Find hotels with pools in Wailea, Kihei from $519

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Pick from 50 Wailea Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Wailea Beach Villas
2 outdoor pools, free cabanas, pool umbrellas
Wailea Beach Villas
4.5 star property
9.8 out of 10, Exceptional, 154 reviews
"Incredible! Excellent from start to finish!"
Wailea Beach Villas
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
View from property
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
9.8 out of 10, Exceptional, 159 reviews
"Fabulous panoramic view, comfortable accommodations, well appointed condo, everything you could possibly need in the kitchen. Beautiful Lanai setting & comfortable furnishings. Dave was very responsive throughout our planning & while we were in the condo. Sure hope we get to come back some day. This is a keeper condo/vacation. Mahalo!"
The price is $275
$629 total
includes taxes & fees
Jun 17 - Jun 18
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
Four Seasons Resort Maui at Wailea
Club Suite, 1 Bedroom | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Four Seasons Resort Maui at Wailea
5.0 star property
9.6 out of 10, Exceptional, 1,001 reviews
"Great service, great place! "
The price is $995
$1,174 total
includes taxes & fees
Jun 7 - Jun 8
Four Seasons Resort Maui at Wailea
Luxurious Wailea Ekahi 45D! Close to Pools & Beach. 25 miles from fire area.
Beach nearby, sun loungers, beach towels
Luxurious Wailea Ekahi 45D! Close to Pools & Beach. 25 miles from fire area.
9.6 out of 10, Exceptional, 79 reviews
"This unit exceeded our expectations! Everything we wanted or needed was there and the property was beautiful! Although we were in one of the condos farthest from the ocean, it didn’t matter! Views were amazing and walk was easy! I would highly recommend this property and hope to return again soon!!"
Luxurious Wailea Ekahi 45D! Close to Pools & Beach. 25 miles from fire area.
Wailea Elua- CoralTree Residence Collection
2 outdoor pools
Wailea Elua- CoralTree Residence Collection
3.5 star property
9.6 out of 10, Exceptional, 237 reviews
"Enjoyed my stay."
Wailea Elua- CoralTree Residence Collection
Ho‘olei Villas at Grand Wailea
Outdoor pool, sun loungers
Ho‘olei Villas at Grand Wailea
5.0 star property
9.6 out of 10, Exceptional, 36 reviews
"This is an amazing place to stay with a family. Views. Facilities. Local entertainment, dining, shopping, and activities."
The price is $2,155
$2,601 total
includes taxes & fees
Jun 3 - Jun 4
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui
View from room
Fairmont Kea Lani Maui
4.5 star property
9.4 out of 10, Exceptional, 1,001 reviews
"Easily some of the best service at any resort we’ve ever stayed. Start to finish everyone was fantastic. Front desk. Valet. Pool. Restaurants. Everyone went above and beyond. Will definitely return. "
The price is $807
$1,011 total
includes taxes & fees
Jun 4 - Jun 5
Fairmont Kea Lani Maui
Hotel Wailea, Relais & Chateaux - Adults Only
Outdoor spa tub
Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
9.4 out of 10, Exceptional, 952 reviews
"A truly beautiful property! The staff was all super friendly and accommodating. The rooms are spacious and comfortable. They threw in dozens of “little touches” to make us feel welcomed and appreciated. Highly recommended. By far the nicest place I’ve ever stayed!"
The price is $899
$1,108 total
includes taxes & fees
Jun 2 - Jun 3
Hotel Wailea, Relais & Chateaux - Adults Only
Andaz Maui at Wailea Resort - a concept by Hyatt
5 outdoor pools, cabanas (surcharge), pool umbrellas
Andaz Maui at Wailea Resort - a concept by Hyatt
4.5 star property
9.2 out of 10, Wonderful, 1,001 reviews
"Absolutely loved our stay at the Andaz!!! One thing we did not enjoy was that it was $50/day for parking which we were not expecting. Breakfast was also $50/day (per person) along with a $50/day resort fee. Seemed like there wasn't much included in the price of the hotel. Overall, a stunning hotel and great service but we will these prices were a little more clear when booking."
The price is $854
$1,066 total
includes taxes & fees
Jun 2 - Jun 3
Andaz Maui at Wailea Resort - a concept by Hyatt
Residence Inn by Marriott Maui Wailea
Property amenity
Residence Inn by Marriott Maui Wailea
3.5 star property
9.2 out of 10, Wonderful, 927 reviews
"Great place to stay! It exceeded our expectations! We will definitely be coming back!"
The price is $519
$612 total
includes taxes & fees
Jun 15 - Jun 16
Residence Inn by Marriott Maui Wailea
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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.

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Price trends for hotels in Wailea

Less expensive
More expensive
This month
Next month
August
January
$349
$375
Month
Price
January
$755
February
$491
March
$440
April
$449
May
$399
June
$349
July
$375
August
$345
September
$367
October
$401
November
$486
December
$425
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.

Wailea Hotels with a Pool information

 

Hotels with a Pool in Wailea

50

Highest price
$995
Cheapest price
$519
Number of guest reviews
8,291
Total number of hotels in Wailea
1,150

 

Frequently asked questions

What's it like visiting Wailea?
If lounging by a pool is your idea of the perfect getaway, you might want to think about romantic Wailea, which has 6 places to stay with pools. During your trip, you can explore sights such as Shops at Wailea and Ulua Beach, and then kick back and relax poolside at one of the accommodations in Wailea that guests like for their pools.
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 5 restaurants. Fairmont Kea Lani Maui: Resort, 11-minute walk from Wailea Beach. Offers 3 outdoor pools, a children’s pool, and 4 restaurants. Andaz Maui at Wailea Resort - a concept by Hyatt: Resort located near Wailea Beach. Provides 4 restaurants, 5 outdoor pools, and 2 pool bars. Hotel Wailea, Relais & Chateaux - Adults Only: Resort located near Wailea Beach. Features 3 restaurants, an outdoor pool, and a full-service spa. Fairmont Kea Lani Maui Villa Experience: Resort, 12-minute walk from Wailea Beach. Offers 3 outdoor pools, a children’s pool, and 4 restaurants.
How many pool hotels will I find in Wailea?
Expedia has 6 hotels in Wailea for your poolside break.
What is there to see and do in Wailea?
Spend some time experiencing the great outdoors at Ulua Beach and Wailea Beach. During your stay, check out sights such as Shops at Wailea, Polo Beach, and Keawakapu Beach North. Visitors to Wailea speak highly of the natural attractions, including the beautiful beaches.

Recent reviews of Wailea hotels
Expedia verified reviews

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5/5 Excellent
"The hotel was above expectation. "
A verified traveler stayed at Wailea Beach Resort - Marriott, Maui
Posted 2 days ago
Wailea Beach Resort - Marriott, Maui