Vacation rentals with a pool in Lahaina

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Top-rated rentals with a pool in Lahaina

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

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Top guest favorite
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.
Condo in Lahaina
4.95 out of 5 average rating, 146 reviews

Ocean Views- Beachfront- Steps to a Sandy Beach!

Views! Views! Views! From the moment you enter Valley Isle unit 110 you will be mesmerized with ocean views from every room. This corner unit is located on the 1st floor and has direct access, steps to a sandy beach. Watch rainbows, turtles or whales from the spacious Lanai, a comfortable scenic space where you can spend your mornings, days or evenings, located within 15 feet from the ocean. Bedroom sliding door opens to tranquil sound of the ocean, doz-off with open doors to the sound of waves.

Top guest favorite
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.
Bungalow in Lahaina
4.99 out of 5 average rating, 217 reviews

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

Top guest favorite
A light-filled living area showcases a beige couch and two patterned chairs, positioned around a wooden coffee table. Floor-to-ceiling windows reveal expansive ocean views, allowing natural light to enhance the space. A ceiling fan adds to the comfort, while a mounted TV is visible on the sideboard.
Condo in Lahaina
4.96 out of 5 average rating, 156 reviews

Whales Watch: Luxe Beachfront-180° Ocean views/AC!

Watch Whales breach during migration & sea turtles and sail boats sailing by while snuggled up in your dreamy, oceanfront kingsize bed with luxurious 600 count cotton sheets! If you love swimming with the turtles and the sound of the ocean, then this is the place for you. Luxuriously remodeled, very secluded corner unit, your Maui hideaway is just 15 feet from the ocean with unbeatable, 180 degrees ocean views. Located on the 5th floor of Valley Isle Resort in Kahana (Within the Hotel Zone).

Top guest favorite
The image captures the exterior of Villa 1615, set within a lush green landscape. Palm trees and other tropical plants surround the two-story villa, which features multiple balconies. The expansive ocean view is visible in the background, highlighting the natural beauty of the location.
Townhouse in Kapalua
4.96 out of 5 average rating, 228 reviews

Spectacular views, prime location Kapalua, Maui.

Prime Kapalua location this stylish, romantic two-level villa offers elevated panoramic ocean views. Wake in a luxurious California King bed to stunning Pacific sunrises and fall asleep to the soothing sound of ocean waves. Relax on your private upstairs lanai or spacious patio and take in the breathtaking views. Walk to beaches, scenic trails and dining. Peaceful, magical- your perfect Maui escape. A/C on both levels and bright, airy interiors, this villa is a tranquil upscale Maui retreat.

Top guest favorite
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 Lahaina
4.96 out of 5 average rating, 181 reviews

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.

Top guest favorite
An inviting outdoor living area features wooden seating arrangements adorned with plush cushions. Lush greenery surrounds the space, and decorative string lights create a warm ambiance overhead. A shaded daybed offers a comfortable spot for relaxation amid the tropical landscape.
Cottage in Lahaina
4.93 out of 5 average rating, 148 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
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.
Condo in Lahaina
4.99 out of 5 average rating, 148 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.

Top guest favorite
Condo in Lahaina
4.95 out of 5 average rating, 153 reviews

Kaanapali Fairway Vista - Legal STR Hotel Zoned

Escape to a Slice of Paradise – Where the Fairway Meets the Ocean. This beautifully appointed condo offers the best of Kaanapali living, featuring a prime golf course front position with serene, sweeping views and a sparkling partial ocean view that will take your breath away. Wake up to the sight of golfers setting off on the world-renowned Kaanapali Golf Courses. In the afternoon, relax on your private lanai and watch the sunset paint the Pacific Ocean in hues of gold and orange.

Guest favorite
Condo in Lahaina
4.93 out of 5 average rating, 131 reviews

Oceanfront 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

Top guest favorite
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 Lahaina
4.99 out of 5 average rating, 157 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.

Top guest favorite
A scenic view captures the sunset over a lush landscape, with a pool reflecting the colorful sky. Tall trees frame the scene, and the distant ocean is visible beneath the dramatic clouds. The vibrant greens of the surrounding vegetation provide a serene backdrop.
Cottage in Makawao
4.99 out of 5 average rating, 236 reviews

Rustic Upcountry retreat with breathtaking views!

Maui County Permits BBMP2019/0006 & SUP2 2019/0003 This is a BnB not a STRH Owners live on property At this time we are hosting to guests 12 or older. This property is terraced so not optimal for young children. This is a non smoking property. No smoking is allowed. Use of the pool, hot tub and dry sauna are private when reserved with our private calendar. Mahalo!

Top guest favorite
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.
Condo in Lahaina
4.99 out of 5 average rating, 123 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 Lahaina rentals with a pool

When is the best time to visit Lahaina?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$73,168 GYDG$71,495 GYDG$62,297 GYDG$164,732 GYDG$167,450 GYDG$157,833 GYDG$145,499 GYDG$114,142 GYDG$75,467 GYDG$70,032 GYDG$78,394 GYDG$75,467 GYD
Avg. temp23°C23°C23°C24°C25°C26°C27°C27°C27°C26°C25°C24°C

Quick stats about vacation rentals with a pool in Lahaina

  • Total vacation rentals

    Explore 340 vacation rentals in Lahaina

  • Nightly prices starting at

    Lahaina vacation rentals start at G$4,181 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    190 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    330 of Lahaina vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lahaina rentals

  • 4.8 Average rating

    Lahaina stays are highly rated by guests—averaging 4.8 out of 5!

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