Vacation rentals with a pool in Lahaina

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

Escape and fall in love with “Ka Hale Aloha-The Love Shack” where paradise awaits you....This adventurous hideaway will leave you feeling refreshed, relaxed and more alive!! Experience all the life & Aloha the island of Maui has to offer in your private detached bungalow located on an old 8 acre fruit plantation turned condos, steps to the ocean & walking distance to 2 beaches. Ka Hale Aloha will make you feel like you’re truly living the island life. * Check us out on IG at @thoughtfulstays

4.99 out of 5 average rating, 223 reviews

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.

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, 158 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.

4.93 out of 5 average rating, 150 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.

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.

4.97 out of 5 average rating, 105 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, 279 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.

4.94 out of 5 average rating, 147 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

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.

4.99 out of 5 average rating, 211 reviews

Sunsets and Turtles and Whales, Oh My!

Spectacular ocean views Whales and turtles galore(whale season Nov-March) Great snorkeling Lush tropical landscaping Pool, grills, shuffleboard, laundry room, 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

4.91 out of 5 average rating, 169 reviews

Oceanfront Condo at Napili Bay | Newly Refreshed

Thank you for checking out my newly refreshed OCEANFRONT condo located at the charming Napili Shores resort! ✨ FRESH LOOK, NEW COMFORT ✨ We’ve just given the entire condo a complete update! Enjoy brand-new modern furniture, freshly painted walls, and thoughtfully upgraded fixtures throughout. The entire home feels clean, bright, and beautifully refreshed—offering you an elevated, relaxing space for your ultimate Maui retreat.

4.98 out of 5 average rating, 206 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.

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, 137 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

4.8 out of 5 average rating, 116 reviews

A spacious outdoor area features a private pool with clear blue water, framed by stone landscaping. An arched structure offers shade near the pool, and a red bowl sculpture adds a pop of color. Lush greenery surrounds the space, enhancing the serene environment.

Villa in Kaanapali

Kaanapali Fairway Villa 3BR/3BA.

Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.

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, 620 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

4.92 out of 5 average rating, 147 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

4.93 out of 5 average rating, 420 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!

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

4.96 out of 5 average rating, 469 reviews

Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

4.81 out of 5 average rating, 113 reviews

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

4.87 out of 5 average rating, 123 reviews

Home in Kaanapali

Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr

4.88 out of 5 average rating, 119 reviews

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

Condo rentals with a pool

A serene outdoor dining area features a small table paired with two woven chairs, positioned on a lanai overlooking the ocean. A potted plant sits at the center of the table, while the expansive blue sea and distant mountains create a tranquil backdrop.

4.96 out of 5 average rating, 159 reviews

Pohailani 113 - Vacation West Maui - Gorgeous w/AC

A comfortable living area features a large window with stunning ocean views. The space is furnished with a beige sofa, a wooden coffee table, and a glass dining table. A ceiling fan adds a breezy touch, while sliding glass doors lead to a private balcony.

4.94 out of 5 average rating, 172 reviews

Dream-like ocean views! Steps from the Ocean

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, 152 reviews

Ocean Views- Beachfront- Steps to a Sandy Beach!

A hallway leads to an outdoor area with views of the turquoise ocean and swaying palm trees. The scene is framed by a solid railing, showcasing the tropical coastal environment and vibrant colors of the water, with gentle waves visible in the distance.

4.89 out of 5 average rating, 354 reviews

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

4.99 out of 5 average rating, 189 reviews

Fresh Reno on 8th Floor Studio - Amazing Views

4.98 out of 5 average rating, 124 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!

4.97 out of 5 average rating, 173 reviews

NapiliBayStudio $169nightly guest’s fee included

A small outdoor dining set is positioned on a private lanai, featuring a round table flanked by two cushioned chairs. The backdrop showcases expansive views of the turquoise ocean and a clear blue sky, with gentle waves visible in the distance.

4.89 out of 5 average rating, 103 reviews

Rare 2 King Suites•Oceanfront•Watch Whales&Turtles

Other vacation rentals with a pool

A spacious living area features a comfortable sofa adorned with decorative pillows. A light-colored coffee table is positioned centrally on a patterned rug. The open kitchen is visible in the background, equipped with modern appliances and sleek cabinetry. Bar stools line the kitchen counter.

4.97 out of 5 average rating, 149 reviews

Beautiful Papakea 1 Bedroom with A/C

A dining table set for two, featuring a selection of fresh fruit, pastries, and beverages. The table is positioned on a private lanai with a view of the ocean in the background, complemented by a gentle breeze and soft sunlight.

4.94 out of 5 average rating, 142 reviews

Mahana 1015 - Luxury Oceanfront Condo (1bd/2ba)

5.0 out of 5 average rating, 17 reviews

Kahana Ocean View | Pool, Beach, Private Lanai

5.0 out of 5 average rating, 14 reviews

Condo in Lahaina

Guest Favorite: Beachfront AC, Seals, Honu & Surf

5.0 out of 5 average rating, 15 reviews

A modern living area features a spacious sectional sofa and a woven coffee table, with natural light filtering through large glass doors. A sleek television is mounted, while a small workspace is tucked under the staircase, accented by a decorative wall piece.

Townhouse in Lahaina

87-1 Escape to Paradise at Puamana's Hale Nalu

4.96 out of 5 average rating, 57 reviews

Honokeana Cove Oceanfront w/ Turtle Snorkeling

4.93 out of 5 average rating, 29 reviews

An open balcony view showcases the ocean and horizon, with gentle waves visible. The glass doors lead to the outdoors, where patio furniture offers a place to relax. Sunlight creates a shimmering effect on the water, reflecting the clear blue sky.

Apartment in Lahaina

Beautiful Lahaina Roads Condo