
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.

180* Oceanfront View w/ AC! Remodel+2Pools+Clean
We are a LEGAL Short Term Rental. If STRs are banned, we will refund your reservation money. We are 6 miles north of the fire. Our beaches, sunsets & ocean are still amazing. Remodeled Large Studio w/ AC. Sleep 30' from the ocean to the sound of waves! PANORAMIC VIEWS/SUNSETS! 2 Relaxing Oceanside POOLS & hot tub. Fully-equipped kitchen. Walk-in rain shower. GREAT LOCATION! Close to Kaanapali, Kapalua, groceries, restaurants, beaches. TURTLES love this area. Free Parking. No Resort Fees.

3 Min to Beach, King Bed and Beach Gear
- Walk across the street to beautiful, uncrowded Kahana Beach - Beach chairs, cooler and umbrella included - See sea turtles, breaching whales swimming in the ocean - Close to Ka'anapali and Kapalua golf courses - A/C in bedroom and living room - King size bed and queen sleeper - Smart Cable TV, stereo - Walk to groceries, restaurants, and bars - Fast WiFi - Fully renovated condo with great mix of locals and vacationers - Popular restaurants Miso Phat, Captain Jacks and Dolly's are 1 minute away

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.

MKV Beach Resort Ka'anapali - Ocean & Sunset Views
Note... MKV resort charges $35 per day due at check in. Beautifully updated spacious studio with 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.

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.

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. This is a legally permitted vacation rental and is hotel zoned according to the County of Maui ordinances.

Private Napili Nest Near Beach
Tucked away, yet within minutes of Napili Bay, Kapalua resorts, golf, hiking and restaurants, Napili Nest is a private, remodeled and well-appointed end-unit studio with an A/C, balcony, peek-a-boo ocean/garden view and thoughtful guest amenities. Located in a quiet, low-density complex, this place is ideal for up to two guests seeking a peaceful getaway, living among locals. Busy nightlife fans would be happier in other parts of Maui.

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.

Sunsets and Turtles and Whales, Oh My!
Spectacular ocean views Whales and turtles galore(whale season Nov-March) Great snorkeling Gorgeous landscaping Pool, grills, shuffleboard, laundry, and huge sundeck Pristine beaches, grocery stores and world class shopping nearby Sleek and modern Maui hale Chef's kitchen Stainless steel appliances Tv & wifi Cali King bed with luxury linens Beach toys Cooling trade winds Boutique building Elevator and luggage carts Free parking

Amazing Ocean Views from 8th Floor! No Resort Fees
** NO RESORT FEES ** The Mahana on Kaanapali Beach is a beachfront resort that offers a prime location, close to many great shops and restaurants. Enjoy the peacefulness and privacy of this tropical resort. Unit 802 is high above the palm trees, for an unobstructed Ocean view overlooking neighboring islands of Molokai and Lanai. Perfect for whale watching or relaxing on the daybed on the lanai.

Direct Ocean front studio w ocean is ur back yard!
This is a hotel-zoned condo. It will not be affected by potential upcoming county regulations. Book with confidence!! Thank you for considering my direct ocean front studio condo in Kahana, my condo is located minutes outside of Lahaina , Kaanapali , Napili and Kapalua. You'll find the ocean view from my lanai/ room to be breathtaking and serene. This is truly an hidden gem on Maui.
Popular amenities for Kaanapali rentals with a pool
House rentals with a pool

Mahalo Pono @ Ka 'anapali Royal

Luxurious and Spacious 2BD Kaanapali Condo

Stunning One Bd Partial ocean, AC, wifi,Pool C209

Oceanfront Studio w/ Beach Access and Pool!

Maalaea Kai 307 - Maui Prime Oceanfront

International Colony Club 13 Cottage near Beach

Ridge 622- Wake Up to Sweeping Ocean Views in Maui

Stunning ocean view, heated pool at home by Wailea
Apartment rentals with a pool

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

Ocean Views- Beachfront- Steps to a Sandy Beach!

Napili Nani cottage for 2 w/AC ~ *Renovated*

Top floor updated oceanfront condo, AC, near shops

Makani Sands #203 1brm Beachfront condo

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

Oceanfront Napili Getaway | Serene 1br w/Lanai +AC

Spectacular Ocean Views, 1st Class, Luxury Condo
Other holiday rentals with a pool

Papakea Oceanfront A202

Mahana 1215 Penthouse

Ocean & Beach Front Condo w/Central Air (1BD/1BA)

Oceanfront King Bed Renovated Maui Kai Condo MK806

Maui El Dorado Kaanapali Beach Studio - G204

Kaanapali Shores Resort Studio #334 ~ West Maui ~

NEW Ocean Front Condo w Amazing Views

Best Papakea Oceanfront *No resort fees* Unit A106
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $523 SGD | $542 SGD | $575 SGD | $573 SGD | $509 SGD | $659 SGD | $673 SGD | $668 SGD | $509 SGD | $414 SGD | $435 SGD | $516 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 |
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 $13 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

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

Wifi availability
4,220 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!
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
- Princeville Holiday rentals
- Hilo Holiday rentals
- Napili-Honokowai Holiday rentals
- Serviced apartment rentals Kaanapali
- Beachfront rentals Kaanapali
- Rentals with an EV charger Kaanapali
- Pet-friendly rentals Kaanapali
- Rentals with an accessible-height bed Kaanapali
- Rentals with a patio Kaanapali
- House rentals Kaanapali
- Beach house rentals Kaanapali
- Apartment rentals Kaanapali
- Rentals with a washing machine and dryer Kaanapali
- Villa rentals Kaanapali
- Cottage rentals Kaanapali
- Waterfront rentals Kaanapali
- Rentals with a sauna Kaanapali
- Luxury rentals Kaanapali
- Hotel rooms Kaanapali
- Family-friendly rentals Kaanapali
- Rentals with a hot tub Kaanapali
- Beach apartment rentals Kaanapali
- Fitness-friendly rentals Kaanapali
- Rentals with a kayak Kaanapali
- Flat rentals Kaanapali
- Holiday home rentals Kaanapali
- Rentals with a firepit Kaanapali
- Resort rentals Kaanapali
- Rentals with outdoor seating Kaanapali
- Rentals with beach access Kaanapali
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Kepuhi Beach
- Honolua Bay
- Kapalua Bay Beach
- Wailea Beach
- Maui Ocean Center
- Polo Beach
- Hāmoa Beach
- Ka'anapali Golf Courses
- Old Lahaina Luau
- Big Beach
- Whalers Village
- Ulua Beach
- Maui Arts & Cultural Center
- Peahi
- Haleakala National Park
- Maui Vista Condominium
- Kihei Kai Nani
- Black Rock Beach
- Maui Sunset
- Kahana Beach




