An aerial view of a coastal town with clear turquoise waters, two prominent islands, and lush green hills.

Find Hotels with a Pool in Kailua, HI from CA $296

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Check availability on Kailua Hotels with a Pool

Tonight
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Kailua hotels with a pool

1. Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center
Makawao
  • Swim and stretch in paradise at this serene retreat, where an outdoor pool meets lush gardens and wellness activities await you.
CA $413
CA $606 total
includes taxes & fees
Sep 20 - Sep 21
Lumeria Maui Educational Retreat Center

2. Maui Beach Hotel

Maui Beach Hotel
Kahului
  • Pool paradise meets island escape at this hotel's sun-drenched oasis just steps from the beach.
CA $221
CA $296 total
includes taxes & fees
Sep 26 - Sep 27
Maui Beach Hotel

3. Maui Seaside Hotel

Maui Seaside Hotel
Kahului
  • Outdoor island pool haven offers steps-to-beach luxury with volcano views and fire pits.
CA $251
CA $339 total
includes taxes & fees
Oct 1 - Oct 2
Maui Seaside Hotel

4. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
CA $2,008
CA $4,062 total
includes taxes & fees
Oct 7 - Oct 8
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

5. Courtyard Maui Kahului Airport

Courtyard Maui Kahului Airport
Kahului
  • Splash into sunshine at this hotel's tropical pool oasis, where loungers and umbrellas await your relaxation.
CA $474
CA $563 total
includes taxes & fees
Oct 6 - Oct 7
Courtyard Maui Kahului Airport

6. Kohea Kai Hotel Maui

Kohea Kai Hotel Maui
North Kihei
  • Tropical pool oasis minutes from Kamaole Beach with sun loungers and ocean adventure possibilities.
CA $237
CA $322 total
includes taxes & fees
Sep 24 - Sep 25
Kohea Kai Hotel Maui

7. Resort Condo near the Beach

Resort Condo near the Beach
North Kihei
Resort Condo near the Beach

8. Maui Coast Hotel

Maui Coast Hotel
South Kihei
  • Poolside luxury awaits at this Maui resort with 2 outdoor pools, 3 hot tubs, and cabana service for ultimate relaxation.
CA $290
CA $409 total
includes taxes & fees
Sep 27 - Sep 28
Maui Coast Hotel

9. SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
North Kihei
  • Refreshing ocean views complement this Kihei oceanfront retreat with heated pool and hot tub near the beach.
CA $200
CA $651 total
includes taxes & fees
Sep 19 - Sep 20
SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

10. Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas
North Kihei
  • Splash into paradise with a beachside pool oasis featuring free cabanas at this family-friendly Maui retreat.
CA $447
CA $580 total
includes taxes & fees
Oct 17 - Oct 18
Hilton Grand Vacations Club Maui Bay Villas
View all properties

Choose what matters most at hotels with a pool in Kailua

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Kailua Hotel Reviews

Kohea Kai Hotel Maui

Kohea Kai Hotel Maui

8/10 Good
"If planning practical trips this the place to stay . They have utensils, cookware, stove and microwave inside rooms. Just need to be better emptying trash in recreation areas."
Nadilyn 6-night trip
Posted 1 day ago
Kohea Kai Hotel Maui
Maui Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"When I go to Calee, I stay in this hotel 100% of the time. I’ve probably been here about a dozen times over the past few years the property is clean and the staff is always great. Tantes is the restaurant on site and is wonderful. Highly recommend both."
Robert 1-night trip
Posted 1 day ago
Maui Seaside Hotel
Maui Schooner Resort

Maui Schooner Resort

10/10 Excellent
"Cool"
Maryna 11-night trip
Posted 8 days ago
Maui Schooner Resort
Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

10/10 Excellent
"This is a beautiful, quiet, and relaxing place to stay that offers a nice breakfast and lovely grounds with pool, jacuzzi, fire pits, and comfortable outdoor furniture. There’s a schedule of a variety of yoga classes over a week and areas conducive to meditation. That said, we never saw staff around other than at check-in and breakfast and wonder if they’re short on employees. We didn’t receive any room service over our 5 night stay, nor did we ask, and the beautifully designed grounds needed weeding. Those shortcomings didn’t diminish our experience and we do recommend it for what it does offer and for its location. Perhaps Lumeria was and could again be a jewel. It has such good bones and with a bit of attention and management could be exceptional."
Debbie 5-night trip
Posted 10 days ago
Lumeria Maui Educational Retreat Center
Paia Inn

Paia Inn

10/10 Excellent
"Lovely relaxed place, “shabby chic” and priced correctly. We loved the space, and the environment especially the quiet beach side area. Perfect location for Paia bars and shops."
Jan 3-night trip
Posted 11 days ago
Paia Inn
Sugar Beach Resort - Maui Condo & Home

Sugar Beach Resort - Maui Condo & Home

10/10 Excellent
"The property and condo were extremely clean and well maintained."
Pamela Dee 7-night trip
Posted 2 months ago
Sugar Beach Resort - Maui Condo & Home

Frequently asked questions

What are some accommodations with pools in Kailua?
Maui Coast Hotel: Hotel located near Wailea Beach. Features 2 outdoor pools, a children's pool, and 2 restaurants. Maui Seaside Hotel: Offers complimentary wireless internet access, an outdoor pool, and flat-screen televisions. Maui Beach Hotel: Provides a 24-hour fitness center, an outdoor pool, and LED televisions. Courtyard Maui Kahului Airport: Features a snack bar/deli, an outdoor pool, and a 24-hour fitness center. Hilton Grand Vacations Club Maui Bay Villas: Offers a children's pool, an outdoor pool, and a snack bar/deli.
What is there to see and do in Kailua?
Explore places like Haleakala National Park while you're in the area. Make a point to visit attractions like Hoʻokipa Beach Park and Maui Garden Of Eden - Botanical Gardens & Arboretum.
When is the best time to book a hotel with a pool in Kailua?
Taking into account the local weather in Kailua is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and September with an average temp of 75°F, while the coldest months are March and February with an average of 71°F. Average annual precipitation for Kailua is 40 inches.

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