
Holiday rentals with a pool in Kaanapali
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Top-rated rentals with a pool in Kaanapali
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Luxury Mahana Studio-Great Views-WiFi-Free Park
Locally Owned and Operated Studio 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. Located on North Kaanapali Beach. Enjoy stunning views and the warm Maui sun inside while central AC keeps you cool and comfortable any time of day.

Eldorado Beach Resort Ka’anapali - Whalers Village
Eldorado resort charges a one time $65 plus $22 per day resort fee at check in. Maui Eldorado resort # K110 is a beautiful remodeled studio suite with a privacy wall that sleeps 4 comfortably. K110 has a fully equipped kitchen, AC, new washer & dryer and remodeled bathroom suite. Eldorado's beach cabana provides everything needed for an amazing day at the beach and fronts the nicest stretch of beach in all of Ka'anapali. Whalers Village restaurants, shops and activities are a 5 minute walk,

Peaceful Maui Bungalow | Ka Hale Aloha-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 @thoughtfulstays

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.

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.

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.

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.

Stunning ocean view, heated pool at home by Wailea
Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

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.

Charming Kaanapali cottage with ocean view
A charming "Old Hawaii" bungalow on lush landscaped tropical grounds, only a ten minute walk from Kaanapali Beach, the best beach in West Maui. Close to numerous restaurants and shops in the Kaanapali area. But so beguiling is the view of Lanai and Molokai islands as you drink your morning coffee, so inspiring the sunsets as you sip your cocktail in the late afternoon--you may never leave the lanai!

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!

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
Popular amenities for Kaanapali rentals with a pool
House rentals with a pool

Relaxation in Kapalua-Specials!

Mahalo Pono @ Ka'anapali Royal

Luxurious and Spacious 2BD Kaanapali Condo

Newly Remodeled Cottage

Go for an Ocean Swim From a Fun Beach Villa

Gram’s Maui Golf Cottage

Kula Jewel - Pool, Hot Tub & Awesome Views!

Studio Kaanapali Beach, Sleeps 3, Beach Cabana, Ja
Condo rentals with a pool

MAHANA 505 OCEAN FRONT W/ SPECTACULAR VIEWS

Turtles & Tales: Luxe Beachfront w/AC & Ocean view

Soothing Waves with 180° View In Kahana, HI

Condo in Lahaina, New Remodel, Amazingly Peaceful

Newly Relisted! Discounted rates. No resort fees

Oceanfront Resort, Peaceful Mountain View Studio

Beachfront on Kaanapali The Mahana 1106!

Stunning Luxury Remodel I Wailea Beach Villas J206
Other holiday rentals with a pool

Papakea Oceanfront A202

Mahana 1215 Penthouse

Premier Oceanfront Retreat in Lahaina

Incredible Fully Renovated -Top Floor Villa - D303

Maui Full Oceanfront Paradise

Oceanview Condo - Pools, Hot Tub, Spa & Beach

Ocean View Condo with Beachfront Cabana for Guests

Exceptional Oceanviews
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $581 AUD | $603 AUD | $639 AUD | $637 AUD | $566 AUD | $733 AUD | $748 AUD | $743 AUD | $566 AUD | $550 AUD | $572 AUD | $683 AUD |
| 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 |
Quick stats about holiday rentals with a pool in Kaanapali

Total holiday rentals
Explore 4,510 holiday rentals in Kaanapali

Nightly prices starting at
Kaanapali holiday rentals start at $14 AUD per night before taxes and fees

Verified guest reviews
Over 44,920 verified reviews to help you choose

Family-friendly holiday rentals
2,290 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
2,960 properties have a dedicated workspace

Wi-Fi availability
4,500 of Kaanapali holiday 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!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Kepuhi Beach
- Honolua Bay
- Polo Beach
- Kapalua Bay Beach
- Wailea Beach
- Ka'anapali Golf Courses
- Maui Ocean Center
- Hāmoa Beach
- Ulua Beach
- Black Rock Beach
- Old Lahaina Luau
- Big Beach
- Maui Vista Condominium
- Whalers Village
- Black Sand Beach
- Haleakala National Park
- Peahi
- Maui Sunset
- Kihei Kai Nani
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