Title: 5 Stars Hotels in Olowalu, Hawaii from CA $374 - Find Cheap Olowalu Hotels With 5 Stars | Expedia.ca [Olowalu Travel Guide](https://expedia.ca/Olowalu.dx11584)[Hotels in Olowalu](https://expedia.ca/Olowalu-Hotels.d11584.Travel-Guide-Hotels)[Vacation Rentals in Olowalu](https://expedia.ca/Olowalu-Vacation-Rentals.d11584.Travel-Guide-VacationRentals)[Flights to Olowalu](https://expedia.ca/Cheap-Flights-To-Olowalu.d11584.Travel-Guide-Flights)[Things to do in Olowalu](https://expedia.ca/Things-To-Do-In-Olowalu.d11584.Travel-Guide-Activities)[Olowalu Car Rentals](https://expedia.ca/Car-Rentals-In-Olowalu.d11584.Car-Rental-Guide)[Olowalu Vacation Packages](https://expedia.ca/Olowalu.d11584.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/1fd0a2141e0e85258825cdd377019eb4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Claire Houston # 5 Stars Hotels in Olowalu, Hawaii from CA $374 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Olowalu 5 Star Hotels Tonight [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=11584&startDate=2025-10-27&endDate=2025-10-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=11584&startDate=2025-10-28&endDate=2025-10-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=11584&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=11584&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Olowalu 5 Star Hotels ![Club Ocean Front One Bedroom Suite](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/f9c45622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/0069cac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Maile Three-Bedroom Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/2cdd56af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Resort Maui at Wailea Wailea 9.6/10 Exceptional (1003) "Prime location to enjoy the Hawaiian natural beauty from the pools or while dining. Helpful and professional staff, from front desk to housekeeping. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mohammad CA $1,043 CA $1,230 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ![3 outdoor pools, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/w3996h2667x0y0-f44bed53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/99ce1291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand, free beach shuttle, beach cabanas](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/3545b597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/33deff2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton Maui, Kapalua Kapalua 9.0/10 Wonderful (1003) "Really nice property with excellent amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tatiana CA $1,188 CA $1,493 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![9 outdoor pools, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/8788f08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3837h2557x3y3-5ebfbeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/813399da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Wailea Maui, A Waldorf Astoria Resort Wailea 8.8/10 Excellent (1013) "Wonderful accommodations!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $808 CA $1,043 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/e8ef7f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, 1 Bedroom, Kilohana Corner Suite, (1 King Bed) | Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/04bfdd03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/b17d91a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Kea Lani Maui Wailea 9.4/10 Exceptional (1018) "Amazing hotel I would stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ERIKA CA $1,105 CA $1,386 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![Breakfast, lunch, dinner served; alfresco dining](https://images.trvl-media.com/lodging/1000000/30000/24600/24502/5c3953dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/30000/24600/24502/262a9930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/30000/24600/24502/4a772e31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/24600/24502/3548c7b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sensei Lanai, A Four Seasons Resort Lanai City 9.8/10 Exceptional (135) "great stay, great experience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ardalan [](https://www.expedia.ca/Lanai-City-Hotels-Sensei-Lanai.h24502.Hotel-Information) ![Lanai](https://images.trvl-media.com/lodging/1000000/10000/3000/2980/f1a2e820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/3000/2980/99682edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3000/2980/3ef09912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Manele) | Living area](https://images.trvl-media.com/lodging/1000000/10000/3000/2980/330a885d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Resort Lanai Lanai City 9.8/10 Exceptional (219) "Absolutely a wonderful experience, fabulous staff and amenities!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) lynn CA $1,470 CA $1,734 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Lanai-City-Hotels-Four-Seasons-Resort-Lanai.h2980.