
Vacation rentals with a pool in Kaanapali
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Kaanapali

Total vacation rentals
Explore 4,760 vacation rentals in Kaanapali

Nightly prices starting at
Kaanapali vacation rentals start at G$2,089 GYD per night before taxes and fees

Verified guest reviews
Over 45,040 verified reviews to help you choose

Family-friendly vacation rentals
2,460 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
3,070 properties have a dedicated workspace

Wi-Fi availability
4,740 of Kaanapali vacation rentals include wi-fi 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!
Top-rated rentals with a pool in Kaanapali
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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 & located next to The Resort at Kapalua Bay (formerly Montage). 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, spas, & several bays/beaches for snorkeling, surfing, & relaxing, this is the perfect home base.
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Amazing Kapalua ,Stay 7 nights, only pay for 6 !
Our place is close to 3 beautiful beaches, 2 spectacular golf courses, tennis garden, hiking trails, whales, zip line, shops, restaurants, pools, barbecue, and spas. You’ll love our place because of the incredible views from the outdoor garden. It is huge and we call it our living room on the lawn. You'll love the ambiance, neighborhood, people. You will love everything about the Ridge at Kapalua. Our place is good for couples, solo adventurers, business travelers, not suitable for children.
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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.
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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.
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Maui Full Oceanfront Paradise
Indulge in the ultimate Maui getaway at our full oceanfront condo. The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants. For those warm tropical nights, rest easy knowing that the condo is equipped with air conditioning to ensure a comfortable night's sleep. The fully stocked kitchen provides all the essentials for cooking up a delightful island feast.
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Ka'anapali Oceanfront Dream-view Retreat with AC!
This serene oceanfront retreat is located along the Kaanapali coast, less than 50' from the crashing waves. The unit offers a whole lot of Aloha, with unobstructed views of an expansive crystal blue/green ocean, 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.
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Napili Bay Oceanview Resort Hideaway
Welcome to Napili Bay, Maui's hidden gem, and a favorite spot for some of the best snorkeling on Maui. Relax in the ocean breeze from your private lanai. Enjoy ocean views throughout the condo. Lush tropical landscaping, plumerias, monkeypods, and many more plant varieties throughout the property. 2nd floor studio condo, beautiful vaulted ceilings, low density property, old school Hawaiian resort. Easy access to world-class beaches, restaurants, shopping and golfing.
LocationFamilyHiking

❤️Best Views on Maui! Perfect for Honeymooners!!❤️
*** NO RESORT FEES! *** Newly renovated 10th-floor OCEANFRONT studio condo with the best views on Maui! All new furniture from Restoration Hardware! Drift to sleep on the new KING-sized memory foam mattress and awaken to the sounds of crashing waves. Enjoy breakfast looking for whales (from December through April), turtles and dolphins. The Mahana on Kaanapali Beach offers a prime location near shops, restaurants, food truck park, and the best beach!
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Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba
A legal short term rental! 1 bedroom, 1 bath with open floor plan. This condominium has a comfortable Cal-King bed in the bedroom and sofa sleeper in the living-room. **Central A/C*Fully equipped kitchen w/ granite counters*refrigerator*stove top + oven*coffee maker* microwave* dishwasher* washer/dryer* Free in room WiFi** Onsite gym is managed by an outside contractor and charges $9/day for useage.
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Rustic Upcountry retreat with breathtaking views!
Maui County Permits BBMP2019/0006 & SUP2 2019/0003 This is a BnB not a STRH Owners live on property At this time we are hosting to guests 12 or older. This property is terraced so not optimal for young children. This is a non smoking property. No smoking is allowed. Use of the pool, hot tub and dry sauna are private when reserved with our private calendar. Mahalo!
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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
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Kaanapali Fairway Villa 3BR/3BA.
Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.
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Popular amenities for Kaanapali rentals with a pool
House rentals with a pool

Maui direct ocean front . Super private
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Beautifully Remodeled 3 Bedrooms/2Bathrooms
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Kula Jewel - Pool, Hot Tub & Awesome Views!
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Oceanfront Paradise with Pickleball gear!
LocationFamilyTV

Stunning ocean view Villa, Heated pool, Wailea
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Studio Kaanapali Beach, Sleeps 3, Beach Cabana, Ja
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Oceanview Townhome • Modern • 2 Min Walk to Beach!
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3B2B w/HotTub FamilyComfort HawaiianaCharm Central
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Condo rentals with a pool

Rare 2 King Suites•Oceanfront•Watch Whales&Turtles
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Kaanapali Fairway Vista - Legal STR Hotel Zoned
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Beautiful Papakea 1 Bedroom with A/C
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MAHANA 505 OCEAN FRONT W/ SPECTACULAR VIEWS
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Oceanview Maui Condo, Turtles, Whales, Rainbows
LocationFamilyBeach

Romantic, Luxury Retreat w/Ocean View-Couples Only
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Mahana 1015 - Luxury Oceanfront Condo (1bd/2ba)
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Oceanfront Resort, Peaceful Mountain View Studio
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Other vacation rentals with a pool

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack
LocationFamilyGetting around

Best Papakea Oceanfront *No resort fees* Unit A106
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Spectacular views, prime location Kapalua, Maui.
LocationValueWifi

Mahana at Kaanapali- Beachfront Walkout Jewel
LocationFamilyWalkability

Ocean View steps from beach, dining, shopping 723
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Maui Sunset Vista Ocean View Condo in Kaanapali
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Romantic Oceanfront Escape | Panoramic Views
LocationParksQuiet

2BR/2BA | @ Alii Beachfront Resort | Sleeps 8
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When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$106,548 GYD | G$104,041 GYD | G$105,921 GYD | G$106,548 GYD | G$102,369 GYD | G$104,250 GYD | G$110,517 GYD | G$109,681 GYD | G$83,567 GYD | G$81,269 GYD | G$84,403 GYD | G$100,907 GYD |
| 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 |
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- Maui
- Kaanapali Beach
- Lahaina Beach
- Whalers Village
- Polo Beach
- Wailea Beach
- Maui Vista Condominium
- Kapalua Bay Beach
- Honolua Bay
- Big Beach
- Kepuhi Beach
- Haleakala National Park
- Black Rock Beach
- Black Sand Beach
- Old Lahaina Luau
- Ka'anapali Golf Courses
- Kihei Kai Nani
- KOA Resort
- Kamaole Beach Park II
- Maui Arts & Cultural Center
- Maui Ocean Center
- Aston Mahana at Kaanapali
- PacWhale Eco-Adventures
- Hāmoa Beach





