Vacation rentals with a pool in Lahaina

4.98 out of 5 average rating, 102 reviews

Apartment in Lahaina

Lahaina Shores Ocean Front Luxury Condo 525

WHAT A VIEW! Wake to panoramic Pacific and Lānaʻi views, spectacular sunsets, and the sound of the waves from this beautifully renovated fifth-floor oceanfront studio at Lahaina Shores. Enjoy a king bed, air conditioning, Asian antiques, Polynesian art, and thoughtful comforts throughout. As Lahaina continues its renewal, we are temporarily offering lower rates than usual for an oceanfront stay of this quality. Lahaina Shores itself is beautifully refreshed and there are many places to walk to!

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4.97 out of 5 average rating, 119 reviews

Condo in Lahaina

Ocean View Beach Front Condo- Downtown Lahaina

Welcome to our home away from home in Downtown Lahaina! Wake up to the sounds of the ocean as you step out onto your lanai to take in the oceanfront views of West Maui. Enjoy all that Lahaina Shores Beach Resort offers- completely renovated since the fire 2 years ago and reopened on 7-1-25. Located on Front St, though the area is not as it was due to the fire, Lahaina and its iconic banyan tree are standing strong and rebuilding. Private studio with lush king bed, full kitchen and bathroom.

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4.99 out of 5 average rating, 168 reviews

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.

Condo in Kapalua

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 & located next to The Resort at Kapalua Bay (formerly Montage). 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, spas, & several bays/beaches for snorkeling, surfing, & relaxing, this is the perfect home base.

ValueFamilyShared spaces

4.95 out of 5 average rating, 182 reviews

A lush outdoor garden area is visible, featuring vibrant green grass and tropical plants. A seating arrangement with a table and chairs can be seen under an overhang, framed by a flowering tree. The ocean glistens in the distance beneath a clear blue sky.

Townhouse in Kapalua

Amazing Kapalua ,Stay 7 nights, only pay for 6 !

Our place is close to 3 beautiful beaches, 2 spectacular golf courses, tennis garden, hiking trails, whales, zip line, shops, restaurants, pools, barbecue, and spas. You’ll love our place because of the incredible views from the outdoor garden. It is huge and we call it our living room on the lawn. You'll love the ambiance, neighborhood, people. You will love everything about the Ridge at Kapalua. Our place is good for couples, solo adventurers, business travelers, not suitable for children.

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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, 160 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.

ValueFamilyAccess

4.93 out of 5 average rating, 152 reviews

Cottage in Kaanapali

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.

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4.95 out of 5 average rating, 128 reviews

A balcony table set for two showcases two wine glasses overlooking the ocean. Palm trees frame the view, which features clear blue waters and a distant horizon. Bright sunlight illuminates the scenery, creating an inviting outdoor space.

Hotel room in Lahaina

Romantic Oceanfront Condo at Lahaina Shores

My Oceanfront Condo at Lahaina Shores has warm trade winds and sweeping panoramic views of 3 Hawaiian islands. It has a picture perfect, pristine beach in front of the property with swaying palm trees and white sands. The resort is a classic boutique hotel on Front Street. Nearby is the harbor and the famous Banyan tree. It has a pool, hot tub and a beach lawn. The condo has a serene interior with the ocean as the backdrop. You will not want to leave! Enjoy the Aloha spirit! Mahalo!

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Apartment in Napili-Honokowai

A spacious balcony features a simple dining table surrounded by two chairs, offering an unobstructed view of the ocean. Palm trees frame the scene, while a bottle and glass sit on the table, reflecting the bright blue sky above and the serene water below.

Maui Full Oceanfront Paradise

Indulge in the ultimate Maui getaway at our full oceanfront condo. The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants. For those warm tropical nights, rest easy knowing that the condo is equipped with air conditioning to ensure a comfortable night's sleep. The fully stocked kitchen provides all the essentials for cooking up a delightful island feast.

ValueFamilyCleanliness

4.97 out of 5 average rating, 107 reviews

The lanai offers a table with a blue glass bottle as its centerpiece, surrounded by two comfortable chairs. Vibrant blue surfboards are positioned against the wall, while the ocean gently laps at the shore in the background, framed by swaying palm trees.

4.96 out of 5 average rating, 281 reviews

Soothing Waves with 180° View In Kahana, HI

Valley Isle Resort 306 We are located beachfront with an amazing view of the ocean and sunset. We can look right down into the water and watch the turtles swimming. We offer a full kitchen including poolside barbecue grills. Within a block of our Resort are several restaurants and bars. Our condo has a comfy queen-size wall bed along with a small sofa bed. We offer a well stocked kitchen. The ambiance is soothing and relaxing. Our place is good for couples and solo adventurers.

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4.94 out of 5 average rating, 149 reviews

Condo in Lahaina

Beachfront Resort, Peaceful Mountain View Studio

Come stay at Lahaina Shores 506: - Oceanfront Building: Direct access to a sandy beach, pool, and hot tub just steps from the lobby - Mountain Views: Wake up to stunning sunrises from your 5th-floor lanai - Sunny & Clear: West Maui averages ~290 sunny days/year! - Amenities Nearby: Minutes drive to open spots like the Cannery Mall, Lahaina Gateway Center, & classic restaurants - West Maui: Only ~35 mins from the airport Note: Car recommended to explore the island

ValueLocationCondition

4.99 out of 5 average rating, 162 reviews

The living room features comfortable seating with a light-colored sectional sofa and matching ottoman. A large wall-mounted TV displays a serene beach scene. Natural light streams in through expansive glass doors, offering views of the outdoors and creating an airy atmosphere.

Condo in Kapalua

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, The Resort at Kapalua Bay, 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.

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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.

