 8)
5 (26 reviews)
Moana Hideaway is a beachfront family-style home with ocean views, Italian leather sofas, central A/C, a beach-entry pool, hot tub, and cocktail cabana. The property includes a main house with 3 bedrooms and a separate cottage with 1 bedroom.
$1539/nt (avg.)
Location: Hoolei , Kihei
Bedrooms: 3 - KQTT (sleeps 10)
4.9 (35 reviews)
Luxurious 3,400 sq ft villa in Wailea's Ho'olei. Enjoy ocean views, private lanais, and gourmet kitchen. Walk to top beaches, shops, and dining. Access to five-star pool, saunas, and fitness center. Ideal for relaxation and adventure.
$1189/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KQQQ (sleeps 8)
4.8 (47 reviews)
Luxury 3BR villa in a gated community with 24-hour security, private elevator, stunning pool, beach access, modern furnishings, and top of the line appliances.
$1093/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 2 - KK (sleeps 6)
4.9 (33 reviews)
premier 2-bedroom suite at Honua Kai Resort and Spa. The suite has ocean views, a large balcony, fully equipped kitchen, and luxurious amenities. The resort has pools, beach access, and an on-site restaurant.
$2867/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - (sleeps 8)
4.9 (32 reviews)
Experience a luxurious 3-bed, 3-bath villa on the 4th floor of Honua Kai Resort in Maui, with ocean views, high-end furnishings, and gourmet kitchen. Enjoy the resort's 5-star amenities, including 7 heated pools, 16 Viking BBQs, and Duke's Beach House Restaurant.
$2093/nt (avg.)
Location: Kapalua Bay Villas , Kapalua
Bedrooms: 1 - (sleeps 2)
5 (23 reviews)
Oceanfront Hawaiian villa w/ stunning views & private walkway. Free 4-door car for 6+ night stays. Access to heated pools, BBQ, golf, tennis & local dining. Luxury amenities & vacation packages included.
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKKT (sleeps 8)
5 (23 reviews)
Azure Azul M212 is a 3-bedroom, 3-bath ocean view corner unit at Wailea Beach Villas, Maui Island. It has a covered wrap-around veranda, new electronics and furnishings, a full kitchen, and access to resort amenities like pools and fitness center.
$2873/nt (avg.)
Location: The Resort at Kapalua Bay , Kapalua
Bedrooms: 4 - XKFKK (sleeps 8)
4.9 (30 reviews)
Ocean Dreams Villa 2203 is a luxurious 3-bedroom vacation rental with stunning ocean views, a well-equipped kitchen, and access to Montage Resort amenities.
Location: Wailea Beach Villas , Wailea
Bedrooms: 2 - KTTX (sleeps 6)
5 (22 reviews)
Luxury penthouse at Wailea Beach Villas. Pacific Ocean views, full kitchen, open floor plan, private lanai w/ gas grill, den, main bedroom w/ en-suite bath, 2nd bedroom (twin/king). Amenities: TVs, gym, 2 pools w/ spas, beach set-up, close to Wailea Shops.
Location: Kihei
Bedrooms: 3 - KQKT (sleeps 6)
5 (21 reviews)
Mango Surf is a 3-bedroom beachfront home with a heated swimming pool, hot tub, and ocean views. It has central air conditioning, a renovated kitchen, and new furnishings. The property features a large grass lawn, a mature mango tree, and a quiet setting.
$2252/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 2 - (sleeps 6)
4.9 (28 reviews)
Luxury 2 bed, 3 bath oceanfront corner suite. 5-star amenities at Honua Kai Resort incl. 7 heated pools, fitness center, and beachfront location.
$2270/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 4 - QKTKKT (sleeps 8)
4.7 (49 reviews)
Luxurious 3300 sq condo with 4 bedrooms, 2 master suites, Waterworks Bathrooms, Viking barbecue, infinity pool, gym, and private entrance to shops.
$4519/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - (sleeps 8)
5 (20 reviews)
Luxury Villa, Large 2230 sqft Interior + Lanai, 3 Bed, 3 Bath, Sleeps 8
Location: The Resort at Kapalua Bay , Kapalua
Bedrooms: 3 - (sleeps 10)
5 (18 reviews)
Luxe 3BR/3.5BA Kapalua Bay villa with sweeping ocean views, 2,900 sq ft plus 1,200 sq ft lanai with grill. Viking chef's kitchen. Housekeeping/turndown included. Resort pools, beachfront, spa. Free car on 6+ nights.
$1875/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKQ (sleeps 8)
4.9 (24 reviews)
Bali Hai is a 3-bed, 3.5-bath garden level pool villa with over 3,500 sq ft of indoor/outdoor living space. It has a private plunge pool, outdoor grotto shower, and a large wrap-around lawn. The villa has a full kitchen, multiple work desks, and complimentary Netflix.
$1422/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKK (sleeps 6)
4.9 (23 reviews)
Luxurious 3 bed, 3.5 bath villa in Maui voted #1 Resort in Hawaii by Conde Nast Reader’s Choice Awards 2019. Private, designer furnishings, pool, hot tub, fitness area, beach access, and parking for 2 vehicles. Fully equipped kitchen, AC, elevator, beach chairs, and towels.
$1689/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKKT (sleeps 6)
5 (17 reviews)
Sea Breeze Suite J405 is a luxurious 3-bed, 3-bath vacation rental with stunning ocean views, state-of-the-art technology, and high-end furnishings.
$956/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 2 - KKX (sleeps 6)
5 (17 reviews)
Premier Honua Kai 2BR suite with stunning ocean views from every room & spacious wraparound lanai. Includes an "Ohana Play Package" for beach fun, professional kitchen, and local Moku Pua bath amenities. Voted among top 10 Hawaiian resorts by Conde Nast.
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKF (sleeps 8)
5 (16 reviews)
Private 3 bed, 3.5 bath villa with garden, plunge pool, outdoor shower, and full kitchen at Wailea Beach Villas resort. Direct access to Wailea Beach.
$3902/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - QQ (sleeps 8)
4.9 (21 reviews)
Luxurious 3BR/3BA oceanfront unit with stunning Pacific Ocean views, gourmet kitchen, private BBQ, and sleeps up to 10 guests. Honua Kai Resort amenities include 7 heated pools, Duke's Beach House Restaurant, fitness center, and Ho'ola Health Spa.
$2851/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 3 - KKQQX (sleeps 9)
4.9 (21 reviews)
Newly launched Honua Kai 3BR oceanfront residence with stunning views, luxurious amenities, gourmet kitchen, and access to aquatic playground and spa.
$1295/nt (avg.)
Location: Kaanapali Alii , Kaanapali
Bedrooms: 2 - KQQ (sleeps 6)
4.9 (19 reviews)
"Premier Kaanapali rental with ocean views, luxury finishes, & top-tier amenities. Free shuttle, beach package, local bath amenities included. Near beach, offers poolside BBQ, fitness, spa, tennis. Prime whale watching in winter. Ideal for family vacations."
Location: The Resort at Kapalua Bay , Kapalua
Bedrooms: 3 - KQK (sleeps 8)
5 (14 reviews)
Expansive 3rd floor villa with beautiful artwork, vaulted ceilings, custom woodwork, and large granite island. Includes free night discounts and luxury amenities.
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKKT (sleeps 6)
5 (14 reviews)
Aqua Lani J305 is a luxurious 3-bedroom villa with panoramic ocean views, upscale interior appointments, and original art pieces. It features plush ultra-premium beds, a chef's culinary dream kitchen, and a large outdoor terrace.
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Maui luxury rentals FAQ

