Vacation rentals with a pool in Kahului

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Top-rated rentals with a pool in Kahului

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

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Top guest favorite

A tranquil, heated saltwater pool is surrounded by lounge chairs and palm trees, offering serene ocean views. The pool area is framed by well-maintained grassy spaces, with gentle waves visible in the distance. The scene is set during early morning light, enhancing the peaceful atmosphere.

Condo in Wailea

4.99 out of 5 average rating, 198 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! Mana Kai is a hotel zoned resort in an ideal location, right on the border of Wailea and Kihei! Our condo is designed with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5-star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!.

Top guest favorite

Condo in Wailea

4.99 out of 5 average rating, 122 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and bi-coastal oceanfront views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (806) and includes two-bedroom suites on the world-famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent snorkeling, body surfing, whale watching, scuba diving, paddle boarding, and kayaking literally at your doorstep

Top guest favorite

A refreshing saltwater pool is surrounded by a black metal fence, with lush greenery and palm trees gently swaying in the background. Loungers are positioned nearby on a well-maintained lawn, offering a serene view of the landscape and distant mountains.

Condo in Wailuku

4.98 out of 5 average rating, 153 reviews

Makani A Kai A5 beachfront, pool, a/c, w/d, 2 sups

Halerentals MAK A5 is a completely renovated beachfront condo, with high end materials throughout. RH furniture, cotton sheets, marble shower, gourmet kitchen, & a/c in every room-- just steps away from 3 miles of undeveloped beach! Bright spacious ground floor 1bed/1bath condo with fully stocked kitchen, and views of the beach, bay, & Haleakala volcano. King RH sofa bed in living room for up to 4 guests. Ideal for swimming, SUP, snorkeling, and surfing-- amazing value for families and couples.

Top guest favorite

Condo in Lahaina

4.99 out of 5 average rating, 135 reviews

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 & centrally located next to the Montage Resort. 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, shopping, spas, & several bays/beaches great for snorkeling, surfing, & relaxing, this is the perfect home base.

Top guest favorite

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

4.93 out of 5 average rating, 362 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, 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: "Pamela’s place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! I’ve stayed in many Air B&Bs; I give her place my highest rating!"

Top guest favorite

An open and light-filled living area is featured, showcasing large glass sliding doors that offer views of lush tropical landscaping. A spacious gray sectional is complemented by a cozy chair, and a neutral area rug anchors the space. Decorative elements include the word "ALOHA" on the wall.

Condo in Wailea

5 out of 5 average rating, 117 reviews

*Tropical luxury at South Maui Surf Shack*

South Maui Surf Shack is located in Maui Kamaole. New renovations (Feb 2022) 1bed (King) 2bath + Murphy bed (Queen), beach style condo, over 1050 sq feet! Our fully stocked kitchen gives you the ability to cook your meals or head to any of the nearby restaurants in Kihei or Wailea (we are on the border). You are in the center of it all with the best beaches & golf courses Maui has to offer. We are here to help with absolutely anything you need to make your trip memorable, fun & relaxing!

Top guest favorite

A serene outdoor pool is surrounded by lush tropical landscaping. Lounge chairs are arranged neatly around the water, providing ample seating for relaxation. The pool's clear blue water reflects the sunlight, and a gentle slope leads to a well-maintained grassy area.

Condo in Kihei

4.99 out of 5 average rating, 226 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.

Guest favorite

A serene outdoor area features well-maintained green grass and several lounge chairs positioned to face the ocean. A table with decorative items is visible in the foreground, while palm trees sway gently in the breeze against a clear blue sky, providing a view of the distant mountains.

Condo in Wailuku

4.9 out of 5 average rating, 129 reviews

Oceanfront Condo with Pool and Jacuzzi

Relax in this peaceful gem on Maui. Located on the ground floor, you can walk into the ocean from your back porch. You'll see Turtles on our little secluded beach, amazing sunrises and sunsets over Maalaea Bay, and Whales during whale season! Maalaea Banyan is the only property in the area that includes a pool and jacuzzi. Just 1/4 mile away is Maalaea Harbor featuring snorkel, SCUBA, and sunset boat trips, the world famous Maui Ocean Center aquarium, restaurants and gift shops!

Guest favorite

A spacious room features a king-size bed, complemented by wooden accents and natural light streaming through sliding glass doors. The kitchen area includes a granite countertop with cabinets. A private balcony with chairs overlooks a lush outdoor setting, enhancing the serene atmosphere.

Condo in Lahaina

5 out of 5 average rating, 136 reviews

Napili bay Studio Sept special$99!

Aloha🙏🙏🙏 Corner unit . 50’ vizio TV(Smart) Free WiFi King size bed Ceiling fan AC 18000 BTU Balcony’s chair and table Beach umbrella Beach chairs (2) And cooler Oven Microwave Refrigerator Pots,pans,utensils Coffee maker Complimentary coffee Set of beach towels (2) Set of towels,hand towels Etc Hair dryer Pool/all year around Iron Start up hand soap shampoo,conditioner,lotion Maui book Free parking Bbq area Toaster Blender Sal/pepper Ceiling fan 10 min walk to Napili bay

Top guest favorite

Condo in Lahaina

4.99 out of 5 average rating, 138 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.

Guest favorite

A vibrant outdoor space features a heated private pool surrounded by lush tropical plants and palm trees. Comfortable lounge chairs are positioned by the edge of the pool, while a shaded dining area is set under a patio umbrella. A cascading fountain adds a tranquil element.

Home in Wailea

4.96 out of 5 average rating, 440 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Guest favorite

Condo in Kihei

4.97 out of 5 average rating, 277 reviews

Toast the Sunset in a Dreamy Island Penthouse Loft

Steps to one of the most beautiful Beaches in Maui, this Dreamers loft has everything you need to celebrate and enjoy life. Situated perfectly in Kihei’s most popular area, you can walk to surf classes, beaches, parks, great restaurants, local market and much more. Enjoy the beach, pool, play tennis or simply relax at your retreat, our loft has everything you need to make your stay on Maui unforgettable.