
Holiday 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.

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

Ka'anapali Oceanfront 1BR w/ Dream-views & AC!
This serene beachfront retreat is located along the Kaanapali coast, less than 50' from the beach and 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.

Eldorado Last Minute Cancellation - Discount Deal!
* 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.

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.

WOW! What a view! Ka’anapali condo w/AC, King Bed!
Enjoy the relaxing, peaceful Maui vacation you have been dreaming of! Maui Kai #202 greets you with breathtaking ocean views as soon as you open the door! You’ll love being right on the ocean in this recently updated studio condo at Maui Kai. You're so close to the ocean, you'll feel like you're on a cruise (without the swaying of the ship!). Let your troubles melt away with each crashing wave… Note: This is a permitted vacation rental located in the “hotel zone”.

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

Stylish Love Hideaway, Maui Kaanapali Oceanfront
Oceanfront studio in one of a kind boutique condominium, on world famous Kaanapali Beach. Wake up to a breathtaking oceanview, take it all in from spacious lanai, fall asleep to the sound of the ocean every night Located on the 3rd floor with close touch to ocean breeze and fantastic views, easy access to world-class beaches, restaurants, shopping and golfing
Popular amenities for Kaanapali rentals with a pool
House rentals with a pool

Mahalo Pono @ Ka'anapali Royal

Oceanview • Family-friendly • Sleeps 8 • Parking

Luxurious and Spacious 2BD Kaanapali Condo

Newly Remodeled Cottage

Oceanfront Studio w/ Beach Access and Pool!

Oceanview Townhome • Modern • 2 Min Walk to Beach!

Stunning ocean view, heated pool at home by Wailea

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

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba

Your Oasis by the Sea, stay at B103!

Condo in Lahaina, New Remodel, Amazingly Peaceful

Luxury condo • 180° Ocean Views • Steps to Beach

Maui El Dorado Kaanapali Beach Studio - G204

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

Private Napili Nest Near Beach

Best Location in Kapalua, walk to beach, spacious
Other holiday rentals with a pool

Maui Oceanfront-King Bd/Ba, AC & Epic Ocean Views!

Maui Resort Rentals: Honua Kai Hokulani 213

Mahana 1215 Penthouse

Oceanfront King Bed Renovated Maui Kai Condo MK806

Ocean, Sunsets, Whales & Turtles at Honuloha

Right on the water in West Maui. # 105

Beautiful, Remodeled Ocean View Condo

Beachfront on Kaanapali The Mahana 1106!
When is the best time to visit Kaanapali?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 346 | € 359 | € 381 | € 379 | € 337 | € 436 | € 446 | € 442 | € 337 | € 328 | € 340 | € 407 |
| 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 € 8 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!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Kepuhi Beach
- Honolua Bay
- Kapalua Bay Beach
- Wailea Beach
- Polo Beach
- Maui Ocean Center
- Hāmoa Beach
- Ka'anapali Golf Courses
- Old Lahaina Luau
- Ulua Beach
- Big Beach
- Black Rock Beach
- Whalers Village
- Maui Sunset
- Peahi
- Maui Vista Condominium
- Kihei Kai Nani
- Haleakala National Park
- Kahana Beach
- Maui Arts & Cultural Center




