
Holiday rentals with a pool in Kaanapali
Find and book unique homes with a pool on Airbnb
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 $13 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

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

Wifi availability
4,500 of Kaanapali holiday 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.

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 beautifully remodeled studio suite with a privacy wall that sleeps 3 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. Amazing Whalers Village restaurants & shops are an easy 5 minute walk.

Whales Watch: Luxe Beachfront-180° Ocean views/AC!
Watch Whales breach during migration & sea turtles and sail boats sailing by while snuggled up in your dreamy, oceanfront kingsize bed with luxurious 600 count cotton sheets! If you love swimming with the turtles and the sound of the ocean, then this is the place for you. Luxuriously remodeled, very secluded corner unit, your Maui hideaway is just 15 feet from the ocean with unbeatable, 180 degrees ocean views. Located on the 5th floor of Valley Isle Resort in Kahana (Within the Hotel Zone).

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!! 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, steps to the ocean & walking distance to 2 beaches. Ka Hale Aloha will make you feel like you’re truly living the island life. * Check us out on IG at @thoughtfulstays

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, 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.

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.

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.

Luxury condo • 180° Ocean Views • Steps to Beach
Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

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

Mahalo Pono @ Ka'anapali Royal

Newly Remodeled Cottage

Go for an Ocean Swim From a Fun Beach Villa

Luxe 3BR Pualei Beach House Retreat

Ocean-View Large 2 Bedroom Townhouse in Kapalua

Kula Jewel - Pool, Hot Tub & Awesome Views!

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

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

Kapalua, luxe, ocean view, beach, spa, golf/tennis

Stunning Panoramic Oceanfront 2 Bed Bath with AC

Your Oasis by the Sea, stay at B103!

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

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Boathouse Studio Condo in Wailea

GORGEOUS Newly Remodeled Kaanapali Condo AVAIL !!!

Kaanapali Shores Modern Beachside Resort Condo
Other holiday rentals with a pool

Direct Oceanfront Mahana 2 King Bed Master Suites

Mahana 1215 Penthouse

OCEAN VIEW Kaanapali Cottage ICC 24

Mahana1002 Updated OceanFront Studio Stunning View

Incredible Fully Renovated -Top Floor Villa - D303

Maui Full Oceanfront Paradise

Ocean View Getaway~Beach, Pool, BBQ, Private Lanai

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $652 SGD | $636 SGD | $648 SGD | $575 SGD | $511 SGD | $662 SGD | $676 SGD | $671 SGD | $511 SGD | $497 SGD | $516 SGD | $617 SGD |
| 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
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Wailea Beach
- Kepuhi Beach
- Kapalua Bay Beach
- Polo Beach
- Old Lahaina Luau
- Whalers Village
- Black Rock Beach
- Maui Ocean Center
- Big Beach
- Maui Vista Condominium
- Hāmoa Beach
- Black Sand Beach
- Kihei Kai Nani
- Maui Arts & Cultural Center
- Haleakala National Park
- KOA Resort
- PacWhale Eco-Adventures
- Aston Mahana at Kaanapali
- Nakalele Blowhole





