Vacation rentals with a pool in Moloka‘i

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Top-rated rentals with a pool in Moloka‘i

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

An oceanfront pool is surrounded by palm trees, creating a tropical setting. The pool features a curved shape with a shallow entry and steps leading into the water. Clear skies can be seen above, and the ocean is visible in the background.

Cottage in Molokai

4.95 out of 5 average rating, 101 reviews

Oceanfront 2-Bedroom Cottage, Stunning Views, Pool

Enjoy stunning sunset views of the Pacific Ocean, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, oceanfront cottage with a large covered lanai. This No Smoking two-Level cottage is located at the Kepuhi Beach Resort, close to pristine beaches, trails, and an oceanfront pool. The cottage is a peaceful place to work online, explore or just unplug and relax. You will experience colorful sunsets, breezes, tropical birds, beaches, and breaching whales in the winter.

Superhost

A refreshing pool is surrounded by lounge chairs, with palm trees swaying in the breeze. The clear blue water reflects the sky, creating a serene outdoor space. A nearby building adds to the relaxed atmosphere.

Apartment in Lahaina

4.86 out of 5 average rating, 224 reviews

Beautiful, Remodeled Ocean View Condo

Our beautiful studio (C307) offers all the luxuries of home. It has been remodeled including new stainless steel appliances, furniture and granite counters.New furnishings include: pillow top QN mattress/bedding, black out curtains and washer/dryer. A full furnished kitchen and lots of closet space make it very comfortable. There is also a new queen size 5" memory foam sleeper sofa. New shared gas grills, 3 tennis courts, two 12-hole putting greens, jet spas, 2 pools, and shuffleboard!

Top guest favorite

A clear swimming pool is surrounded by palm trees and tropical foliage, providing a serene view. In the background, a shaded gazebo adds to the landscape while the ocean can be seen beyond the pool, complementing the tranquil atmosphere.

Condo in Lahaina

4.97 out of 5 average rating, 114 reviews

60%OFF APRIL-JUNE/25! Ocean views! Air Conditioned

Thank you for checking us out! We have dropped our price 60% for the month of April 2025 to end of June 2025. They are doing re-piping to the building adjacent to us and there will be construction noise Monday to Friday 9:00am to 4:30pm. NO work to be done evenings, weekends or holidays. You must acknowledge this at time of booking. Most people are at the beach, pool or touring the island during the day so this might be an opportunity for you to stay in an amazing condo for a great price!!!

Superhost

A vibrant sunset is captured over the ocean, with warm oranges and cool blues blending in the sky. Silhouetted palm trees frame the scene, and the distant outline of land is visible across the water, enhancing the serene coastal atmosphere.

Condo in Lahaina

5 out of 5 average rating, 4 reviews

Resort Stay Entire 1Bdr Villa Kaanapali Beachfront

This resort has the most amazing pool on the island, Salt Water Based !! So easy on the skin ;) Olympic size pool about 2.5 Acres with Slide, waterfalls , plunge pool, volleyball. Snorkel Equipment rental , Beach chairs etc. All you need to have a great Hawaiian Vacation with The Family. Awesome Luau on Site every Teus Night! This price is for scenic if avail. Otherwise upgrade is additional if oceanview is what we have for your dates:) Mahalo For coming back to The West Side Best Side!

Superhost

Condo in Lahaina

4.89 out of 5 average rating, 113 reviews

Remodeled Kaanapali golf resort 1500ft condo w/AC

Amazing resort property, on Kanapalli golf course. Walk to Whaler's village. Golf cart service will come to your room and transport you Maui's only private beach cabana (exclusively for our complex only) offering PRIVATE RESTROOMS, kitchen and dining facilities, chairs and towel service. Other Amenities: • Central AC • Front desk w/Concierge • Washer/Dryer • Snorkel Gear, Boogie boards, sand toys • Gym • 3 pools • Wifi • Golf (extra) Rate excludes $70 check-in + $17/nt resort fee.

Guest favorite

An aerial view captures the complex's landscaped grounds, featuring a swimming pool surrounded by lounge chairs and tropical plants. Palm trees gently sway in the breeze, while neighboring buildings provide a glimpse of the comfortable accommodations available.

Condo in Lahaina

4.9 out of 5 average rating, 305 reviews

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.

