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Vacation rentals with a pool in Molokai

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Molokai

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

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Top guest favorite

A spacious pool area features a clear, inviting swimming pool surrounded by lounge chairs. The two-story building displays a series of balconies, flanked by tall palm trees. The tranquil ocean is visible in the background, contributing to a serene atmosphere.

Apartment in Lahaina

4.99 out of 5 average rating, 267 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.

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, 104 reviews

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views

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.

Top guest favorite

Condo in Lahaina

4.99 out of 5 average rating, 128 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.

A heated pool is surrounded by lounge chairs and features a gentle entry with steps. Tropical landscaping enhances the scenery, and the vibrant colors of flowering plants frame the pool area, contributing to a serene atmosphere in this outdoor space.

Cottage in Lahaina

4.92 out of 5 average rating, 139 reviews

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

Top guest favorite

Condo in Lahaina

4.99 out of 5 average rating, 128 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.

An oceanfront swimming pool is surrounded by palm trees, with clear water reflecting the blue sky. Beach access is visible in the background, providing a serene coastal view. The warm tones of the pool deck complement the vibrant greenery nearby.

Condo in Maunaloa

4.93 out of 5 average rating, 101 reviews

Molokai Premier Condo & Car Special Package

Kepuhi Beach Resort. Newly remodeled extra large 565 sq. ft. condo with breathtaking sunset and ocean views from the lanai. Master bedroom with a queen bed and full bath on main floor. Open bedroom with full bed, and 1/2 bath in the loft. • Fully supplied with all kitchen appliances, utensils, food storage containers, etc. • Fast WI-FI for working vacationers. • Office space niche • Large flat screen smart TV, clothes washer and dryer FREE CAR TO USE WHILE STAYING AT THE CONDO.

A clear swimming pool reflects the sky, framed by tall palm trees swaying gently in the breeze. The ocean is visible in the background, with sandy shores and a rocky outcrop enhancing the serene coastal landscape.

Apartment in Maunaloa

4.95 out of 5 average rating, 113 reviews

Peace of Paradise at Kepuhi Beach Resort #2224

(TA#086363955201) Molokai oceanfront condo. View amazing sunsets, beautiful grounds and occasional whale sightings from our 2nd floor lanai. Updated with custom art, fresh linens, full size futon, gel topper for the king size bed, fully equipped kitchen and vanity areas. Ceiling fans and trade winds will keep you cool and comfortable. Washer/dryer, stereo, flat screen TV, free Wi-Fi all add to your comfort. Spend idyllic days lounging at the beach/pool or off on an island adventure!

Top guest favorite

Condo in Maunaloa

4.98 out of 5 average rating, 254 reviews

Sweet Upstairs Corner Ocean View Studio on Molokai

Top floor corner unit at Kepuhi Beach Resort, on the special island of Molokai....in between Maui and Oahu! Vaulted open ceilings, spacious and airy. Completely remodeled and freshly outfitted. Close to beach and ocean-side pool, views of Kaiaka Rock, ocean surf, vivid sunsets. Fully equipped kitchen, luxurious King sized bed. Fast wireless , 40” SmartTV. Perfect setting to unplug, hike or bike the red dirt trails, explore beaches, and experience Molokai fully.

A spacious studio interior is depicted, featuring a firm, round bed with soft bedding. A large wall-mounted TV is positioned above a wooden dresser. Natural light enters through expansive glass doors, revealing lush greenery outside. A comfortable chair and a desk with a chair are included.

Condo in Lahaina

4.96 out of 5 average rating, 108 reviews

★Island Charm Studio, 10 Minutes to Napili Beach★

This charming studio is a ground floor corner-unit located near the highly renowned Napili Bay beach. It features a firm, round bed and a large wall-mounted TV for optimal relaxation following a long day of island exploration. You will have access to all of the features offered by the Napili Ridge association, including a laundry facility, swimming pool, BBQ area, and free parking. Kitchen is fully stocked with cooking utensils. *This unit does not have AC*

Top guest favorite

Condo in Lahaina

4.99 out of 5 average rating, 135 reviews

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.

A panoramic view of a beach is presented, featuring gentle waves lapping against the sandy shore. Large dark rocks border the water, and the horizon shows a clear blue sky with a few wispy clouds.