What makes a rental luxury on HawaiiGaga?

We choose rather than filter by price. Three resorts - The Resort at Kapalua Bay, Wailea Beach Villas and Ho'olei - are on a level of their own, so all their residences are in. At the next tier (Honua Kai, Kaanapali Alii, Kapalua Bay Villas, Polo Beach Club and Makena Surf) a unit must be rated 4.9 or higher by at least 10 guests, have a verified ocean view and be priced like the building's best. Estate homes need air conditioning, a pool or the ocean out front, and a 4.8+ rating from at least 10 guests. Owners can't pay to be included.

Should I book a villa or a five-star hotel?

For a family or a group, usually a villa: two to four bedrooms with their own baths, a full kitchen, laundry and a big lanai often cost less than the equivalent hotel rooms and keep everyone together. A hotel wins on daily housekeeping, room service, kids' clubs and having everything on site. For some of both, The Resort at Kapalua Bay pairs private residences with a full resort, and Wailea Beach Villas has beach attendants and a concierge.

Which Maui luxury rentals are on the beach?

Wailea Beach Villas (Wailea Beach), Polo Beach Club (Polo Beach), Makena Surf (Paipu Beach), Kaanapali Alii (Kaanapali Beach) and Honua Kai (North Kaanapali Beach) are on the sand. In Kapalua, The Resort at Kapalua Bay is a short walk above Kapalua Bay and the Bay Villas overlook Oneloa Bay, and several estate homes are oceanfront. Select Beachfront or Oceanfront in Search Filters to narrow the list.

Wailea, Kapalua or Kaanapali?

Wailea for sunshine, fine dining and the beach walk that links its resorts, with quieter Makena just south. Kapalua for a greener, more secluded resort with coastal trails, golf and some of Maui's best bays. Kaanapali for a lively beach scene, with Whalers Village, Black Rock and restaurants along the beach walk.

When should I book?

As early as you can. We list only a few dozen top-tier residences, and holiday weeks at these resorts book up to a year ahead, often with longer minimum stays.

Do these rentals come with resort services?

It depends on the building. Wailea Beach Villas has beach attendants and a concierge, Kaanapali Alii a 24-hour front desk and a seasonal kids' club, and Honua Kai a restaurant, market and spa on site. Most residences are rented by their owners or local agencies, so housekeeping, fees and extras vary from one rental to the next - check each listing.

Keep researching: Wailea condos · Kapalua condos · Maui beachfront rentals · Maui oceanfront rentals · Maui condo guide · Maui vacation rentals