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/51e44f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Regional cuisine](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/65eee840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/d4acdf82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Regional cuisine](https://images.trvl-media.com/lodging/1000000/90000/85500/85412/ee7d62b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Wailea, Relais & Chateaux - Adults Only Wailea 9.4/10 Exceptional (1002) "Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $1,258 CA $1,567 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information) ![On the beach, beach towels, snorkeling, surfing](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/a0787557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/55a663a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/523d64b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch served, American cuisine, pool views ](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/58212487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay Lahaina 9.6/10 Exceptional (204) "We used Spa, expedia mentioned there is 20% discount and we didn't get it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ronak CA $1,400 CA $1,800 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Lahaina-Hotels-Montage-Kapalua-Bay.h5914192.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/0e84672f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/4f26861d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/3bd64cf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Kayaking](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/21935658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ho‘olei Villas at Grand Wailea Wailea 9.6/10 Exceptional (44) "Perfect for Families. Quite spacious and great for a relaxing Family vacation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $2,782 CA $3,372 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Kihei-Hotels-Hoolei-At-Grand-Wailea.h1661500.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/w5464h3630x0y5-53069acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/231f7809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/4021aaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/732f839b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Royal Lahaina Bungalows & Spa Lahaina CA $390 CA $535 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Lahaina-Hotels-Royal-Lahaina-Bungalows-Spa.h115794140.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/c0b8dfb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/8232475d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/29664a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, swim-up bar, poolside bar](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/eb7843a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Kea Lani Maui Villa Experience Wailea 9.8/10 Exceptional (6) "It’s a decent hotel to stay for the family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sze Wai CA $3,917 CA $4,703 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui-Villa-Experience.h37220226.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/f537c1fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Living area](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/a0ab1941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Living area](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/c6acb995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100970000/100963600/100963582/98e97d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 2 Oceanview Modern Resort Vistas Central Kihei 10/10 Exceptional (5) "This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jarrod [](https://www.expedia.ca/Kihei-Hotels-2-2-Oceanview-Modern-Resort-Vistas.h100963582.Hotel-Information) ![Luxury Apartment | Private kitchen](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/46d854e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment | Private kitchen](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/45c2cce5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment | Beach/ocean view](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/725c39a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment | Private kitchen](https://images.trvl-media.com/lodging/100000000/99780000/99778400/99778371/53237f33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wailea Luxury Hilltop Resort Vistas Wailea 10/10 Exceptional (2) "very nice place and location 🤗" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maryna [](https://www.expedia.ca/Kihei-Hotels-Wailea-Luxury-Hilltop-Resort-Vista.h99778371.Hotel-Information) ![Luxury Condo | Balcony](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/26b6bec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Private kitchen](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/4d0d378f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Extra