
Holiday rentals with a pool in Kaanapali
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kaanapali
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Ka'anapali Oceanfront Dream-view Retreat with AC!
This serene oceanfront retreat is located along the Kaanapali coast, less than 50' from the beach and waves. The unit offers a whole lot of Aloha, with unobstructed views of an expansive crystal blue/green ocean, crashing waves, swaying palm trees, adjacent islands, starry skies and sea life (sea turtles and monk seals all year long, migrating humpback whales from late Dec through April). The interior is clean, nicely appointed, & has lots of amenities to make your stay comfortable & enjoyable.

NEWLY REMODELED OCEAN VIEW CONDO, STEPS FROM BEACH
Your next relaxing Lahaina escape awaits at this stunning 1-bedroom, 2-bath vacation rental condo - steps away from Kapalua Bay Beach & centrally located next to the Montage Resort. Your group of up to 6 guests will love returning to the comfort of this home, offering over 1,100 sq ft of living space. With easy access to championship golf courses, fine dining, walking/hiking paths, shopping, spas, & several bays/beaches great for snorkeling, surfing, & relaxing, this is the perfect home base.

Kaanapali Cottage ICC 29 Indoor/Outdoor Living
International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi
Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The owner’s spared no expense in renovating this unit making it hand’s down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

Ka Hale Aloha (The Love Shack)
Escape and fall in love with “Ka Hale Aloha-The Love Shack” where paradise awaits you....This adventurous hideaway will leave you feeling refreshed, relaxed and more alive than ever before!! Experience all the life & Aloha the island of Maui has to offer in your private detached bungalow located on an old 8 acre fruit plantation turned condos, just steps from the ocean. This is a unique experience...there’s nothing quite like "Ka Hale Aloha" on island * Check us out on IG at @kahalealoha

Absolutely Oceanfront - Corner Unit- Amazing Views
Absolutely Best Direct Ocean Front With Unobstructed Views if Molokai and Lanai Not from the side of a building or overlooking other units - Deluxe Corner High Floor Apartment - Additional Side Window - Plus Bedroom and Bathroom View Windows - Guests tell us the views from our high floor apartment is better than whale watching tours - Closest building to the Ocean on Maui - Memory Foam King Bed (not Queen) - No Bedbugs here/Bed Bug Protective King Mattress and pillow covers.

Ocean's Edge Romance: Sunsets, Whales, Views!
Bask as you wake to the sound of the waves crashing below and the sight of pristine turquoise water and expansive rainbows. You may pinch yourself as you take it all in, thinking you are still dreaming. We are excited to be able to offer Maui Kai 807, a studio condo in the original beach front high-rise on Maui's west side. No other resort in Kaanapli will put you closer to the ocean's edge. Enjoy the sights of sunsets, turtles, dolphins, and whales (Dec-March) right from your lanai.

Kapalua, luxe, ocean view, beach, spa, golf/tennis
KAPALUA - Best location! Welcome to the luxuriously Kapalua Bay Villa #37B1. Bright and airy, with comfortable furniture and modern appliances. Scenic ocean view, a 5-minute walk to Kapalua Bay, Montage Resort, tennis, golf, hiking, zip-lining, amazing restaurants, and a first-class spa. Kapalua Bay Villas is a low-density community within the Kapalua Resort—a 15-minute drive to Kaanapali, and a 40-minute drive to Central Maui to explore the island.

Beautiful Ocean View on Quiet Side of Honua Kai!
*** NO RESORT OR PARKING FEES! *** Honua Kai is a Four Star resort with four pools, five spas, a fitness center, Aina Gourmet Market, and beachfront Dukes Restaurant on premises. Our one bedroom condo has a partial ocean view from the lanai, has a KING sized bed in the bedroom AND queen SOFA SLEEPER for additional guests. We stock our condo with four beach chairs, umbrella, two coolers, boogie boards, and pool toys for you to use.