4.98 out of 5 average rating, 140 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

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Popular amenities for Lahaina rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 621 reviews

The spacious studio features a comfortable bed and a seating area with colorful cushions. Large glass doors provide access to a private balcony with stunning ocean views. A flat-screen TV and a ceiling fan are visible, alongside a wooden dresser and a coffee table.

Home in Napili-Honokowai

Maui direct ocean front . Super private

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4.92 out of 5 average rating, 148 reviews

A wide sandy beach extends along the shoreline, meeting clear blue waters. Guests are seen relaxing under umbrellas, while others stroll along the water's edge. Lush palm trees provide shade in the background, contributing to a serene island atmosphere.

Home in Kaanapali

Beautifully Remodeled 3 Bedrooms/2Bathrooms

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4.88 out of 5 average rating, 120 reviews

The kitchen and dining area feature modern appliances and a large wooden table surrounded by a built-in bench. Natural light enters through the window, illuminating the granite countertops and stylish cabinetry, while a beach-themed artwork complements the tropical surroundings.

Home in Kihei

Chic Villa 2 | Modern Vibes by the Ocean

LocationFamilyAmenities

4.93 out of 5 average rating, 423 reviews

A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.

Home in Kula

Kula Jewel - Pool, Hot Tub & Awesome Views!

FamilyValueBackyard

4.96 out of 5 average rating, 470 reviews

Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

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Superhost

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

ValueFamilyCleanliness

4.82 out of 5 average rating, 114 reviews

Superhost

A spacious living area features comfortable seating arrangements with a sectional sofa and wicker chairs. A large mirror enhances the sense of openness. Two televisions are positioned on opposite walls, and the tiled floor is complemented by natural lighting from multiple windows.

Home in Wailea

Condo in Kihei 2 BR - 2 bath Condo

FamilyValueHospitality

4.88 out of 5 average rating, 119 reviews

Superhost

A tropical outdoor area features lounge chairs beside a heated swimming pool. Palm trees sway in the gentle breeze, with a shaded seating area visible under a pergola. The expansive ocean view is framed by lush landscaping, creating a serene atmosphere for relaxation.

Home in Lahaina

Serene and Peaceful with Heated Pool

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4.88 out of 5 average rating, 42 reviews

Condo rentals with a pool

4.98 out of 5 average rating, 207 reviews

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

LocationFamilyIndoor spaces

4.99 out of 5 average rating, 191 reviews

Fresh Reno on 8th Floor Studio - Amazing Views

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A balcony setting is presented with a round table surrounded by four high-back chairs. Two glasses filled with a red beverage sit on the table. Beyond, lush greenery and palm trees are visible, alongside a view of the ocean and resort buildings.

4.88 out of 5 average rating, 170 reviews

Newly Relisted! Discounted rates. No resort fees

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An aerial view captures the lush green landscaping surrounding the property, featuring palm trees and well-maintained rolling lawns. The ocean sparkles in various shades of blue, while nearby buildings with solar panels are visible, creating a serene atmosphere just steps from the beach.

4.98 out of 5 average rating, 115 reviews

Napili Bay Oceanview Resort Hideaway

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4.98 out of 5 average rating, 132 reviews

Two plush, blue upholstered chairs are positioned beside a round glass-top table adorned with a vibrant floral arrangement. The backdrop features expansive floor-to-ceiling windows offering unobstructed views of the ocean and a clear sky.

Condo in Lahaina

Oceanfront Mahana Resort - Vacation West Maui

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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, 154 reviews

Ocean Views- Beachfront- Steps to a Sandy Beach!

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The living area features a rattan furniture set, including a sofa adorned with tropical print cushions. A glass coffee table rests on tiled flooring, while large glass doors provide views of the lush garden outside. A ceiling fan adds to the open, airy ambiance.

4.92 out of 5 average rating, 182 reviews

Affordable Gem West Maui/NEW AC/Location! Unit 2

ValueLocationIndoor spaces

4.97 out of 5 average rating, 201 reviews

Modern Oceanfront Napili | 1br w/ stunning views

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Other vacation rentals with a pool

Vacation home in Napili-Honokowai

The living area showcases large floor-to-ceiling windows framing ocean views. A comfortable sectional sofa is positioned around a wooden coffee table, with a wall-mounted TV and a rustic cabinet nearby. A ceiling fan adds a cooling touch, and outdoor seating is visible through the glass doors.

Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt

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4.97 out of 5 average rating, 136 reviews

Bungalow in Napili-Honokowai

A charming bungalow is surrounded by lush greenery and tropical landscaping, with tall palm trees framing the entrance. A dark blue SUV is parked in the driveway, positioned beside the front door. Bright sunlight highlights the vibrant plants and landscaping, creating a welcoming atmosphere.

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack

ValueLocationAir conditioning

4.99 out of 5 average rating, 223 reviews

4.98 out of 5 average rating, 127 reviews

A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.

Condo in Maalaea

Coastal Dream Oceanfront Condo!

LocationFamilyKitchen

5.0 out of 5 average rating, 18 reviews

Townhouse in Lahaina

58-4 Oceanfront 2 Bedroom

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5.0 out of 5 average rating, 19 reviews

Kahana Ocean View | Pool, Beach, Private Lanai

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The living area features large windows offering unobstructed ocean views. A spacious gray sectional sofa surrounds a wooden coffee table, complemented by a woven chair. The room is illuminated by natural light, enhancing the light-colored tile flooring and reflecting off the mirror-backed wall.

5.0 out of 5 average rating, 33 reviews

Beachfront on Kaanapali The Mahana 1106!

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Apartment in Napili-Honokowai

Turtles & Tides: Maui Oceanfront Whale Watch - AC

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5.0 out of 5 average rating, 22 reviews