Superhost

A clear swimming pool is surrounded by white lounge chairs placed on a sun-kissed patio. Lush green foliage provides privacy on one side, while a building is visible in the background under a bright blue sky with scattered clouds.

Condo in Lahaina

4.82 out of 5 average rating, 162 reviews

Whale Season Special! T-046-692-0448-02

We love to host! Listing was paused to help fire families! Read our 5*reviews! Directly across from a State Beach Park with morning sea turtles and the best Maui Sunsets. Food Trucks,Grocery store, Badass coffee, Miso Phat Sushi all in walking distance and give it a neighborhood feel. Onsite BBQ, Newly Updated Pool and Free Parking! 10 min to Kaanapali / Napili. Beach towels/Chairs provided. Clean, comfortable unit with lots of privacy and a great local vibe!

Superhost

The exterior view of the home reveals a two-story structure with a spacious balcony, furnished with chairs and a table. Lush greenery surrounds the entrance, and decorative plants enhance the front yard. A clear blue sky and palm trees frame the scene.

Condo in Lahaina

4.88 out of 5 average rating, 16 reviews

OCEAN Front! Walk to the Beach! Private & Gated!

The best ocean views! Our home is located in a family-friendly, gated community with 30 acres of ocean-front property and a private security guard! Our waterfront home features 3 rooms. Two bedrooms are master suites with Cali-King beds and en-suite bathrooms. Additionally, there is a 3rd-floor space/bedroom, with ocean views, a queen, and a twin XL bed. This 3rd floor is up loft-ladder stairs (photos provided).

Superhost

A black and silver SUV is parked on a dirt road, surrounded by green vegetation. The vehicle features a spacious interior, alloy wheels, and running boards, providing easy access. Sunlight reflects off the windows, highlighting the clean, well-maintained exterior.

Condo in Kaunakakai

4.71 out of 5 average rating, 173 reviews

*VEHICLE INCLUDED! Wavecrest Resort EAST MOLOKAI

TA-075-407-5648-01 THIS UNIT COMES WITH THE ABILITY TO USE OF AN SUV...... UPDATE!!!! We now have dedicated internet!!!!No more bad resort Wi-Fi!!! This unit is located on the island of Molokai. After years as a long term rental, my cozy,semi-private location at Wavecrest Resort is a vacation rental again. Often described as a home away from home this unit will bring a warm feeling to your heart and soul.

Guest favorite

A gated pool area is surrounded by palm trees, with sunlight reflecting off the clear water. Lounge chairs are neatly placed around the pool, creating a relaxed atmosphere. The condo buildings are visible in the background, complemented by a bright blue sky.

Condo in Kaunakakai

4.88 out of 5 average rating, 8 reviews

Palm Breeze Seaside (Molokai Island) Retreat

On Molokai (not island of Maui) Have fun with the whole family at this newly remodeled, first-floor condo with all the essentials on the island of Molokai. Includes a walk-out patio with easy access to a gated pool/cabana area, shuffleboard, tennis courts, a quiet beach area, and views of Maui, Lana’i, and Kaho'olawe. Well-equipped kitchen with brand-new appliances. Handicap-accessible eat-in counter.

Top guest favorite

The outdoor pool area features a large, inviting pool surrounded by palm trees and lush tropical plants. Comfortable lounge chairs are positioned around the pool deck. A small waterfall adds a serene touch to the setting, with sunny skies illuminating the landscape.

Condo in Lahaina

4.98 out of 5 average rating, 184 reviews

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.

Top guest favorite

A sparkling blue swimming pool is framed by palm trees and lounge chairs, offering a scenic view of the ocean. The pool area is complemented by a thatched-roof gazebo, while the clear sky enhances the inviting atmosphere around the water.

Condo in Lahaina

4.96 out of 5 average rating, 248 reviews

Napili Oasis Hideaway, Amazing Oceanview in Maui

Welcome to my beautiful oceanview condo, in one of a kind boutique condominium. Wake up to ocean breeze and view from lanai, watch turtles and sunset on lava rocks, feel at home falling asleep to the sound of the ocean every night 60-seconds walk to Napili beach. Located on the 2nd floor at Napili Shores Resort on West Maui, easy access to world-class beaches, restaurants, shopping and golfing