DIRECT OCEAN FRONT STUDIO W OCEAN IS UR BACK YARD!
This is a hotel-zoned condo. It will not be affected by potential upcoming county regulations. Book with confidence!! Thank you for considering my direct ocean front studio condo in Kahana, my condo is located minutes outside of Lahaina , Kaanapali , Napili and Kapalua. You'll find the ocean view from my lanai/ room to be breathtaking and serene. This is truly an hidden gem on Maui.

Stylish Love Hideaway, Maui Kaanapali Oceanfront
Oceanfront studio in one of a kind boutique condominium, on world famous Kaanapali Beach. Wake up to a breathtaking oceanview, take it all in from spacious lanai, fall asleep to the sound of the ocean every night Located on the 3rd floor with close touch to ocean breeze and fantastic views, easy access to world-class beaches, restaurants, shopping and golfing

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt
Spectacular Ocean & Outer Island views from your Air Conditioned condo! Enjoy snorkeling with Sea Turtles in your backyard, seasonal Whale Watching from your kitchen, and breathtaking Sunsets... Welcome to Paradise! Traveling with family or friends? Please see our other listing just few doors down: Oceanfront Oasis! Sea Turtle Cove B17 Napili Point
Popular amenities for Kaanapali rentals with a pool
House rentals with a pool

Mahalo Pono @ Ka 'anapali Royal

Newly Remodeled Cottage

Wake Up to Sweeping Ocean Views in Platinum Style

Stunning ocean view, heated pool at home by Wailea

Kula Jewel - Pool, Hot Tub & Awesome Views!

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Beach Bungalow w/ Cruiser Bikes & Pickleball!

#1 Kaanapali Beach C101 Maui Eldorado, Sleeps 3.
Apartment rentals with a pool

Oceanfront | Luxury View | 2 Beds

MAHANA 505 OCEAN FRONT W/ SPECTACULAR VIEWS

Beautiful Papakea 1 Bedroom with A/C

Oceanview Maui Condo, Turtles, Whales, Rainbows

TOP FLOOR!!!! Oceanfront, free Wi-Fi, free parking

Panoramic Views right on a Sandy Swimmable Beach

Napili bay Studio November special$99

Sunsets and Turtles and Whales, Oh My!
Other holiday rentals with a pool

Aloha Always- King Suite, Endless Ocean Views, wAC

Maui Beach Frt Condo w/ AC Kaanapali Shores Resort

Oceanfront penthouse - stunning view!

Turtles & Tales: Luxe Beachfront w/AC & Ocean view

HONUA KAI Largest 1bd Ocean View Closest to Ocean!

New Remodel Oceanfront Sunset Paradise

Stunning Maui Villa

XMas SALE-AC Beachfront Maui Gem – Panoramic Views
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $535 SGD | $554 SGD | $588 SGD | $586 SGD | $520 SGD | $674 SGD | $688 SGD | $683 SGD | $520 SGD | $423 SGD | $445 SGD | $527 SGD |
| Avg. temp | 23°C | 23°C | 23°C | 24°C | 25°C | 26°C | 27°C | 27°C | 27°C | 26°C | 25°C | 24°C |
Quick stats about holiday rentals with a pool in Kaanapali

Total holiday rentals
Explore 4,030 holiday rentals in Kaanapali

Verified guest reviews
Over 40,850 verified reviews to help you choose

Family-friendly holiday rentals
1,860 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
2,600 properties have a dedicated workspace

Wifi availability
4,000 of Kaanapali holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kaanapali rentals

4.8 Average rating
Kaanapali stays are highly rated by guests – averaging 4.8 out of 5!
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- Maui
- Kaanapali Beach
- Kahului Beach
- Kepuhi Beach
- Lahaina Beach
- Laie
- Honolua Bay
- Sandy Beach
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Manele Golf Course
- Kalani Beach
- Maui Ocean Center
- Wailea Beach
- Hāmoa Beach
- Kaupoa Beach
- Kaipukaihina
- Puu Olai Beach
- Palauea Beach
- Kapua
- Changs Beach
- Wailau Valley
- Old Lahaina Luau




