Hand-picked Hawaii vacation rentals & condos Every view checked

Maui Luxury Rentals: Up to 2 Bedrooms


HawaiiGaga LuxuryShowing only the rentals that make our luxury list · How we choose · Show all rentals
« New Search
Search results (30)
$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.
$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.
$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.
$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.
$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.
$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.
$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."
$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.
$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.
$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.
$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..
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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: 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.
$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.
$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.
$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."
$2384/nt (avg.)
Location: Honua Kai Resort , Kaanapali
Bedrooms: 2 - KKTTX (sleeps 6)
5 (12 reviews)
Luxury 2-BR Hawaiian villa with ocean views, large balcony, and top amenities. Complimentary car rental for bookings 6+ nights. Includes king beds, private baths, equipped kitchen, access to beachfront resort with heated pools, dining, BBQ, gym, spa. Sleeps six.