
Holiday 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!

Eldorado Beach Resort Ka’anapali - Whalers Village
* The Eldorado resort charges a one time $65 plus $22 per day resort fee at check in. Maui Eldorados beach resort Unit # K110 is a beautifully updated large studio suite with a privacy wall that sleeps 4 comfortably. Featuring a gorgeous fully equipped kitchen, tile floors, AC, new washer/ dryer and beautifully remodeled bathroom suite. The beach cabana with everything you need fronts the nicest stretch of beach in all of Ka'anapali. Whalers village is an easy 5 minute walk from the resort.

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.

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.

OCEAN FRONT Condo at Napili Bay, Near Kapalua!
Thank you for checking out my OCEAN FRONT condo located at the Charming Napili Shores resort. This recently renovated condo is in the high demand I building, which is the closest to the ocean in the complex. Imagine every morning you enjoy the brunch ordered from the famous Gazebo restaurant at your own Lanai right beside the ocean; Soak up the sunshine on the Napili beach steps away from the resort during the day, and come back in the evening to watch the stunning sunset in your room!

Oceanfront Maui Penthouse • Lanai • Pool • Views
Mar 28 to Apr 3rd OPEN!! 🌺 5-star Maui Oceanfront Penthouse | Corner Unit with Epic Views of the ocean and the mountains! 🐋 Experience breathtaking sunsets from this top-floor corner unit 2BR, 2BA condo 🌊 with panoramic views of the Pacific, Lanai, Molokai & West Maui Mountains 🏔️. Spot whales 🐋 and turtles 🐢 right from your lanai! Walk to beaches, restaurants, and shops. Soak up the sun, swimming in the pool or BBQ under the palm trees. ✅ Book now for the best rates!

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.

Kapalua, luxe, ocean view, beach, spa, golf/tennis
KAPALUA - Best location! Welcome to the luxuriously Kapalua Bay Villa #37B1. Bright and airy, with comfortable furniture and modern appliances. Scenic ocean view, a 5-minute walk to Kapalua Bay, Montage Resort, tennis, golf, hiking, zip-lining, amazing restaurants, and a first-class spa. Kapalua Bay Villas is a low-density community within the Kapalua Resort—a 15-minute drive to Kaanapali, and a 40-minute drive to Central Maui to explore the island.

Ready for some Sun? Winter blues got ya? Come on!
Winter Spec! Tastefully decorated one bedroom unit. All tile floors, Cal King bed! Hale Ono Loa #311 Flat screen TV, Cal King bed, HUGE lanai, onsite laundry facilities. All tile flooring! Tastefully remodeled! Swim in the large in ground pool and snorkel with turtles right in front of property! Fully equipped condo is supplied with all basic amenities including linens, cooking utensils and starter supplies of paper and cleaning products.

Beachfront Designer Remodel/AC, 180⁰ Ocean View
Watch the Whales breach during their migration and boats sailing by while sitting up in your dreamy oceanfront bedroom with a cup of coffee! If you love the sound of the ocean, then this is the place for you. Luxuriously remodeled Island Oasis, just 15 feet from the ocean with unbeatable, 180 degrees ocean views. Super private, secluded corner unit located on the 5th floor of Valley Isle Resort in Kahana. Inside the Hotel Zone.

Luxury Vacationing Modern Condo April Specials
JUST RENOVATED THIS BEAUTIFUL CONDO IS BORDERING KIHEI AND WAILEA. THE CONDO BOASTS 17 FT CEILINGS, 1025 sq ft, 4 FRENCH DOORS THAT OPEN OUT TO A DOUBLE BALCONY WITH INCREDIBLE VIEWS OF THE OCEAN AND VOLCANO. TENNIS COURTS, SWIMMING POOL, BOCCE BALL, SHUFFLE BOARD,PUTTING GREEN AND ACROSS THE STREET FROM KEAWAKAPU BEACH. PERFECT FOR A FAMILY VACATION. ***ALL HAWAII STATE TA GE TAXES ARE INCLUDED IN THESE PRICES **

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

Oceanview • Family-friendly • Sleeps 8 • w/Parking

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!