beds](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/7861cddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo | Balcony](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/62eb8040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centrally Located Elegant Vistas South Kihei 10/10 Exceptional (1) "Love this Kihei home! Centrally located! It is very clean. We love that they have beach chairs and towels on hand. Overall great experience stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edwin [](https://www.expedia.ca/Kihei-Hotels-Centrally-Located-Elegant-Vistas.h96448155.Hotel-Information) ![Outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/aaadbf4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/605dcf2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, Ocean View | Living area](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/c44f01d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/dac19e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Kihei Paradise Vistas Central Kihei 10/10 Exceptional (2) "This property was clean, quiet, and had excellent security. The barbecue grill was easy to use. They had sandless beach towels, which worked so well. The view was beautiful! I want to go again next year. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mae [](https://www.expedia.ca/Kihei-Hotels-Oceanfront-Kihei-Paradise-Vistas.h103891972.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/82bc9789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/b551e971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, 2 Bedrooms, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/60aecbec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, 2 Bedrooms, Kitchen, Ocean View | Living area](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/6e2825db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale Luxurious Ocean Resort Vistas South Kihei [](https://www.expedia.ca/Kihei-Hotels-Upscale-Luxurious-Ocean-Resort-Vistas.h102687821.Hotel-Information) ![Condo (5 Bedrooms) | Pool](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434367/b24bbd29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (5 Bedrooms) | View from room](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434367/3ffb9acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (5 Bedrooms) | Dining](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434367/e39db4dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (5 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434367/cf5d4a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Honua Kai Konea Collection by KBM - 3 Units on same floor (812/816/820) Kaanapali [](https://www.expedia.ca/Kaanapali-Hotels-Spacious-5-Bedroom-Honua-Kai-Collection-Multi-Unit-Listing-Same-Floor-Ocean-Glimpses-3-Free-Rental-Cars-Hkk-8121620.h117434367.Hotel-Information) ![Condo (6 Bedrooms) | Property entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/a977472e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | View from room](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/e5bedc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Property entrance](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/ed5ea160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Beach](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/a0b26604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206) Kapalua [](https://www.expedia.ca/Kapalua-Hotels-Spacious-6-Bedroom-Montage-Kapalua-Collection-Multi-Unit-Listing-Same-Floor-Ocean-Views-2-Free-Rental-Cars-Mon-22042206.h116973003.Hotel-Information) ![Condo (6 Bedrooms) | Pool](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/c9696859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Terrace/patio](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/w1918h1280x0y0-cb6a6863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Dining](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/c3352339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms)](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973002/f21063a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401) Kapalua [](https://www.expedia.ca/Kapalua-Hotels-Spacious-6-Bedroom-Montage-Kapalua-Collection-Multi-Unit-Listing-Different-Floors-Ocean-Views-2-Free-Rental-Cars-Mon-63016401.h116973002.Hotel-Information) ![Condo (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/d5403ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Living room](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/9dda6fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/5b46714a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Dining](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/c232b144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### KBM Resorts Free CAR Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Mon-5203 Kapalua [](https://www.expedia.ca/Kapalua-Hotels-KBM-Resorts-Luxury-Oceanfront-Villa-At-Montage-Kapalua-Bay-Private-Lanai-And-BBQ-Free-Rental-Car-Malia-At-Montage-Kapalua-Bay.h119312427.