
Vacation rentals with a pool in Kaanapali
Find and book unique homes with a pool on Airbnb
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!

MKV Resort - Last Minute Cancellation Sweet Deal
Note.. MKV charges $35 per day resort fee due at check in. Beautifully updated spacious studio with an ocean view. Amazing sunsets and whale watching are found here. Features new modern furniture, fresh paint and new decor throughout. MKV has direct beach access, two swimming pools, hot tubs, spa, gym, shuffleboard, outdoor BBQ's and Castaway's ocean front bar & grill. Parking is super convenient & free. Free trolly rides to Whalers village and Ka'anapali restaurants, markets and golf courses.

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,

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 & centrally located next to the Montage Resort. 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, shopping, spas, & several bays/beaches great for snorkeling, surfing, & relaxing, this is the perfect home base.

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.

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.

TOP FLOOR!!!! Oceanfront, free Wi-Fi, free parking
Honokowai area. Fresh & clean island vibe on the top floor, one unit away from the end. Practically hanging over the water's edge. Beautiful views of Molokai out the screened front door, as well as Lanai off the lanai. Striking floor-ceiling mirrors capture ocean views from virtually anywhere inside. Location in building catches wonderful trade winds. Listen to the sounds of the waves, just steps away & enjoy the endless sea turtle traffic right under your nose.

Perfect Romantic Getaway - Right on the Ocean!
You can't beat our little corner of paradise. This is truly our HAPPY PLACE! Relax on the lanai with your favorite beverage, and allow yourself to be serenaded by the crashing of waves and the refreshing salt water breeze. Our expansive ocean view is amazing every day and even better during prime whale watching season, which falls during the winter months. Stay put and enjoy or go out & explore the island of Maui.

Luxury Condo Near Whalers Village
Luxury + location at an unbeatable rate. Located in the heart of Ka'anapali on the golf course behind Whalers Village. Enjoy a 10-minute walk to world-famous Ka'anapali beach or relax at the resort’s pool and BBQ area. This spacious 1,800 sqft suite features 2 bedrooms, central A/C, and elegant travertine floors. (Please note: $160 parking fee is not included in the Airbnb rate and must be paid at check-in.)

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.

Direct Waterfront, Air conditioned, Amazing Views!
Stunning views! There is nothing better than sitting on your Lanai and listening to the waves! It is not unusual to spot whales and sea turtles while sitting on our Lanai. One of the nicest, if not THE nicest units at Papakea. Truly deluxe! Ocean front with full ocean view, just 30 feet from the ocean. If you are looking for multiple units, we are also owners of G104.
Popular amenities for Kaanapali rentals with a pool
House rentals with a pool

Mahalo Pono @ Ka'anapali Royal

Oceanfront Paradise with Pickleball gear!

Luxurious and Spacious 2BD Kaanapali Condo

Newly Remodeled Cottage

Go for an Ocean Swim From a Fun Beach Villa

Luxe 3BR Pualei Beach House Retreat

Stunning ocean view, heated pool at home by Wailea

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

Ocean View steps from beach, dining, shopping 961

Nohonani Resort #100

Absolutely Oceanfront - Corner Unit- Amazing Views

Beachfront Designer Remodel/AC, 180⁰ Ocean View

Stunning Sunset from A103's direct ocean view!

Ocean's Edge Romance: Sunsets, Whales, Views!

Beachfront on Kaanapali The Mahana 1106!

Honua Kai, K240 - House of the Quiet Shade
Other vacation rentals with a pool

Mahana 1215 Penthouse

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

Ma'alaea Surf Oceanfront 2 Bedroom Condo on 2nd Fr

Kaanapali Beach Club "Scenic View"

Garden Studio Steps to Beach King Bed & Extras

Top Floor OCEAN VIEWS - Resort

Best Papakea Oceanfront *No resort fees* Unit A106

Westin Nanea Hawaiian 2-BdrmVilla October 24-31st
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$86,018 GYD | G$89,157 GYD | G$94,598 GYD | G$94,180 GYD | G$83,715 GYD | G$108,411 GYD | G$110,714 GYD | G$109,876 GYD | G$83,715 GYD | G$81,413 GYD | G$84,553 GYD | G$101,086 GYD |
| 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 4,230 vacation rentals in Kaanapali

Nightly prices starting at
Kaanapali vacation rentals start at G$2,093 GYD per night before taxes and fees

Verified guest reviews
Over 42,900 verified reviews to help you choose

Family-friendly vacation rentals
2,090 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
2,770 properties have a dedicated workspace

Wi-Fi availability
4,220 of Kaanapali vacation 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
- Maui Ocean Center
- Ka'anapali Golf Courses
- Hāmoa Beach
- Black Rock Beach
- Old Lahaina Luau
- Ulua Beach
- Big Beach
- Maui Vista Condominium
- Whalers Village
- Haleakala National Park
- Peahi
- Black Sand Beach
- Maui Sunset
- Maui Arts & Cultural Center
- Kihei Kai Nani




