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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.

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Top Guest favourite
Condo in Lahaina
4.94 out of 5 average rating, 130 reviews

Oceanfront Two Bedroom at Kaanapali Shores #504

Enjoy oceanfront views from this 5th floor 2-bedroom / 2-bath condo at the popular Kaanapali Shores Resort. Central A/C, spacious living room, washer/dryer, full kitchen, wifi, cable tv & SNES classic Just steps away from the ocean Watch beautiful sunsets from the resort The resort has pools, hot tubs, restaurant and bar, and more Supermarket across the street *Wildfire Update* This condo is located in North Kaanapali outside the Lahaina wildfire burn zone. West Maui is now open to visitors

Top Guest favourite
Condo in Lahaina
4.97 out of 5 average rating, 238 reviews

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.

Top Guest favourite
Condo in Lahaina
4.99 out of 5 average rating, 138 reviews

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.

Top Guest favourite
Condo in Lahaina
4.99 out of 5 average rating, 134 reviews

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.

Top Guest favourite
Bungalow in Lahaina
4.99 out of 5 average rating, 202 reviews

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

Guest favourite
Condo in Lahaina
4.89 out of 5 average rating, 137 reviews

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.

Guest favourite
Condo in Lahaina
4.95 out of 5 average rating, 104 reviews

3-min Walk to Beach, Modern & Fun Condo

- Walk across the street to beautiful, uncrowded Kahana Beach - Beach Bag, Beach Towels, Beach Chairs and Umbrella Included Free - See sea turtles and monk seals swimming in the ocean - 8 minute drive to Ka'anapali and Kapalua golf courses - Arcade machine with classic 80's games - Drop down bar on the lanai - A/C in the bedroom and living room - King size bed and queen sleeper sofa - Cable TV and smart TV, WiFi stereo - Walk to nearby groceries, restaurants, and bars - Fast WiFi

Top Guest favourite
Condo in Lahaina
4.99 out of 5 average rating, 144 reviews

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.

Top Guest favourite
Condo in Lahaina
4.99 out of 5 average rating, 159 reviews

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.

Top Guest favourite
Condo in Lahaina
4.98 out of 5 average rating, 195 reviews

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.

Top Guest favourite
Condo in Lahaina
4.99 out of 5 average rating, 134 reviews

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

Top Guest favourite
Holiday home in Lahaina
4.98 out of 5 average rating, 108 reviews

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

Quick stats about holiday rentals with a pool in Kaanapali

  • Total rentals

    4K properties

  • Total number of reviews

    41K reviews

  • Family-friendly rentals

    1.9K properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    2.6K properties have a dedicated workspace

  • Wi-Fi availability

    4K properties include access to Wi-Fi

Destinations to explore

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  2. United States
  3. Hawaii
  4. Maui County
  5. Kaanapali
  6. Rentals with pools