Condo in Kaunakakai

4.93 out of 5 average rating, 230 reviews

Welcome to Hotel Molokai, Unit 102...

*This unit is located on the island of Moloka'i, not MAUI. Welcome to Moloka'i, where time slows down and you're able to relax and unwind. Hotel Moloka'i is a hotel convenient located on the outskirts of Kaunakakai town. Whether you're on Moloka'i for business or pleasure, our unit offers you a comfortable place to stay. Enjoy beaches all to yourself, go on hikes and listen to live music at Hiro's 'Ohana Grill.

A courtyard pool features a rounded shape surrounded by a sun-deck. Comfortable lounge chairs are positioned around the perimeter, complemented by lush greenery. A tall building with multiple stories stands in the background, contributing to the serene atmosphere of the space.

Condo in Lahaina

4.87 out of 5 average rating, 120 reviews

Stunning Oceanfront, Sunset and Marine Life Views

There's no denying it. The ocean brings us both joy and tranquility that truly soothes the soul. Walker's Paradise Maui welcome's you to come enjoy the breathtaking views, fall asleep and wake up to the sounds of the ocean, watch the most majestic sunsets from the lanai and feel the sea breeze in our beautifully appointed studio condo located at The Valley Isle Resort.

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Popular amenities for Molokai rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A living area features a spacious couch and a matching armchair arranged around a low table. A modern kitchen area with dark cabinetry and stainless appliances is visible, along with decorative artwork on the walls. Natural light fills the space through large windows.

Home in Kaunakakai

4.95 out of 5 average rating, 44 reviews

Getaway at Molokai Shores “June-Aug promo rates”

A light-filled living area features a comfortable sectional sofa adorned with accent pillows. A coffee table sits on a soft area rug, while a dining table and chairs are positioned in the corner. Iconic walls and bamboo flooring complement the space.

Home in Maunaloa

4.89 out of 5 average rating, 76 reviews

Tranquility on West Moloka'i

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.

Home in Lahaina

4.97 out of 5 average rating, 37 reviews

Mahalo Pono @ Ka 'anapali Royal

Top guest favorite

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.

Home in Lahaina

5 out of 5 average rating, 31 reviews

Newly Remodeled Cottage

Top guest favorite

A spacious living area features comfortable seating arranged around a glass-top coffee table. Light-colored walls and tropical decor create a calming ambiance. The kitchen and dining area are visible in the background, showcasing modern appliances and a dining table for shared meals.

Home in Lahaina

5 out of 5 average rating, 14 reviews

Your Beachfront Island Home Awaits! #1A2

An open-concept living space showcases a spiral staircase and a dining area with a wooden table surrounded by rattan chairs. Two woven pendant lights illuminate the room, which features a comfortable sofa with neutral-toned cushions and light flooding in from large windows.

Home in Lahaina

4.92 out of 5 average rating, 12 reviews

3BR/3BA Pualei Beach House

A scenic view captures lush greenery and colorful tropical flowers, enhancing a vibrant landscape. A faint rainbow arcs over rooftops, with the ocean visible in the background. A community swimming pool is situated nearby, surrounded by palm trees and villas.

Home in Lahaina

5 out of 5 average rating, 7 reviews

Luxury Panoramic Ocean Views!

Home in Lahaina

4.8 out of 5 average rating, 20 reviews

ICC 13 Beautifully Furnish Kaanapali Cottage

Condo rentals with a pool

A large swimming pool is surrounded by lush green landscaping and palm trees, offering a serene atmosphere. The clear blue water reflects the bright sky above, creating a tranquil setting for relaxation. Soft lounge areas and access paths are visible near the poolside.

Condo in Maunaloa

4.93 out of 5 average rating, 41 reviews

Molokai Island Paradise

A large swimming pool is surrounded by lounge chairs, with palm trees gently swaying nearby. The clear blue water reflects the bright sky, creating a serene atmosphere. Ocean views can be seen in the distance beyond the pool area.

Condo in Lahaina

4.96 out of 5 average rating, 120 reviews

Oceanview Maui Condo, Turtles, Whales, Rainbows

A spacious pool area is highlighted by clear blue water, reflecting the bright sky above. Lush palm trees surround the pool, while lounge chairs are neatly arranged around the space. Tiki huts offer shaded seating, creating a relaxing atmosphere near the ocean.

