Holiday rentals with a pool in Kahului

4.87 out of 5 average rating, 571 reviews

Guest suite in Wailuku

Poolside Retreat -Private Suite - Ocean Views

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

4.83 out of 5 average rating, 112 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

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, 123 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.

4.93 out of 5 average rating, 419 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.

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.

4.99 out of 5 average rating, 157 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.

4.93 out of 5 average rating, 149 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.

A modern kitchen features sleek white cabinetry and a spacious island, with a view of the ocean visible through large glass sliding doors. Natural light fills the room, and tropical décor adds a welcoming touch, enhancing the seamless transition to the outdoor space.

4.95 out of 5 average rating, 114 reviews

Oceanfront Maui Escape for Two | Private Lanai

THERES NO PLACE LIKE MAUI! OCEANFRONT condo greets you with endless ocean views, open floor plan and the feeling you have just arrived in Heaven! Step out onto the private lanai and you are captivated by the soothing sound of the waves, warm sunny breezes and turtles everywhere! You deserve the BEST and this home offers it! Located in a perfect location far from the maddening crowd yet walking distance to restaurants, shopping, nightlife, and sightseeing tours. APN2380140110057000

A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.

4.99 out of 5 average rating, 277 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

4.96 out of 5 average rating, 183 reviews

A modern kitchen and dining area are visible, featuring a round table set for four with woven placemats and plates. Stainless steel appliances are arranged in the sleek kitchen design, while large sliding glass doors open to reveal views of lush gardens and the ocean beyond.

Condo in Wailea-Makena

A.R.A Retreats: Big Blue Pacific

Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views and when the sun goes down, watch your favorite shows on on our smart tvs!

A scenic outdoor space features a table set for dining, overlooking a vibrant green lawn and an expansive ocean view. Nearby, comfortable seating invites relaxation. The kitchen area is equipped with modern appliances, while a stylish clock adorns the wall.

4.93 out of 5 average rating, 165 reviews

Oceanfront Getaway, Brand New, Steps To Beach

Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.

4.94 out of 5 average rating, 145 reviews

Condo in Lahaina

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

Popular amenities for Kahului 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, 619 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

4.97 out of 5 average rating, 116 reviews

Home in Kihei

Oceanview Townhome • Modern • 2 Min Walk to Beach!

4.96 out of 5 average rating, 469 reviews

Home in Wailea-Makena

Stunning ocean view Villa, Heated pool, Wailea

4.87 out of 5 average rating, 180 reviews

Two hanging chairs are positioned on a private balcony, surrounded by lush greenery and an ocean view. The chairs are adorned with floral accents, inviting relaxation while enjoying the scenic landscape and coastal horizon.

Home in Napili-Honokowai

Oceanfront Paradise with Pickleball gear!

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

4.92 out of 5 average rating, 145 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

4.87 out of 5 average rating, 122 reviews

Home in Kaanapali

Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr

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

Condo rentals with a pool

4.99 out of 5 average rating, 196 reviews

A stunning beach scene captures vibrant sunset colors reflecting off wet sand. Rocky outcrops frame the tranquil waters, while palm trees sway gently in the foreground. Wispy clouds stretch across the sky, adding depth to the evening landscape.

Condo in Wailea-Makena

Romantic, Luxury Retreat w/Ocean View-Couples Only

The modern kitchen features dark cabinetry and a large marble island with seating. Stainless steel appliances, including a refrigerator and microwave, are visible. A bowl of fresh fruit sits on the island, while natural light illuminates the space through ample windows and overhead pendant lighting.

4.98 out of 5 average rating, 190 reviews

Makani A Kai A5 beachfront, pool, a/c, w/d

The sleeping area features a spacious bed with a light-colored quilt and decorative pillows. Large sliding glass doors provide an expansive view of the ocean and palm trees, with soft curtains framing the scenic backdrop.

4.85 out of 5 average rating, 569 reviews

Amazing views at Oceanfront Studio

A dining table set for two overlooks the ocean, featuring a pineapple centerpiece and plates arranged with utensils. The backdrop includes palm trees and scenic water views under a partly cloudy sky.

4.95 out of 5 average rating, 105 reviews

The Beach Hale

A tranquil beach scene is depicted, featuring soft sandy shores that gently meet the rolling waves. Lush greenery lines the coastline, while distant mountains provide a stunning backdrop under a partly cloudy sky.

4.91 out of 5 average rating, 252 reviews

Rare Beachfront Ground floor Oceanview from Lanai!

A comfortable living area features a large flat-screen TV on a wooden media console. Sliding glass doors provide access to the private lanai, showcasing ocean views. A ceiling fan above adds to the airy ambiance, with a cozy coffee table positioned in front of the seating area.

4.97 out of 5 average rating, 118 reviews

Stunning Oceanfront 1bd - Maalaea Kai 315

A scenic view showcases swaying palm trees against a vibrant blue sky, with a glimpse of the ocean in the background. Lush greenery frames a pool area, inviting relaxation, while the buildings provide a residential atmosphere. The beach appears just beyond the manicured lawns.

4.93 out of 5 average rating, 171 reviews

Lovely Oceanfront Condo with pool

4.99 out of 5 average rating, 163 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

Other holiday rentals with a pool

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.

4.97 out of 5 average rating, 103 reviews

Maui Full Oceanfront Paradise

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.

4.99 out of 5 average rating, 222 reviews

Peaceful Maui Bungalow | Ka Hale Aloha-Love Shack

4.97 out of 5 average rating, 427 reviews

A collection of colorful canoes is positioned along the shore, framed by swaying palm trees. The ocean waves glisten under a moody sky, transitioning to sunset hues, while soft clouds add texture to the backdrop.

Guest suite in Kihei

"Dancing Turtle's "Guest Suite"

A modern loft interior features a spacious living area with a light grey sectional sofa adorned with various blue and white throw pillows. A simple wooden dining table with teal seating is visible alongside a kitchen with a white island. Large windows allow natural light, and a decorative wall clock adds charm.

4.97 out of 5 average rating, 199 reviews

Live, Love, Loft in Beautiful Maui

4.94 out of 5 average rating, 142 reviews

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.

Condo in Kaanapali

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

A serene view of the ocean is captured from the lanai, framed by the silhouettes of palm trees. An outdoor table and chairs are positioned for relaxation, with a glimpse of a pool area and lush greenery below.

4.83 out of 5 average rating, 327 reviews

Hello View!

4.94 out of 5 average rating, 136 reviews

A modern kitchen features sleek cabinetry and stainless steel appliances, including a refrigerator and microwave. A light grey tile backsplash complements the white marble countertop, which hosts a built-in stove. Natural light enters through a small window, enhancing the airy space.

Apartment in Kihei

High-end, On Beach, View Balcony, with Pool & BBQ!

A stunning sunset casts vibrant colors across the sky above the ocean. Silhouetted palm trees frame the scene, while distant mountains provide a scenic backdrop. The calm water reflects the hues of pink, orange, and purple, creating a serene atmosphere.