What are the top rated Cottage Rentals in Wailea?

There are a lot of options in Wailea. If you plan on staying in the Wailea area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Wailea: <a href="/property/romantic-luxury-sensual-retreat-couples-only/HA-1213564788" class="class="static-page-link"">Romantic, Luxury, Sensual Retreat - Couples Only</a> <a href="/property/ekahi-34f-best-panoramic-ocean-view/HA-3211833116" class="class="static-page-link"">Ekahi 34F - Best Panoramic Ocean View!</a> <a href="/property/wailea-custom-home-pool-panoramic-ocean-view-waterfalls-maui-ocean-palms/HA-321502088" class="class="static-page-link"">Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms</a> <a href="/property/aloha-kai-suite-at-wailea-beach-villas-penthouse-205-ocean-view-3-br-3-ba/HA-321122885" class="class="static-page-link"">Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA</a> <a href="/property/owner-direct-check-our-160-reviews-elua-village-701-luxury-2br-ocean-view/HA-121212306" class="class="static-page-link"">Owner Direct - Check our 160 Reviews! - Elua Village 701, Luxury 2BR, Ocean View</a> <a href="/property/georgeous-5-star-wailea-retreat-tranquil-corner-unit-top-tier-upgrades/HA-3211746792" class="class="static-page-link"">🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈</a> <a href="/property/luxe-townhome-ocean-views-relax-by-the-pool/HA-321223642" class="class="static-page-link"">Luxe Townhome, Ocean Views, Relax by the Pool</a> <a href="/property/featured-on-a-e-s-vacation-rental-potential-luxury-family-condo-ac-and-pool/HA-3211331969" class="class="static-page-link"">Featured on A&amp;E&#39;s Vacation Rental Potential! Luxury Family Condo! AC and Pool!</a> <a href="/property/nnew-kitchen-remodel-amazing-view/HA-321456792" class="class="static-page-link"">nNEW KITCHEN REMODEL! Amazing View!</a> <a href="/property/125-5star-reviews-says-it-all-all-upgraded-vaulted-ceil-golf-ocean-view/HA-3212379983" class="class="static-page-link"">125+ 5star REVIEWS SAYS IT ALL! All upgraded/vaulted ceil/Golf &amp; Ocean view!</a>

How much does it cost to rent a cottage in Wailea?

The average cost for a cottage rental in Wailea is $648 per night. Smartours has a wide list of great cottages near Wailea that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Wailea that allow pets?

Yes, here are the top cottage rentals in Wailea that allow you to bring your pet: Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted Luxury Cottage w/Private Pool. Under The Warm Maui Sun Pmt #BBKM20160004 Private Ocean View Cottage Overlooking Wailea Amazing view, Close to the beach, Wailea Ekahi Unit 20i Ho'olei at Grand Wailea Luxurious Wailea Ocean Vistas F207 Spectacular Ocean Views - Beautifully Renovated Condo - 2 New Pools <a href="/all/usa/hawaii/kihei/wailea" class="class="static-page-link"">See all pet-friendly vacation rentals in Wailea on Smartours</a>

Do you have any rental cottages in Wailea that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Wailea to find one that works for you.

Are there quality cottages in Wailea that have indoor swimming pools?

As of 2026, the data from Smartours shows that there are Over 6 private swimming pools or cottages with indoor pools in the Wailea area along with other great amenities.

Cottages in Wailea [2025/2026] Smartours

Hawaiian Cottage and Personal Paradise/BBKM 2013/0004

From US $1,012

10.0 (200 Reviews)

Cottage

Hawaiian Cottage and Personal Paradise/BBKM 2013/0004

Air Conditioner
Parking
Pool

Cottages in Wailea

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