1 Kaanapali Beach C101 Maui Eldorado, Sleeps 3, Be

Maui direct ocean front . Super private
Condo rentals with a pool

MKV Beach Resort Ka'anapali - Ocean & Sunset Views

Oceanfront condo Maui Kai 602, Lahaina

Modern Maui Vista Condo across from Beach in Kihei

1 Bedroom Corner Oceanfront #701

Luxury 2 BD Condo at Honua Kai Resort on the Beach

Luxury condo • 180° Ocean Views • Steps to Beach

Oceanview Condo - Pools, Hot Tub, Spa & Beach

Beachfront on Kaanapali The Mahana 1106!
Other holiday rentals with a pool

Come and enjoy Ocean front luxury! C203

Oceanfront Relaxing Cozy Getaway-Royal Kahana 312-

Wailea Ekahi Gem |Walk to Beach |May Special!

Incredible Fully Renovated -Top Floor Villa - D303

Maui Full Oceanfront Paradise

Fresh to Market: Private End Oceanfront Sanctuary

Pent house on the ocean

Perfect Studio in paradise!
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $702 NZD | $728 NZD | $772 NZD | $769 NZD | $683 NZD | $885 NZD | $904 NZD | $897 NZD | $683 NZD | $665 NZD | $690 NZD | $825 NZD |
| 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 4,230 holiday rentals in Kaanapali

Nightly prices starting at
Kaanapali holiday rentals start at $17 NZD per night before taxes and fees

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

Family-friendly holiday rentals
2,090 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

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

Wi-Fi availability
4,220 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!
Destinations to explore
- Honolulu Holiday rentals
- Oahu Holiday rentals
- Kauai Holiday rentals
- Island of Hawai'i Holiday rentals
- Waikīkī Beach Holiday rentals
- Kailua-Kona Holiday rentals
- Kona Holiday rentals
- Kihei Holiday rentals
- North Kona Holiday rentals
- Hilo Holiday rentals
- Princeville Holiday rentals
- Napili-Honokowai Holiday rentals
- Beachfront rentals Kaanapali
- Rentals with a hot tub Kaanapali
- Pet-friendly rentals Kaanapali
- Rentals with a kayak Kaanapali
- Condo rentals Kaanapali
- Waterfront rentals Kaanapali
- Rentals with a patio Kaanapali
- Beach condo rentals Kaanapali
- Beach house rentals Kaanapali
- Villa rentals Kaanapali
- Rentals with a washing machine and dryer Kaanapali
- Serviced apartment rentals Kaanapali
- Hotel rooms Kaanapali
- Luxury rentals Kaanapali
- Apartment rentals Kaanapali
- Rentals with an accessible height bed Kaanapali
- Rentals with an EV charger Kaanapali
- Fitness-friendly rentals Kaanapali
- Rentals with outdoor seating Kaanapali
- House rentals Kaanapali
- Cottage rentals Kaanapali
- Rentals with beach access Kaanapali
- Family-friendly rentals Kaanapali
- Resort rentals Kaanapali
- Holiday home rentals Kaanapali
- Rentals with a sauna Kaanapali
- Rentals with a fire pit Kaanapali
- Rentals with breakfast Kaanapali
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Kapalua Bay Beach
- Polo Beach
- Wailea Beach
- Maui Ocean Center
- Hāmoa Beach
- Ka'anapali Golf Courses
- Ulua Beach
- Old Lahaina Luau
- Big Beach
- Whalers Village
- Black Rock Beach
- Haleakala National Park
- Peahi
- Maui Vista Condominium
- Maui Arts & Cultural Center
- Black Sand Beach
- Kihei Kai Nani
- Kahana Beach
- Maui Sunset




