Vacation rentals with a pool in Waihee-Waiehu

4.87 out of 5 average rating, 573 reviews

Guest suite in Wailuku

Poolside Ocean View Retreat- Private Guest Suite

Escape to a relaxed tropical retreat in private villa-style suite featuring its own entrance, ensuite bathroom w/ natural stone shower, coffee station, mini fridge, & outdoor bistro seating. Guests also enjoy access to our lush shared pool area and shared kitchen spaces, creating a boutique island experience designed for comfort, connection, and relaxed Maui living. Centrally located & great for exploring all Maui has to offer. Great hikes and beaches nearby! Maui County Permit BBWK 2019/0003

ValueFamilyParking

4.81 out of 5 average rating, 113 reviews

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

True Hawaiiana charm, comfort, and convenience for your family vacation. Located in the heart of Maui, in historic Wailuku town, with easy access to all parts of the island for all your planned activities. Beaches within 10 minutes drive time in 3 directions and the beautiful West Maui mountains w/ Iao Valley National park behind. After a day of adventure come home to a restful time in the HOT TUB under the bright stars . Walk to boutiquey stores ,Coffee shops, First Friday party w/the locals

ValueFamilyAccuracy

4.97 out of 5 average rating, 261 reviews

A two-story green house is surrounded by lush tropical gardens, showcasing large windows that provide a bright interior. A spacious deck extends from the structure, offering views of the vibrant foliage and the inviting outdoor space.

Cabin in Maui County

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

LocationValueShared spaces

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.

4.98 out of 5 average rating, 124 reviews

Coastal Dream Oceanfront Condo!

Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

FamilyValueAccuracy

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!

Pamela has been hosting two fully permitted listings for the last 12 years with over 1,500 five star reviews. BUT Kula Jewel, burned to the ground in the Maui wildfires in 2023. We have recently completed building the NEW Jewel, and it is GORGEOUS! We just had our first guests stay, and this was their review: "The Jewel is extraordinary! The views are stunning! I’ve stayed in many Air B&Bs. I give her place my highest rating!" Btw, we have not raised our prices. The service fee now shows.

FamilyValueLaundry

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.

LocationValueNearby

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.

LocationFamilyAir conditioning

4.99 out of 5 average rating, 158 reviews

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 Kaanapali

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.

ValueFamilyAccuracy

4.94 out of 5 average rating, 127 reviews

Oceanfront, Ground Floor Condo Steps to Ocean

The perfect Maui vacation awaits you in this oceanfront ground level condo located on the Kana'i A Nalu property centrally located on the island in Ma'alaea Bay. Watch whales (Dec-Mar) directly from the lanai as they play in the harbor and then fall asleep at night to the waves outside the bedroom window. Discover the longest stretch of beach on Maui - 2.5 miles of secluded white-sand stretching from the condo towards Kihei with views of nearby islands of Kaho'olawe, Molokini and Lanai.

FamilyLocationParking

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.

ValueLocationView

4.97 out of 5 average rating, 105 reviews

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

ValueLocationQuiet

4.92 out of 5 average rating, 194 reviews

A clear view of a swimming pool is presented, surrounded by lounge chairs and tropical greenery. Palm trees frame the scene, with the ocean visible in the background under a bright blue sky dotted with clouds.

Condo in Kihei

3BR spacious Condo with Ocean View in top location

Enjoy ocean views and island living from this spacious 1,400 sq ft 3-bed/2-bath condo in the heart of Kihei. Located directly across the street from the beach, you can watch whales from the lanai or relax by the pool and BBQ area. Shores of Maui offers easy access to Kihei’s best beaches, shops, and restaurants, all within minutes. A perfect home base for families and groups looking for comfort, convenience, and the South Maui lifestyle.

