
Vacation 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.

Ocean Views- Beachfront- Steps to a Sandy Beach!
Views! Views! Views! From the moment you enter Valley Isle unit 110 you will be mesmerized with ocean views from every room. This corner unit is located on the 1st floor and has direct access, steps to a sandy beach. Watch rainbows, turtles or whales from the spacious Lanai, a comfortable scenic space where you can spend your mornings, days or evenings, located within 15 feet from the ocean. Bedroom sliding door opens to tranquil sound of the ocean, doz-off with open doors to the sound of waves.

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!

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

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.

Ocean's Edge Romance: Sunsets, Whales, Views!
Bask as you wake to the sound of the waves crashing below and the sight of pristine turquoise water and expansive rainbows. You may pinch yourself as you take it all in, thinking you are still dreaming. We are excited to be able to offer Maui Kai 807, a studio condo in the original beach front high-rise on Maui's west side. No other resort in Kaanapli will put you closer to the ocean's edge. Enjoy the sights of sunsets, turtles, dolphins, and whales (Dec-March) right from your lanai.

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.

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.

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

Mahalo Pono @ Ka'anapali Royal

Kaanapali Royal G303 - Luxury & Spacious

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

Stunning ocean view, heated pool at home by Wailea

Kula Jewel - Pool, Hot Tub & Awesome Views!
Condo rentals with a pool

Amazing View!

Oceanfront Getaway, Brand New, Steps To Beach

Your Oasis by the Sea, stay at B103!

Mahana1002 Updated OceanFront Studio Stunning View

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

Soothing Waves with 180° View In Kahana, HI

GORGEOUS Newly Remodeled Kaanapali Condo AVAIL !!!

Oceanfront Resort, Peaceful Mountain View Studio
Other vacation rentals with a pool

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

Direct Oceanfront Mahana 2 King Bed Master Suites

Mahana 1215 Penthouse

OCEAN VIEW Kaanapali Cottage ICC 24

Incredible Fully Renovated -Top Floor Villa - D303

Maui Full Oceanfront Paradise

Beachfront on Kaanapali The Mahana 1106!

Ground Floor- New Renovation, AC & steps to Ocean
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $704 CAD | $687 CAD | $699 CAD | $621 CAD | $552 CAD | $715 CAD | $730 CAD | $724 CAD | $552 CAD | $537 CAD | $557 CAD | $666 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 |
Quick stats about vacation rentals with a pool in Kaanapali

Total vacation rentals
Explore 4,510 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 44,920 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

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

Wifi availability
4,500 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!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Wailea Beach
- Honolua Bay
- Kepuhi Beach
- Kapalua Bay Beach
- Polo Beach
- Old Lahaina Luau
- Black Rock Beach
- Whalers Village
- Big Beach
- Maui Vista Condominium
- Maui Ocean Center
- Kihei Kai Nani
- Black Sand Beach
- Hāmoa Beach
- Maui Arts & Cultural Center
- Haleakala National Park
- KOA Resort
- PacWhale Eco-Adventures
- Aston Mahana at Kaanapali
- Maui Tropical Plantation





