Holiday rentals with a pool in Maalaea Bay

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Top-rated rentals with a pool in Maalaea Bay

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

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Superhost

Condo in Kihei

4.83 out of 5 average rating, 143 reviews

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!

Guest favourite

Condo in Wailea-Makena

4.97 out of 5 average rating, 107 reviews

Grand Island Paradise on Golf Course w/Ocean Views

🌅 Relax and enjoy sunset ocean views every night! 🏖️We are <1 mile from Wailea Beach! Our home is spacious, in a perfect location, and newly renovated! Inside are 3 bedrooms w/ a King, Queen, 4 Twin, and 2 trundle beds! There are 2 private balconies, private laundry, LARGE kitchen and it's ground level- NO STAIRS! The complex has 2 POOLS and HOT TUBS! Parking for 2+ cars. Super close to Wailea, Makena, Keawakapu! ❤️ We provide more than the average host- (beach & baby gear) ask us about it!

Superhost

Condo in Lahaina

5 out of 5 average rating, 3 reviews

Resort Stay Entire 1Bdr Villa Kaanapali Beachfront

This resort has the most amazing pool on the island, Salt Water Based !! So easy on the skin ;) Olympic size pool about 2.5 Acres with Slide, waterfalls , plunge pool, volleyball. Snorkel Equipment rental , Beach chairs etc. All you need to have a great Hawaiian Vacation with The Family. Awesome Luau on Site every Teus Night! This price is for scenic if avail. Otherwise upgrade is additional if oceanview is what we have for your dates:) Mahalo For coming back to The West Side Best Side!

Superhost

Condo in Kihei

4.82 out of 5 average rating, 264 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.

Guest favourite

Condo in Wailuku

4.89 out of 5 average rating, 108 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!

Superhost

Condo in Kihei

4.81 out of 5 average rating, 245 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.

Guest favourite

Condo in Lahaina

4.97 out of 5 average rating, 103 reviews

2025 Special! Ocean views! Updated+Air Conditioned

At last, you’ve found an extraordinary combination of secluded privacy, breath taking ocean views & magical sunsets. Our split Air Conditioned apartment has been beautifully updated and features a large private bedroom with a King size bed & a Queen sofa sleeper in the living room. The apartment has all new modern furniture, 700 count linens, granite counter tops & stainless steel appliances. Direct water access, 2 pools, hot tubs, Koi ponds, putting greens and more!

Guest favourite

Home in Kihei

4.96 out of 5 average rating, 412 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 favourite

Condo in Lahaina

4.98 out of 5 average rating, 173 reviews

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.

Guest favourite

Home in Kula

4.91 out of 5 average rating, 303 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 10 years with over 1,000 five star reviews. BUT this one, Kula Jewel, burned to the ground in the Maui wildfires in August, 2023. We are in the process of rebuilding a GORGEOUS new home, and we are taking bookings for 2025. Iʻm including some progress photos which I update weekly. The house will be ready before Christmas 2024!!

Superhost

Condo in Lahaina

4.88 out of 5 average rating, 100 reviews

Top Floor Stunner! Highly Upgraded! Feb Open! #414

"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.

Superhost

Condo in Kihei

4.84 out of 5 average rating, 353 reviews

Cheap Cozy Studio- Very active legal vacation zone

Our place is close to the beach, family-friendly activities, Shops of Wailea, many Wailea Hotels: Andaz, Fairmont, Marriott Four Seasons Hotel, etc., restaurants, golf courses, tennis court. You’ll love my place because of the comfy bed, big TV, the views, overlooking pool and palm trees with easy access straight down to pool/jacuzzi/BBQ from your lanai. .