When is the best time to visit Maui, HI?

Maui is most affordable and least crowded in the shoulder seasons, late spring (April-May) and early fall (September-October). Summer is peak for beach activity but rates are 30-60% higher. Off-season (November-March) offers the quietest stays and sometimes the most character.

How are the waterfront rentals in Maui chosen?

Each property in Maui is hand-picked for genuine waterfront access, not water view, not a short walk from the beach, but doors-to-water. Listings are selected from public booking platforms (Vrbo, Airbnb, Booking.com, Whimstay) for genuine waterfront access and accurate location. Rates are set by the host and visible at the booking link.

Are the properties on SleepByTheBeach available on Vrbo or Airbnb?

Yes, each property links directly to its listing on Vrbo, Airbnb, Booking.com, Whimstay, or the host's own booking system. We curate from public listings; we don't own or manage these properties. We may earn a small commission when you book through our affiliate links at no cost to you.

What makes Maui different from other beach towns?

Resort beaches down the west and south shores, from Kapalua and Kaanapali to Wailea.. It has the character of a small coastal town without the density of major resort destinations. Our curation focuses on quiet, authentic stays within walking distance of the water.

Maui

Resort beaches down the west and south shores, from Kapalua and Kaanapali to Wailea.

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6423 waterfront rentals·30 shores·Every listing on the water·Updated 2026-11-12

Most of Maui's rentals sit on two dry, sunny coasts. West Maui runs from Kapalua through Napili, Honokowai and Kaanapali to Lahaina, with condos set right behind small sandy bays and a view across the channel to Lanai and Molokai. South Maui runs from Maalaea through Kihei to Wailea, where the beaches are wider and a paved path links the resorts. Humpback whales winter in the channel between the islands, and from December to April you can often watch them from a lanai.

StateHI

Peak seasonDecember to March

Best forWaterfront stays

Featured242 rentals

The curated list · 242 rentals

Where we would stay in Maui.

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Sleeps

Shore

Nightly rates are the ones each partner listed when we last read them. The partner gives the final price for your dates. A rental with no rate shown is left out of the price filters.

No. 241

Stunning Ocean Views and Modern Comforts - Charming Beachfront Retreat

Condo

sleeps 4 private pool about $496 a night

Welcome to your beachfront retreat! Our cozy studio condo, situated directly on the picturesque Napili Bay Beach, offers stunning ocean views and modern comforts for your ideal Maui getaway. Recently renovated with a fully equipped kitchen, a comfortable queen-size bed, and an additional trundle bed, our condo ensures a relaxing stay for couples or small families. Step outside onto the soft sands and crystal-clear waters of Napili Bay Beach, perfect for swimming, snorkeling, or sunbathing. Convenient extras include communal gas grills, picnic tables, and a coin-operated laundry facility. Your Maui escape begins here - book today!

Check rates on Whimstay →

No. 242

Island Oasis Near Kaanapali Beach & Black Rock

Entire condo

2 bedroom sleeps 6 private pool about $497 a night

A slice of paradise awaits at this West Maui vacation rental in Maui Eldorado Resort! This 2-bedroom, 2-bath Kaanapali condo has an authentic Hawaiian theme with easy access to Ka’anapali Beach and Black Rock, making it the perfect place to create unforgettable memories. Shop at Whalers Village, tee off at the famous Ka’anapali Golf Courses, or explore the colorful reefs while snorkeling. The resort has 3 outdoor pools, a hot tub, a fitness center, community beachfront cabanas, and more! more! The space Transient Accommodations Tax License TA- -01. General Excise Tax License GE- -01. Resort Perks. Family Friendly. Garden View. Private Beach Access Bedroom 1: California King Bed.

Check rates on Whimstay →

Search every stay in Maui on Booking.com

Hotels, beach houses, apartments, and resorts. Free cancellation on most rooms. Then add a flight in or a rental car for dune drives.

Search stays → Flights to Maui Car rental

Or browse the same coast on Vrbo: Browse Vrbo →

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Curated luxury alternative

Prefer a boutique hotel or villa?

If a hand-picked, design-led hotel sounds better than a vacation rental, Skylark Travel Group covers the same destinations with curated boutique stays, Mr & Mrs Smith, exclusive deals, real human concierge.