Title: 5 Stars Hotels in Olowalu, Hawaii from CA $649 - 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) ![Coconut tree sunset. #beachbound](https://images.trvl-media.com/place/11584/24198524-4e21-4952-977e-7a7bf0986e37.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ryan Fuller # 5 Stars Hotels in Olowalu, Hawaii from CA $649 - ![](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 [Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=11584&startDate=2025-12-31&endDate=2026-01-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 1 - Jan 2](https://www.expedia.ca/Hotel-Search?regionId=11584&startDate=2026-01-01&endDate=2026-01-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=11584&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=11584&startDate=2026-01-09&endDate=2026-01-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/a0a6da1a.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) ![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) ### Four Seasons Resort Maui at Wailea [](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) Wailea 9.6/10 Exceptional (1000) "Beautiful property, efficient staff, truly a wonderful stay " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Angela CA $1,088 CA $1,292 total includes taxes & fees Jan 26 - Jan 27, 2026 [](https://www.expedia.ca/Kihei-Hotels-Four-Seasons-Resort-Maui-At-Wailea.h14336.Hotel-Information) ![7 restaurants, breakfast served](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/813399da.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) ### Grand Wailea Maui, A Waldorf Astoria Resort [](https://www.expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) Wailea 8.8/10 Excellent (1006) "Very nice resort for a family vacation!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashwini CA $938 CA $1,202 total includes taxes & fees Jan 14 - Jan 15, 2026 [](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) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/b17d91a7.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/2d5cd1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Kea Lani Maui [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) Wailea 9.4/10 Exceptional (1002) "Wonderful staff and facility" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheila CA $1,290 CA $1,613 total includes taxes & fees Jan 31 - Feb 1, 2026 [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.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) ![On the beach, 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) ![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) ![On the beach, white sand, free beach shuttle, beach cabanas](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/863b2be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton Maui, Kapalua [](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) Kapalua 9.2/10 Wonderful (1001) "Top notch property with amazing service and staff" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Delaine CA $1,094 CA $1,388 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.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/1000000/10000/3000/2980/7a6e3265.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) ![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) ### Four Seasons Resort Lanai [](https://www.expedia.ca/Lanai-City-Hotels-Four-Seasons-Resort-Lanai.h2980.Hotel-Information) Lanai City 9.8/10 Exceptional (222) "Absolutely a wonderful experience, fabulous staff and amenities!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) lynn CA $1,787 CA $2,122 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Lanai-City-Hotels-Four-Seasons-Resort-Lanai.h2980.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) ![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) ![Body treatments, hot stone massages, deep-tissue massages, body wraps](https://images.trvl-media.com/lodging/1000000/30000/24600/24502/03139b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sensei Lanai, A Four Seasons Resort [](https://www.expedia.ca/Lanai-City-Hotels-Sensei-Lanai.h24502.Hotel-Information) 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) ![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 [](https://www.expedia.ca/Kihei-Hotels-Hotel-Wailea.h85412.Hotel-Information) Wailea 9.4/10 Exceptional (1003) "Staff was great and the property was stunning. It was everything we wanted for our honeymoon. Other couples mentioned " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob CA $1,436 CA $1,786 total includes taxes & fees Jan 7 - Jan 8, 2026 [](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) ![View from room](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/c3ab62d2.