Find Hotels with a Pool in Wailea, HI from CA $814

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Wailea Hotels with a Pool

This weekend
Next weekend

Our top choices for Wailea hotels with a pool

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Splash into paradise at this beachfront resort with 3 outdoor pools, a swim-up bar, and a thrilling waterslide.
The price is CA $1,061
CA $1,260 total
includes taxes & fees
Apr 30 - May 1
Four Seasons Resort Maui at Wailea

Grand Champions

Grand Champions
2.5 star property
Wailea
9.0 out of 10, Wonderful, (4 reviews)
  • cleanliness
    Wailea resort offers serenity with sun-drenched pool and hot tub, perfectly situated by golf greens.
The price is CA $165
CA $929 total
includes taxes & fees
Apr 23 - Apr 24
Grand Champions

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Plunge into luxury at this adults-only resort with a serene outdoor pool and beach shuttle service.
The price is CA $1,317
CA $1,646 total
includes taxes & fees
Apr 21 - Apr 22
Hotel Wailea, Relais & Chateaux - Adults Only

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
4.5 star property
Wailea
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into paradise at this Hawaiian resort with 4 outdoor pools, a waterslide, and poolside cocktail service.
The price is CA $1,136
CA $1,446 total
includes taxes & fees
Apr 22 - Apr 23
Wailea Beach Resort - Marriott, Maui

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
Wailea
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Splashy paradise with 9 pools, a lazy river, and oceanfront views awaits at this luxury Hawaiian resort.
The price is CA $960
CA $1,230 total
includes taxes & fees
Apr 16 - Apr 17
Grand Wailea Maui, A Waldorf Astoria Resort

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,002 reviews)
  • cleanliness
    Triple the tropical fun with 3 outdoor pools, cabanas, and a swim-up bar at this Hawaiian beachfront haven.
The price is CA $1,553
CA $1,926 total
includes taxes & fees
May 2 - May 3
Fairmont Kea Lani Maui

Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt
4.5 star property
Wailea
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Discover coastal luxury with 5 ocean-view pools where cabanas and loungers invite blissful relaxation beneath the Hawaiian sun.
The price is CA $1,318
CA $1,647 total
includes taxes & fees
Apr 16 - Apr 17
Andaz Maui at Wailea Resort - a concept by Hyatt

Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea
3.5 star property
Wailea
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Soak up the sun at this peaceful poolside oasis with free cabanas, hot tub, and just steps from Wailea Beach.
The price is CA $685
CA $814 total
includes taxes & fees
Apr 15 - Apr 16
Residence Inn by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea
4.0 star property
Wailea
9.2 out of 10, Wonderful, (232 reviews)
  • cleanliness
    Dive into Maui's magical poolside paradise with mountain views and sunset cocktails.
The price is CA $685
CA $855 total
includes taxes & fees
Apr 15 - Apr 16
AC Hotel by Marriott Maui Wailea

225USD 4-4 thru 4-7 Reno 10-2025 Sunrise & Sunset Bose Bidets Walk to Pool GEM

225USD 4-4 thru 4-7 Reno 10-2025 Sunrise & Sunset Bose Bidets Walk to Pool GEM
Wailea
9.8 out of 10, Exceptional, (183 reviews)
The price is CA $433
CA $972 total
includes taxes & fees
Apr 14 - Apr 15
225USD 4-4 thru 4-7 Reno 10-2025 Sunrise & Sunset Bose Bidets Walk to Pool GEM
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.

Choose what matters most at hotels with a pool in Wailea

Price trends for hotels in Wailea

Less expensive
More expensive
This month
Next month
April
January
CA $442
CA $576
Month
Price
January
CA $916
February
CA $556
March
CA $749
April
CA $442
May
CA $576
June
CA $463
July
CA $468
August
CA $450
September
CA $595
October
CA $609
November
CA $508
December
CA $659
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Wailea. Select dates and complete search for nightly totals inclusive of taxes and fees.

Top Wailea Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Wailea?
Grand Wailea Maui, A Waldorf Astoria Resort: Resort, 9-minute walk from Wailea Beach. Features 9 outdoor pools, a children's pool, and a lazy river. Four Seasons Resort Maui at Wailea: Resort, 6-minute walk from Wailea Beach. Offers 3 outdoor pools, a children's pool, and 3 restaurants. Fairmont Kea Lani Maui: Resort, 11-minute walk from Wailea Beach. Provides 3 outdoor pools, a children's pool, and 6 restaurants. Wailea Beach Resort - Marriott, Maui: Resort, 10-minute walk from Wailea Beach. Features 4 outdoor pools, a children's pool, and 4 restaurants. Andaz Maui at Wailea Resort - a concept by Hyatt: Resort located near Wailea Beach. Offers 4 restaurants, 5 outdoor pools, and 2 pool bars.
What is there to see and do in Wailea?
Explore places like Wailea Beach while you're in Wailea. Surround yourself with nature at Ulua Beach and Polo Beach. Visitors to Wailea speak highly of the natural attractions, including the beautiful beaches.

Explore a world of travel with Expedia