
Holiday rentals with a pool in Kaanapali
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Top-rated rentals with a pool in Kaanapali
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Spectacular views, prime location Kapalua, Maui.
Stylish, romantic two-level villa enjoying spectacular direct views of the Ocean. Relax and rejuvenate on the upstairs BR private lanai or the ground floor patio both are ideal for viewing the stellar coastal landscape. Start the day by watching the sunrise over the ocean from the comfort of your luxurious California King bed. Walking distance to everything that makes Kapalua Resort a special, magical and unforgettable place. A/C units on both levels. Kapalua is unaffected by the Lahaina fire

MauiKai 405 - Oceanfront Bliss!!
Maui Gov’t Approved Short Term Rental - Hotel District- Amazing direct beach access from the building. Panoramic view of the Ocean and has everything you need for a dream vacation for a family of 4. King bed and two pullout sofa beds in the condo. Over 900 sq ft of living space with an oceanview lanai for dinners or viewing the whales play. Central AC with fully stocked kitchen. 75” Large screen TV with Sonos sound system with full cable, Netflix, NHL TV. Exercise bike on lanai. Fast internet!

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.

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.

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.

Honu Hideaway, Maui Kaanapali Oceanfront Penthouse
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 top 10th 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

Mahana 1015 - Luxury Oceanfront Condo (1bd/2ba)
Welcome to Mahana 1015, a breathtaking oceanfront condo located on one of the top floors of the exclusive Aston Mahana at Ka’anapali Resort. Offering two full bathrooms and spacious accommodations, this one-bedroom suite is the perfect place to indulge in Maui’s natural beauty with unmatched comfort and style.
Popular amenities for Kaanapali rentals with a pool
House rentals with a pool

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

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!

Cozy Beach Bungalow +Bikes & Pickleball Gear

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

Ocean Views- Beachfront- Steps to a Sandy Beach!

Crazy Good Deal Eldorado Beach Resort Ka'anapali

Oceanfront Getaway, Brand New, Steps To Beach

Beautiful Papakea 1 Bedroom with A/C

Oceanfront Kahana Reef Condo

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Panoramic Views right on a Sandy Swimmable Beach

Stunning Oceanfront, Sunset and Marine Life Views
Other holiday rentals with a pool

Maui Beach Frt Condo w/ AC Kaanapali Shores Resort

Oceanfront penthouse - stunning view!

Oceanfront King Bed Renovated Maui Kai Condo MK806

180* Oceanfront View w/ AC! Remodel+2Pools+Clean

Charming Kaanapali cottage with ocean view

Papakea Fall Sale - Best Location in Complex

Stunning Maui Villa

Aloha! 10 Steps to Ocean. Breathtaking Ocean Front
Quick stats about holiday rentals with a pool in Kaanapali
Total rentals
3.8K properties
Total number of reviews
38K reviews
Family-friendly rentals
1.8K properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
2.3K properties have a dedicated workspace
Wifi availability
3.8K properties include access to wifi
Destinations to explore
- Rentals with a washing machine and dryer Kaanapali
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- Maui
- Kaanapali Beach
- Kahului Beach
- Kepuhi Beach
- Lahaina Beach
- Honolua Bay
- Sandy Beach
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Manele Golf Course
- Kalani Beach
- Maui Ocean Center
- Wailea Beach
- Hāmoa Beach
- Oneloa Beach
- Kaipukaihina
- Puu Olai Beach
- Changs Beach
- Palauea Beach
- Old Lahaina Luau
- Wailau Valley
- Polo Beach
- Wailea Golf Club