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) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/6000000/5920000/5914200/5914192/55a663a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montage Kapalua Bay [](https://www.expedia.ca/Lahaina-Hotels-Montage-Kapalua-Bay.h5914192.Hotel-Information) 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 $1,834 CA $2,373 total includes taxes & fees Jan 25 - Jan 26, 2026 [](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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661500/w3837h2207x3y3-85d53f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ho‘olei Villas at Grand Wailea [](https://www.expedia.ca/Kihei-Hotels-Hoolei-At-Grand-Wailea.h1661500.Hotel-Information) 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 $2,774 CA $3,381 total includes taxes & fees Jan 8 - Jan 9, 2026 [](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) ![Garden](https://images.trvl-media.com/lodging/116000000/115800000/115794200/115794140/732f839b.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) ### Royal Lahaina Bungalows & Spa [](https://www.expedia.ca/Lahaina-Hotels-Royal-Lahaina-Bungalows-Spa.h115794140.Hotel-Information) Lahaina 9.0/10 Wonderful (2) "Clean room and staff is super friendly. Would stay here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rene CA $581 CA $762 total includes taxes & fees Jan 10 - Jan 11, 2026 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/38000000/37230000/37220300/37220226/03d12ddf.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) ### Fairmont Kea Lani Maui Villa Experience [](https://www.expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui-Villa-Experience.h37220226.Hotel-Information) 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 $3,957 CA $4,748 total includes taxes & fees Jan 8 - Jan 9, 2026 [](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/c6acb995.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) ![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 [](https://www.expedia.ca/Kihei-Hotels-2-2-Oceanview-Modern-Resort-Vistas.h100963582.Hotel-Information) Central Kihei 9.8/10 Exceptional (7) "The condo was very clean, loved all of the decor, was very beautiful. Had everything you could possibly need in kitchen and bathrooms. Would definitely stay again! Everyone we talked to was very nice and helpful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulina [](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 | 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/100000000/99780000/99778400/99778371/45c2cce5.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 [](https://www.expedia.ca/Kihei-Hotels-Wailea-Luxury-Hilltop-Resort-Vista.h99778371.Hotel-Information) 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) ![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) ![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](https://images.trvl-media.com/lodging/104000000/103900000/103892000/103891972/0b8f6070.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 [](https://www.expedia.ca/Kihei-Hotels-Oceanfront-Kihei-Paradise-Vistas.h103891972.Hotel-Information) 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) ![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 | Balcony](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/62eb8040.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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/97000000/96450000/96448200/96448155/d5c0e23e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centrally Located Elegant Vistas [](https://www.expedia.ca/Kihei-Hotels-Centrally-Located-Elegant-Vistas.h96448155.Hotel-Information) 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) ![Condo (3 Bedrooms) | Pool](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/c4870c78.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) ![Condo (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/b354f323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Beach](https://images.trvl-media.com/lodging/120000000/119320000/119312500/119312427/e4b0acbe.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 [](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) 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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102690000/102687900/102687821/d2dcf4e1.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) ### Upscale Luxurious Ocean Resort Vistas [](https://www.expedia.ca/Kihei-Hotels-Upscale-Luxurious-Ocean-Resort-Vistas.h102687821.Hotel-Information) 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/f0e1cbec.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) | Private kitchen](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434367/cf5d4a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (5 Bedrooms) | Restaurant](https://images.trvl-media.com/lodging/118000000/117440000/117434400/117434367/770ad24c.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) [](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) 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) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/362be129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (6 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/117000000/116980000/116973100/116973003/3b4ba262.