Holiday rentals with a pool in Kaanapali

A spacious studio features large windows that offer panoramic ocean views. A cozy seating area with a sofa and table complements a queen-size bed adorned with turquoise accents. A television is mounted on the wall, while a sliding door provides access to a private lanai.

4.99 out of 5 average rating, 279 reviews

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.

The living area features a gray sofa with patterned cushions facing a wooden coffee table. A wall-mounted TV is positioned nearby, and large glass doors bring in natural light, opening to a private lanai with views of the outdoors. Decor is minimalistic and modern.

4.96 out of 5 average rating, 149 reviews

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

A dining setup is presented on a patio table with bowls and turquoise glasses. A decorative pineapple stands at the center. The background features a stunning ocean view with clear blue waters and a line of greenery, under a bright sky with soft clouds.

4.97 out of 5 average rating, 101 reviews

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!

A private lanai features a round dining table with four chairs, surrounded by lush palm trees and stunning ocean views. The table is set with dinnerware and a vase of tropical flowers, offering an inviting space for outdoor dining.

4.98 out of 5 average rating, 248 reviews

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.

A spacious living area is furnished with a seven-piece sectional sofa and a comfortable twin daybed. A coffee table rests on a patterned area rug. Floor-to-ceiling windows provide garden views, while a ceiling fan adds comfort to the inviting ambiance.

4.99 out of 5 average rating, 144 reviews

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.

The open-concept living space features a modern kitchen with sleek cabinetry and a bar top overlooking a sunlit living area. Floor-to-ceiling windows reveal panoramic ocean views and access to a comfortable seating area, inviting relaxation in a coastal setting.

4.99 out of 5 average rating, 141 reviews

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.

A tranquil pool area is surrounded by lush tropical vegetation, with a mix of vibrant flowers and palm trees. Relaxing lounge chairs are positioned near the water, offering scenic views of distant mountains and the ocean. The sky is clear, enhancing the inviting atmosphere.

4.87 out of 5 average rating, 190 reviews

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.

A spacious living area is furnished with a soft gray sofa adorned with decorative pillows, complemented by a wooden coffee table with glass top. A vibrant ocean view is framed by large windows, and a cozy dining set is positioned on the lanai, enhancing the inviting space.

4.96 out of 5 average rating, 114 reviews

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.

A small balcony is furnished with a wooden table and two chairs, adorned with a vase containing green leaves and a red flower. A rainbow is visible in the background, with lush greenery surrounding the space.

4.98 out of 5 average rating, 119 reviews

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.

An outdoor dining area is presented on a private lanai, featuring a table set with two glasses and plates of food. In the background, palm trees sway against a clear blue sky, overlooking stunning ocean views that include distant islands.

4.98 out of 5 average rating, 194 reviews

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

An outdoor lanai features a small table and two wicker chairs, offering a direct view of the expansive Pacific Ocean. The ocean's vibrant blue waters stretch toward the horizon under a partly cloudy sky, creating a serene and inviting area for relaxation.

4.99 out of 5 average rating, 205 reviews

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.

A spacious lanai offers a stunning ocean view, featuring a glass-top table with two wicker chairs. Bright blue beverages are placed on the table, while blue skies and gentle waves stretch out towards the horizon.

4.99 out of 5 average rating, 113 reviews

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living room features a sectional sofa and an accent chair with a vibrant pattern, complemented by a round coffee table. Large glass doors open to a water-view lanai, allowing natural light to fill the space. Contemporary art adds visual interest to the neutral walls.

4.98 out of 5 average rating, 41 reviews

Mahalo Pono @ Ka'anapali Royal

A vibrant view showcases lush greenery and a spacious pool area, framed by tall palm trees. Beyond the pool, the expansive golf course and distant ocean can be seen, set against a bright blue sky adorned with a few fluffy clouds.

5 out of 5 average rating, 5 reviews

Luxurious and Spacious 2BD Kaanapali Condo

A serene sandy beach is shown with gentle waves lapping against the shore. Sunbathers are positioned leisurely on the sand, and a few umbrellas provide shade nearby. Lush palm trees line the back of the beach, creating a tranquil atmosphere under a clear blue sky.

5 out of 5 average rating, 53 reviews

Newly Remodeled Cottage

4.97 out of 5 average rating, 37 reviews

A private balcony features a wooden table surrounded by four chairs, with a serene view of lush greenery and palm trees. Bright sky and the distant buildings of the resort can be seen, suggesting a peaceful outdoor setting.

Home in Kihei

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

Superhost

A balcony showcases direct oceanfront views, featuring two chairs and a glass table. Palm trees sway gently in the breeze, and the shimmering blue water extends to the horizon. The sky is bright with a few scattered clouds, enhancing the serene coastal ambiance.

4.83 out of 5 average rating, 6 reviews

Oceanfront Studio w/ Beach Access and Pool!

Superhost

A spacious outdoor seating area features a comfortable sectional sofa adorned with decorative pillows. A coffee table holds a tray with fruits and two champagne glasses, surrounded by lush tropical plants and palm trees, creating a serene outdoor retreat.

