
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 $14 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

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

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

Mahana at Kaanapali- Beachfront Walkout Jewel
Maui Gov’t Approved Short Term Rental - Hotel District- Direct beach access with ground floor spacious lanai. Unreal views from this one bedroom, one sofa bed ground level entry, beachfront condo located directly on Kaanapali Beach. Central AC with LR and BR providing separate direct walkout to the lanai and 15 steps away is the beach! 75" TV, Sonos system, Apple TV, washer/dryer etc. Stocked kitchen includes coffee makers and supplies to get yourself ready for romantic dinners with the sunset!

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.

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.

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.

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.

Kaanapali Fairway Vista - Legal STR Hotel Zoned
Escape to a Slice of Paradise – Where the Fairway Meets the Ocean. This beautifully appointed condo offers the best of Kaanapali living, featuring a prime golf course front position with serene, sweeping views and a sparkling partial ocean view that will take your breath away. Wake up to the sight of golfers setting off on the world-renowned Kaanapali Golf Courses. In the afternoon, relax on your private lanai and watch the sunset paint the Pacific Ocean in hues of gold and orange.

Beachfront Resort, Peaceful Mountain View Studio
Come stay at Lahaina Shores 506: - Oceanfront Building: Direct access to a sandy beach, pool, and hot tub just steps from the lobby - Mountain Views: Wake up to stunning sunrises from your 5th-floor lanai - Sunny & Clear: West Maui averages ~290 sunny days/year! - Amenities Nearby: Minutes drive to open spots like the Cannery Mall, Lahaina Gateway Center, & classic restaurants - West Maui: Only ~35 mins from the airport Note: Car recommended to explore the island

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.

Fresh Reno on 8th Floor Studio - Amazing Views
** NO RESORT FEES ** Just finished renovation on this 8th floor STUDIO at The Mahana! New furniture, cabinets, flooring, appliances, and housewares. Be the first guests to enjoy the luxury! The Mahana on Kaanapali Beach is a beachfront resort that offers a prime location, close to many great shops and restaurants. Enjoy the peacefulness and privacy of this tropical resort.

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

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.

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

Maui direct ocean front . Super private

Beautifully Remodeled 3 Bedrooms/2Bathrooms

Kula Jewel - Pool, Hot Tub & Awesome Views!

Exceptional Upcountry Villa, breathtaking views!

Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr

Go for an Ocean Swim From a Fun Beach Villa

Stunning ocean view Villa, Heated pool, Wailea

Maui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool
Condo rentals with a pool

Oceanview Maui Condo, Turtles, Whales, Rainbows

Aloha Kaanapali-Maui Eldorado Resort -J212

Kaanapali Shores Double Oceanview Resort Living

Ocean Views- Beachfront- Steps to a Sandy Beach!

Kaanapali Shores Modern Beachside Resort Condo

MAHANA 505 OCEAN FRONT W/ SPECTACULAR VIEWS

Maui Penthouse Studio Mahana 1213

Oceanfront Two Bedroom at Kaanapali Shores #504
Other vacation rentals with a pool

Direct Beachfront 1BD Escape w AC - MKV 179

Beachfront on Kaanapali The Mahana 1106!

Ocean View steps from beach, dining, shopping 723

Oceanfront Papakea Condo | Pools & Ocean Views

2BR/2BA | @ Alii Beachfront Resort | Sleeps 8

Romantic Oceanfront Escape | Panoramic Views

1 Bedroom Corner Oceanfront #701

Ocean View Condo with Beachfront Cabana for Guests
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $706 CAD | $690 CAD | $702 CAD | $706 CAD | $679 CAD | $691 CAD | $733 CAD | $727 CAD | $554 CAD | $539 CAD | $560 CAD | $669 CAD |
| 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
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- Maui Arts & Cultural Center
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