Holiday rentals with a pool in Maalaea Bay

4.83 out of 5 average rating, 145 reviews

Apartment in Wailea

Beautiful Palms At Wailea #608-2 BR/2 BA

Beautiful Palms At Wailea Condo, located in the heart of Wailea, surrounded by $mil.homes. 5* location. Vinyl wood flooring & Split Air-Cond. system in hallway & in master-B/R. Fans through-out. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., 2BR/2Ba, wide open floor plan ,2nd. fl.unit. Low rise complex. Very private. Large lanai . Barbecue grills located near entryway of complex. Views from the Club House & Pool.The best place to stay!

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Apartment in Lahaina

4.97 out of 5 average rating, 114 reviews

60%OFF APRIL-JUNE/25! Ocean views! Air Conditioned

Thank you for checking us out! We have dropped our price 60% for the month of April 2025 to end of June 2025. They are doing re-piping to the building adjacent to us and there will be construction noise Monday to Friday 9:00am to 4:30pm. NO worked to be done evenings, weekends or holidays. You must acknowledge this at time of booking. Most people are at the beach, pool or touring the island during the day so this might be an opportunity for you to stay in an amazing condo for a great price!!!

4.93 out of 5 average rating, 118 reviews

Luxe Oceanview 2B2B Escape w/AC Near Beach & Shops

Location and Quality! You will feel the relaxed beach vibes from the very first step walking into this tastefully updated & beach luxe unit. Directly sit across the famous Cove surf spot & in the middle of all, you will be memorized by the ocean waves along with surfers, paddlers and the breathtaking sunset views, and the incredible walk distance to everything Kihei has to offer including activities, shopping, dining, nightlife and more! Experience the best of Maui from our Luxe-design condo!

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Home in Kula

4.92 out of 5 average rating, 325 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!"

4.83 out of 5 average rating, 272 reviews

Sea Views entire 1 Bedroom Apartment Poolside

Unobstructed sea views. Small 16 unit property with Pool outside your door. Remodeled 478 sf sunny and cozy apartment. Queen Bed in master, sofa bed in living room. Island Counter has 3 stools and serves as a computer table. Very convenient location in central Kihei. 3-4 Short blocks to restaurants, marketing, shopping and entertainment at the Triangle. Cove Beach across the street for water sports and surf lessons. Pet Deposit is $800 and refunded 30 days after checkout.

4.89 out of 5 average rating, 115 reviews

Apartment in Wailuku

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!

4.8 out of 5 average rating, 249 reviews

Adorable Romantic Studio

Sweetest studio in Maui. Cute little Queen bedroom with stunning mural, barn doors to bathroom. View of sunrise over Haleakala. Located across from the Cove and Kalama Park. Ideally situated for beaches, surfing, bars, restaurants and shopping all within easy walking distance. In-room fridge and coffee. Communal pool, grill and poolside dining area. Free parking lot behind the building. (GET and TAC taxes inc). Please note that there may be construction in the building 1/12-3/18.

4.82 out of 5 average rating, 130 reviews

Cozy 2 Bedroom Condo with pool near beach

Popular Vacation Rental near Kihei's best beaches! This highly sought after 2 bedroom, 1 bath corner unit at Kalama Terrace is close to Charley Young, Kamaole One, and The Cove beach parks. Located on the top floor, you'll enjoy ocean, Lanai and West Maui Mountain views. This condo is perfect for couples and families with a comfortable King bed and a Queen bed. note: The nightly pricing includes taxes like General Excise Tax 0f 4.712% and Transient Accommodations Tax of 10.25%.

4.98 out of 5 average rating, 183 reviews

Apartment in Lahaina

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.

4.88 out of 5 average rating, 101 reviews

Apartment in Lahaina

Top Floor Stunner! Highly Upgraded! Summer Special

"The Kaleialoha" #414 Maui is open and ready for your arrival! Please come help us rebuild our community! This TOP FLOOR unit has unobstructed Ocean and outer island Views! This beautiful completely remodeled unit will take your breath away! New AC unit in living area! New High end sofa sleeper in living room! Cal King Bed and second TV in bedroom. Bosch Washer and dryer in unit.

4.88 out of 5 average rating, 104 reviews

Tropical Paradise Close to Everything

Aloha Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Located on 5 acres of lush tropical grounds, with open grassy spaces and private walk paths, one of the only heated pools on Maui, private tennis courts, bocci ball court, ping pong, and the ocean directly across the street, Koa Resort is a private oasis in central Kihei.