
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.

Oceanfront Condo at Napili Bay | Newly Refreshed
Thank you for checking out my newly refreshed OCEANFRONT condo located at the charming Napili Shores resort! ✨ FRESH LOOK, NEW COMFORT ✨ We’ve just given the entire condo a complete update! Enjoy brand-new modern furniture, freshly painted walls, and thoughtfully upgraded fixtures throughout. The entire home feels clean, bright, and beautifully refreshed—offering you an elevated, relaxing space for your ultimate Maui retreat.

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.

Gorgeous 2bed/2bath Papakea Oceanview!
Our spacious, remodeled two bedroom/two bathroom condo on the 4th floor is fully air conditioned with separate AC controls in each room. With its vaulted ceilings and a gorgeous ocean view from a roomy lanai, this is the perfect home base for up to 6 people to relax and enjoy all that Maui has to offer. Everything you need to enjoy your vacation is provided.

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

Private S. Maui home w/ocean views, pool, hot tub

Oceanfront Paradise with Pickleball gear!

Kula Jewel - Pool, Hot Tub & Awesome Views!

Exceptional Upcountry Villa, breathtaking views!

Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr

Stunning ocean view Villa, Heated pool, Wailea
Condo rentals with a pool

Kaanapali Fairway Vista - Legal STR Hotel Zoned

Aloha Kaanapali-Maui Eldorado Resort -J212

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

Oceanview Maui Condo, Turtles, Whales, Rainbows

Kaanapali Shores Modern Beachside Resort Condo

Maui Penthouse Studio Mahana 1213

MAHANA 505 OCEAN FRONT W/ SPECTACULAR VIEWS

Kaanapali Shores Double Oceanview Resort Living
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

Romantic Oceanfront Escape | Panoramic Views

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

Oceanfront Papakea Condo | Pools & Ocean Views

Stunning Oceanfront Penthouse

Premier Oceanfront Retreat in Lahaina
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $708 CAD | $691 CAD | $703 CAD | $708 CAD | $680 CAD | $692 CAD | $734 CAD | $728 CAD | $555 CAD | $540 CAD | $561 CAD | $670 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
- Wailea Beach
- Maui Vista Condominium
- Polo Beach
- Honolua Bay
- Kapalua Bay Beach
- Big Beach
- Kepuhi Beach
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- Black Sand Beach
- Haleakala National Park
- Old Lahaina Luau
- Ka'anapali Golf Courses
- Kihei Kai Nani
- KOA Resort
- Kamaole Beach Park II
- Aston Mahana at Kaanapali
- Maui Arts & Cultural Center
- Maui Ocean Center
- PacWhale Eco-Adventures
- Hāmoa Beach