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) [](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) 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 (3 Bedrooms) | Pool](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/8d834930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/d56dba91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | Beach](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/95de64d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (3 Bedrooms) | View from room](https://images.trvl-media.com/lodging/120000000/119720000/119719200/119719148/w1913h1269x0y9-fb752a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW KBM Resorts Free CAR Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-bedroom Condo With Daily Housekeeping, Spa! Mon-6302 [](https://www.expedia.ca/NEW-KBM-Resorts-Free-CAR-Hale-Nalu-At-Montage-Kapalua-Bay.h119719148.Hotel-Information) Kapalua [](https://www.expedia.ca/NEW-KBM-Resorts-Free-CAR-Hale-Nalu-At-Montage-Kapalua-Bay.h119719148.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. ![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 $660 CA $863 total Jan 9 - Jan 10, 2026 includes taxes & fees 9/10 Wonderful! (1,009 reviews) [](https://expedia.ca/Kaanapali-Hotels-The-Westin-Maui-Resort-Spa.h25837.Hotel-Information) ![Sheraton Maui Resort & Spa](https://images.trvl-media.com/lodging/1000000/30000/22900/22894/w4000h2664x0y0-b7d636ba_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sheraton Maui Resort & Spa 2605 Kaanapali Pkwy Lahaina HI CA $687 CA $895 total Jan 20 - Jan 21, 2026 includes taxes & fees 8.6/10 Excellent! (1,003 reviews) [](https://expedia.ca/Kaanapali-Hotels-Sheraton-Maui-Resort-Spa.h22894.Hotel-Information) ![Hilton Vacation Club Ka'anapali Beach Maui](https://images.trvl-media.com/lodging/1000000/30000/23100/23042/7a9e8592_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Vacation Club Ka'anapali Beach Maui 104 Ka'anapali Shores Place Kaanapali HI CA $506 CA $649 total Jan 18 - Jan 19, 2026 includes taxes & fees 8.8/10 Excellent! (1,001 reviews) [](https://expedia.ca/Lahaina-Hotels-Kaanapali-Beach-Club.h23042.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=01%2F01%2F2026&endDate=02%2F01%2F2026®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=01%2F01%2F2026&endDate=02%2F01%2F2026®ionId=11584&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F01%2F2026&endDate=02%2F01%2F2026®ionId=11584&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F01%2F2026&endDate=02%2F01%2F2026®ionId=11584&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F01%2F2026&endDate=02%2F01%2F2026®ionId=11584&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=01%2F01%2F2026&endDate=02%2F01%2F2026®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=2026-01-14&endDate=2026-01-15&adults=2®ionId=11584) ![This was a great local spot for snorkeling and much less crowded than the main beaches. You literally park alongside the road at mile marker 14 and walk out onto the beach. Close to shore the water is a little cloudy but if you swim about 50 yards out, the depth increases to about 15 feet and you have clear views of some amazing fish 🐠🐟](https://images.trvl-media.com/place/11584/d420d434-6dd4-421e-91de-078fdbd219b9.jpg?impolicy=fcrop&w=899&h=675&p=1&q=high) Photo by Rachel Elyse ## Top Olowalu Hotel Reviews ![Fairmont Kea Lani Maui](https://images.trvl-media.com/lodging/1000000/10000/8800/8765/98cd34a1_y.jpg) ### Fairmont Kea Lani Maui 10/10 Excellent "Spotless room, turn down service at night. Fantastic stay " [](https://expedia.ca/Kihei-Hotels-Fairmont-Kea-Lani-Maui.h8765.Hotel-Information) ![The Ritz-Carlton Maui, Kapalua](https://images.trvl-media.com/lodging/1000000/10000/3400/3390/w3996h2667x0y0-f44bed53_y.jpg) ### The Ritz-Carlton Maui, Kapalua 10/10 Excellent "Yes " [](https://expedia.ca/Lahaina-Hotels-The-Ritz-Carlton-Maui.h3390.Hotel-Information) ![Grand Wailea Maui, A Waldorf Astoria Resort](https://images.trvl-media.com/lodging/1000000/10000/7900/7867/w3840h2556x0y3-29570997_y.jpg) ### Grand Wailea Maui, A Waldorf Astoria Resort 10/10 Excellent "Very nice resort for a family vacation!" [](https://expedia.ca/Kihei-Hotels-Grand-Wailea-Maui.h7867.Hotel-Information) ![Four Seasons Resort Maui at Wailea](https://images.trvl-media.com/lodging/1000000/20000/14400/14336/ed7cc193_y.jpg) ### Four Seasons Resort Maui at Wailea 10/10 Excellent "Always exceptional " [](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? > - Search for the lowest price per night from CA $649 ### What makes a hotel 5 stars in Olowalu? ### Are there any 5-star all-inclusive resorts in Olowalu? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [1 Star Hotels in Maui ](https://www.expedia.ca/1Star-Maui-Hotels.s10-0-d180073.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Kahului ](https://www.expedia.ca/2Star-Kahului-Hotels.s20-0-d2646.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Kihei ](https://www.expedia.ca/2Star-Kihei-Hotels.s20-0-d9304.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Kuau ](https://www.expedia.ca/2Star-Kuau-Hotels.s20-0-d553248635975748672.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Lahaina ](https://www.expedia.ca/2Star-Lahaina-Hotels.s20-0-d8499.Travel-Guide-Filter-Hotels) - 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