Condo in Lahaina

4.91 out of 5 average rating, 208 reviews

Penthouse Studio near Lahaina , Kaanapali ,Kapalua

A sliding glass door opens to a private balcony with a wooden table and chairs overlooking the ocean. The shoreline and distant sailboats are visible, framed by swaying palm trees, creating a serene coastal view.

Condo in Kaunakakai

5 out of 5 average rating, 16 reviews

Molokai Resort with Ocean and West Maui views

Top guest favorite

A shimmering pool reflects the clear sky, surrounded by lush greenery and swaying palm trees. The pool area is enclosed by concrete walkways, providing easy access to the soothing waters and the picturesque ocean view beyond.

Condo in Maunaloa

5 out of 5 average rating, 28 reviews

Lovely condo w/pool walking distance to the beach

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, 316 reviews

TOP FLOOR!!!! Oceanfront, free Wi-Fi, free parking

An oceanfront pool is surrounded by palm trees, offering a refreshing escape. Sun loungers are arranged around the pool, providing space to relax. The scenic view includes the ocean and distant islands under a partly cloudy sky.

Condo in Kaunakakai

4.93 out of 5 average rating, 70 reviews

Molokai Top floor Oceanfront Condo! Best Views!

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

4.89 out of 5 average rating, 9 reviews

Palm Breeze Seaside (Molokai Island) Retreat

Other vacation rentals with a pool

An ocean view is captured from the balcony, showcasing waving palm trees against a clear blue sky. The calm water reflects distant mountains, while the lush greenery borders the shoreline, creating a serene coastal scene.

Condo in Kaunakakai

4.87 out of 5 average rating, 39 reviews

Oceanfront true 2 bedroom w/lanai on Molokai

A large swimming pool is surrounded by lounge chairs, palm trees, and lush greenery. The water is clear and reflects the blue sky, creating a refreshing atmosphere. Shade canopies are visible in the background, providing relaxation spots near the pool area.

Condo in Maunaloa

4.98 out of 5 average rating, 40 reviews

Relax: Molokai isle condo by Pristine beaches #114

Top guest favorite

A rectangular swimming pool is bordered by palm trees and manicured greenery. A dolphin design is visible at the center of the pool, while lounge chairs are placed around the perimeter. The tranquil ocean and distant mountains are visible under a clear blue sky.

Condo in Kaunakakai

4.97 out of 5 average rating, 76 reviews

Molokai Island Retreat - Amazing Summer Deals!

Top guest favorite

A tranquil outdoor setting features a wooden table adorned with a bowl of candles, glowing softly. In the background, palm trees silhouette against a vibrant sunset over the ocean, creating a serene and inviting atmosphere.

Apartment in Maunaloa

5 out of 5 average rating, 19 reviews

Hale Bali - Includes Taxes and Vehicle

A spacious oceanside swimming pool is surrounded by palm trees, with clear blue water reflecting the sky above. Lounge chairs are positioned nearby, offering a place to relax. The pool area leads to views of the ocean, enhancing the coastal atmosphere.

Condo in Maunaloa

4.81 out of 5 average rating, 16 reviews

Beachfront!! Seabreeze! Sunsets, Pool, Adventure

A sparkling pool is framed by lush greenery and tall palm trees. The area is bathed in natural light, highlighting clear blue skies and fluffy white clouds. A covered cabana is visible to one side, offering a shaded seating area for relaxation.

Condo in Kaunakakai

4.74 out of 5 average rating, 80 reviews

Hawaiian Hibiscus ~ Beautiful Oceanfront Condo!

A shaded patio area features a glass-topped table surrounded by metal-framed chairs, offering direct views of the ocean and palm trees swaying gently in the breeze. Lush green grass stretches toward the shoreline, creating a serene outdoor space.

Cottage in Maunaloa

4.95 out of 5 average rating, 21 reviews

Oceanfront/Stunning Views, Premium Pool Access

A kitchen area is presented with dark wood cabinetry and a stainless steel refrigerator. Counter space features a sink, coffee maker, and small kettle, complemented by a dishwasher and a microwave. Cleaning supplies and a dishcloth are visible on the counter.

Apartment in Kaunakakai

4.79 out of 5 average rating, 95 reviews

Molokai sunsets

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