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Olowalu-Hotels.s50-0-d11584.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Olowalu-Hotels.s50-0-d11584.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Olowalu. ![Royal Lahaina Resort & Bungalows](https://images.trvl-media.com/lodging/1000000/40000/34800/34767/8a8031c5_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Royal Lahaina Resort & Bungalows 2780 Kekaa Dr, Lahaina, HI CA $254 CA $374 total Nov 20 - Nov 21 includes taxes & fees 8.4/10 Very Good! (1,503 reviews) [](https://expedia.ca/Kaanapali-Hotels-Royal-Lahaina-Resort-Bungalows.h34767.Hotel-Information) ![The Westin Maui Resort & Spa, Ka'anapali](https://images.trvl-media.com/lodging/1000000/30000/25900/25837/87f76342_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Westin Maui Resort & Spa, Ka'anapali 2365 Kaanapali Pkwy, Lahaina, HI CA $609 CA $799 total Oct 28 - Oct 29 includes taxes & fees 9/10 Wonderful! (1,006 reviews) [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ![Andaz Maui at Wailea Resort - a concept by Hyatt](https://images.trvl-media.com/lodging/1000000/10000/2600/2552/487d8e2d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Andaz Maui at Wailea Resort - a concept by Hyatt 3550 Wailea Alanui Dr, Kihei, HI CA $1,069 CA $1,344 total Nov 25 - Nov 26 includes taxes & fees 9.2/10 Wonderful! (997 reviews) [](https://expedia.ca/Kihei-Hotels-Andaz-Maui-At-Wailea-Resort-A-Concept-By-Hyatt.h2552.Hotel-Information) Still don't see what you're looking for? [See all properties in Olowalu.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F10%2F2025&endDate=29%2F10%2F2025®ionId=11584&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F10%2F2025&endDate=29%2F10%2F2025®ionId=11584&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F10%2F2025&endDate=29%2F10%2F2025®ionId=11584&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F10%2F2025&endDate=29%2F10%2F2025®ionId=11584&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F10%2F2025&endDate=29%2F10%2F2025®ionId=11584&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F10%2F2025&endDate=29%2F10%2F2025®ionId=11584&star=50&star=50&amenities=WATER_PARK) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## Learn more about Olowalu Trip time! Discover the local cuisine and beaches in romantic Olowalu. [See all hotels in Olowalu](https://www.expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&adults=2®ionId=11584) ![Super epic coral and some really good sea life! Right off the beach. All you need is the gear. You don't need any tours or anything at all :) ](https://images.trvl-media.com/place/6069111/2b2be4fe-a153-483b-8b00-3de5bd3ee06a.jpg?impolicy=fcrop&w=416&h=416&p=1&q=high) Photo by Chris Fiegel ## Top Olowalu Hotel Reviews ![Fairmont Kea Lani Maui](//images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "Lovely property, rooms were spacious. House keeping came daily. Plenty of pool chairs. Beach access was great. Restaurant choices were fabulous especially the new sushi restaurant upstairs. One restaurant was being remodeled but you never heard any construction " [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![Grand Wailea Maui, A Waldorf Astoria Resort](//images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg) ### Grand Wailea Maui, A Waldorf Astoria Resort 10/10 Excellent "Everything was wonderful " [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![The Ritz-Carlton Maui, Kapalua](//images.trvl-media.com/lodging/1000000/10000/3400/3390/w3996h2667x0y0-f44bed53_y.jpg) ### The Ritz-Carlton Maui, Kapalua 10/10 Excellent "Amazing." [](https://expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![Four Seasons Resort Maui at Wailea](//images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193_y.jpg) ### Four Seasons Resort Maui at Wailea 10/10 Excellent "Prime location to enjoy the Hawaiian natural beauty from the pools or while dining. Helpful and professional staff, from front desk to housekeeping. " [](https://expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ## Find out more about Olowalu ## Five Star Hotels in Olowalu There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Olowalu so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Olowalu and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Olowalu Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Olowalu The results are in, and Olowalu 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Olowalu! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Olowalu today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Olowalu? > There are a range of pricing options for 5-star hotels in Olowalu on Expedia. How much you'll pay will depend on when you plan to travel, length of stay and other factors. Compare all of the available properties for your chosen dates and use our pricing and other filters to find the perfect upscale stay. > > > > - Search for the lowest price per night from CA $374 ### What makes a hotel 5 stars in Olowalu? > In Olowalu, a hotel must provide a specific level of high-end conveniences to be designated 5 stars. These may include gourmet restaurants, saunas and spas, on-site gyms, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their superior service. You'll enjoy things like concierge services, in-room massages and nightly turn-down services. Some may also offer special touches such as a welcome gift. ### Are there any 5-star all-inclusive resorts in Olowalu? > Expedia's filter tool is the easiest way to find exactly what you want. Check the "All inclusive" and "5-star" boxes to show the most luxurious resorts in Olowalu where your accommodations, meals, entertainment and activities are included in the price. 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[Cheap Hotels in Lahaina](https://www.expedia.ca/Lahaina-Hotels-Cheap-Hotels.0-0-d8499-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Lahaina](https://www.expedia.ca/Lahaina-Hotels-Hilton-Hotels.0-0-d8499--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Lahaina](https://www.expedia.ca/Lahaina-Hotels-Historic-Hotel.0-0-d8499-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Lahaina](https://www.expedia.ca/Lahaina-Hotels-Honeymoon-Hotels.0-0-d8499-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Lahaina](https://www.expedia.ca/Lahaina-Hotels-LGBT-Friendly-Hotel.0-0-d8499-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Lahaina](https://www.expedia.ca/Lahaina-Hotels-Oceanfront-Hotels.0-0-d8499-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Outrigger Hotels in Lahaina](https://www.expedia.ca/Lahaina-Hotels-Outrigger.0-0-d8499--bOutrigger.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Lahaina](https://www.expedia.ca/Lahaina-Hotels-Shopping-Hotel.0-0-d8499-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Lahaina Hotels](https://www.expedia.ca/Lahaina-Hotels.d8499.Travel-Guide-Hotels) - [Vacation Homes in Lahaina](https://www.expedia.ca/Lahaina-Private-Vacation-Homes.d8499-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Resorts in Lahaina](https://www.expedia.ca/Lahaina-Resort-Hotels.d8499-aaResortHotels.Travel-Guide-Accommodation) - [Villas in Lahaina](https://www.expedia.ca/Lahaina-Villas.d8499-aaVillas.Travel-Guide-Accommodation) - [Hotels near Launiupoko Beach Park](https://www.expedia.ca/Launiupoko-Beach-Park-Hotels.0-l553248621532639172-0.Travel-Guide-Filter-Hotels) - [Vacation Homes in Launiupoko](https://www.expedia.ca/Launiupoko-Private-Vacation-Homes.d553248635976417062-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Maui Hotels](https://www.expedia.ca/Maui-Hotels.d180073.Travel-Guide-Hotels) - [Hotels near Puamana Beach Park](https://www.expedia.ca/Puamana-Beach-Park-Hotels.0-l553248635976194355-0.Travel-Guide-Filter-Hotels) - [Flights to Lahaina](https://www.expedia.ca/Cheap-Flights-To-Lahaina.d8499.Travel-Guide-Flights) - 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[Flights from Kahului to Lahaina](https://www.expedia.ca/lp/flights/2646/8499/kahului-to-lahaina) - [Flights from Saskatoon to Lahaina](https://www.expedia.ca/lp/flights/4117/8499/saskatoon-to-lahaina) - [Flights from Rock Springs to Lahaina](https://www.expedia.ca/lp/flights/6055874/8499/rock-springs-to-lahaina) - [Flights from Winnipeg to Lahaina](https://www.expedia.ca/lp/flights/6141041/8499/winnipeg-to-lahaina) - [Flights from Lahaina](https://www.expedia.ca/lp/flights/8499/flights-from-lahaina) - [Visit Downtown Lahaina](https://www.expedia.ca/Lahaina-Downtown-Lahaina.dx6140626) - [Lahaina Vacations](https://www.expedia.ca/Lahaina.d8499.Destination-Travel-Guides) - [Visit Lahaina](https://www.expedia.ca/Lahaina.dx8499) - [Launiupoko Beach Park](https://www.expedia.ca/Launiupoko-Beach-Park-Hawaii.d553248621532639172.Vacation-Attraction) - [Avis Rental Cars in Lahaina](https://www.expedia.ca/Avis-Car-Rentals-In-Lahaina.d8499-c41.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Lahaina](https://www.expedia.ca/Budget-Car-Rentals-In-Lahaina.d8499-c39.Car-Rental-Guide-Suppliers) - [Car rentals near Downtown Lahaina](https://www.expedia.ca/Car-Rentals-In-Downtown-Lahaina.d6140626.Car-Rental-Guide) - [Car rental Lahaina](https://www.expedia.ca/Car-Rentals-In-Lahaina.d8499.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in Lahaina](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Lahaina.d8499-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Lahaina](https://www.expedia.ca/Enterprise-Car-Rentals-In-Lahaina.d8499-c15.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Lahaina](https://www.expedia.ca/Hertz-Car-Rentals-In-Lahaina.d8499-c40.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in Lahaina](https://www.expedia.ca/Payless-Car-Rentals-In-Lahaina.d8499-c38.Car-Rental-Guide-Suppliers) - [Things to do in Lahaina](https://www.expedia.ca/Things-To-Do-In-Lahaina.d8499.Travel-Guide-Activities) - [Book 5 Star Hotels in Olowalu on Expedia.com](https://www.expedia.com/5Star-Olowalu-Hotels.s50-0-d11584.Travel-Guide-Filter-Hotels)