LocationFamilyLong stay

Popular amenities for Waihee-Waiehu rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 125 reviews

An open living area features a comfortable red leather sofa with decorative pillows. A dining table with wooden chairs is set nearby, and a well-equipped kitchen can be seen in the background. Natural light illuminates the space, enhancing its welcoming ambiance.

Home in Lanai

The Artists House

ValueFamilyParking

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

ValueFamilyCheck-in

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

ValueLocationBreakfast

4.96 out of 5 average rating, 469 reviews

Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

LocationFamilyLong stay

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

FamilyLocationAir conditioning

4.92 out of 5 average rating, 153 reviews

Home in Kihei

Go for an Ocean Swim From a Fun Beach Villa

FamilyLocationOutdoor spaces

4.87 out of 5 average rating, 123 reviews

Home in Kaanapali

Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr

FamilyValueCheckout

4.88 out of 5 average rating, 42 reviews

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

LocationFamilyPool

Condo rentals with a pool

4.91 out of 5 average rating, 169 reviews

Oceanfront Condo at Napili Bay | Newly Refreshed

LocationValueLaundry

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, 114 reviews

Napili Bay Oceanview Resort Hideaway

ValueFamilyAir conditioning

4.97 out of 5 average rating, 105 reviews

A picturesque view captures a beach at sunset with vibrant orange and purple hues in the sky. Swaying palm trees line the shoreline, where beachgoers can be seen enjoying the golden sand and gently lapping waves. The grassy area near the beach is dotted with lounge chairs.

Condo in Wailea

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

ValueLocationOutdoor spaces

4.99 out of 5 average rating, 165 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

ValueLocationAccuracy

4.98 out of 5 average rating, 137 reviews

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 Kaanapali

Stylish Love Hideaway, Maui Kaanapali Oceanfront

LocationValueOutdoor spaces

A panoramic view of the ocean is framed by lush palm trees, with gentle waves lapping at the shore. The sky is filled with scattered clouds, casting soft shadows on the tranquil water. A railing borders the view, enhancing the sense of openness.

4.99 out of 5 average rating, 110 reviews

Oceanfront Maui - 2 King Suites, AC & Lanai

LocationFamilyGetting around

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

ValueLocationCleanliness

A comfortable lanai features a dining table surrounded by cushioned chairs, with an unobstructed view of the ocean and beach. Lush palm trees frame the scene, while gentle waves reflect the blue sky and distant islands.

4.94 out of 5 average rating, 171 reviews

Absolute Beachfront with Million-Dollar Views!

FamilyLocationIndoor spaces

Other vacation rentals with a pool

4.83 out of 5 average rating, 219 reviews

A distinguished bamboo cottage is elevated on stilts, surrounded by lush tropical vegetation. Wooden decks wrap around the structure, providing access to outdoor seating areas. Large windows offer views of the surrounding greenery, harmonizing the indoor and outdoor environment.

Cottage in Haiku-Pauwela

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

LocationFamilyCleanliness

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

FamilyLocationCheck-in

4.99 out of 5 average rating, 223 reviews

4.89 out of 5 average rating, 212 reviews

Apartment in Kihei

Family-friendly Oceanview beach retreat | AC, Pool

LocationValueGrill

4.94 out of 5 average rating, 199 reviews

Ma'alaea Ocean Front • Whales, Pool & Hot Tub

ValueFamilyTV

4.83 out of 5 average rating, 53 reviews

A spacious outdoor pool surrounded by lush tropical landscaping invites relaxation. The area features sun loungers and an umbrella-shaded seating arrangement. The elegant home is visible in the background with large windows that reflect the bright blue sky.

Farm stay in Maui County

House w/ Ocean Views in Haiku Maui on Road to Hana

FamilyValueSleep quality

4.96 out of 5 average rating, 57 reviews

Honokeana Cove Oceanfront w/ Turtle Snorkeling

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 14 reviews

Condo in Lahaina

Guest Favorite: Beachfront AC, Seals, Honu & Surf

ValueLocationAccuracy