4.94 out of 5 average rating, 36 reviews

International Colony Club 20 Remodeled 2BD Pool AC

4.98 out of 5 average rating, 43 reviews

A relaxed living area features a blue sectional sofa with red and white decorative pillows. A coffee table sits in front, and a work desk is positioned near a glass sliding door that provides views of the ocean and surrounding palm trees.

Home in Wailuku

Maalaea Kai 307 - Maui Prime Oceanfront

4.94 out of 5 average rating, 18 reviews

Ridge 622- Wake Up to Sweeping Ocean Views in Maui

Apartment rentals with a pool

Ocean views are visible through expansive glass doors in a bright living area. Tropical plants add greenery, and comfortable seating options are arranged for relaxation. The sunlit space offers a seamless transition to the outdoor area, enhancing the beachside atmosphere.

4.95 out of 5 average rating, 140 reviews

Ocean Views- Beachfront- Steps to a Sandy Beach!

The kitchen area features a modern countertop with two white bar stools, each adorned with blue cushions. Cabinets line the walls, accompanied by a refrigerator and other appliances. Natural light fills the space, creating a bright and open atmosphere.

4.93 out of 5 average rating, 474 reviews

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

A serene lanai offers a round table with two cushioned chairs, positioned to overlook the ocean. A decorative shell rests on the table, while the expansive sea and distant mountains provide a tranquil backdrop, showcasing varying shades of blue and green in the water.

4.96 out of 5 average rating, 52 reviews

Top floor updated oceanfront condo, AC, near shops

A spacious living area showcases modern tropical design with large windows providing unobstructed views of the ocean and sunset. A comfortable brown sofa and armchairs create a cozy seating arrangement, complemented by a round coffee table and woven area rug. Decorative plants add a touch of nature.

5 out of 5 average rating, 48 reviews

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

A sparkling pool is framed by lush tropical landscaping and swaying palms. Comfortable lounge chairs with umbrellas provide shaded seating options nearby. The inviting water reflects a clear blue sky, creating a peaceful ambiance perfect for relaxation.

4.97 out of 5 average rating, 152 reviews

Tranquil Honokowai Condo•King Bed•Walk to Beaches

A dining table is positioned on a balcony, featuring a scenic ocean view. Two place settings are arranged with woven placemats and blue dishware. A bottle of wine and glasses are set at the center, while a palm tree is visible in the background against a clear blue sky.

4.94 out of 5 average rating, 204 reviews

OCEAN FRONT CONDO IN KAHANA NEAR NAPILI! ,KAPALUA

A modern living area is depicted, featuring a gray sectional sofa, a sleek coffee table, and a wall-mounted TV. Large sliding glass doors provide a view of the ocean, while the space is illuminated by natural light, enhancing the open, airy feel.

4.98 out of 5 average rating, 181 reviews

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

A warm sunset illuminates the sky over the ocean, viewed from a cozy lanai. A wooden table is set with two glasses and a bottle, accompanied by two chairs featuring soft cushions. Lush greenery can be seen in the distance, blending with the scenic backdrop.

4.98 out of 5 average rating, 120 reviews

Spectacular Ocean Views, 1st Class, Luxury Condo

Other holiday rentals with a pool

5 out of 5 average rating, 8 reviews

Maui Beach Frt Condo w/ AC Kaanapali Shores Resort

Superhost

Large windows provide unobstructed ocean views, allowing natural light to fill the living area. A comfortable blue sofa and a textured chair are positioned near a stylish side table. Neutral tones enhance the serene ambiance, inviting relaxation while enjoying the scenery.

5 out of 5 average rating, 4 reviews

Mahana 1215 Penthouse

A panoramic view of the ocean showcases varying shades of blue, with gentle waves lapping at the sandy shore. Palm trees sway in the breeze, and a community area with thatched umbrellas is visible in the foreground. The scene is framed by an adjacent building.

4.94 out of 5 average rating, 86 reviews

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

A private lanai balcony showcases a round table and two chairs, offering unobstructed ocean views. The tranquil water reflects soft sunlight, creating a serene atmosphere. The surrounding railing frames the picturesque setting, making it ideal for enjoying sunsets.

4.96 out of 5 average rating, 74 reviews

Oceanfront King Bed Renovated Maui Kai Condo MK806

4.98 out of 5 average rating, 442 reviews

A bright sleeping area features a spacious bed dressed in crisp white linens. Flanking the bed are two nightstands with lamps. A smart TV is mounted on the wall opposite, and large windows with white shutters allow natural light to enter the room.

Apartment in Wailea

Boathouse Studio Condo in Wailea

A studio bedroom features a wooden bed frame with a neatly made bed. Two bedside tables with lamps are positioned on either side. A decorative painting hangs above the bed, and a flat-screen TV is mounted on the wall opposite. Natural light fills the space through a nearby window.

5 out of 5 average rating, 42 reviews

Maui El Dorado Kaanapali Beach Studio- G204

5 out of 5 average rating, 13 reviews

Maui Resort Rentals: Honua Kai Hokulani 930