
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.

Makani A Kai A9 romantic beachfront Maui, pool,a/c
Halerentals MAK A9 is a romantic and newly renovated beachfront condo, centrally located for day trips around the island, and off the beaten tourist path. Cool A/C in every room and smart home controls-- just steps away from 3 miles of undeveloped beach! Bright spacious ground floor 1bed/1bath condo- with fully stocked kitchen, new 75" SmartTV and views of the beach, bay, & Haleakala volcano. Ideal for swimming, paddle boarding, snorkeling, and surfing-- amazing value for families and couples.
4.97 out of 5 average rating, 201 reviews
Beautiful Oceanfront Condo- Great View, A/C,Wi-Fi
The convenient location in Maalaea leaves you minutes away from beautiful beaches, restaurants, and all Maui destinations. An open layout consisting of 1 bedroom and 1 bath gives an expansive feel to this exquisite unit. Central A/C. Luxury upgrades include: luxury plank flooring, custom kitchen and bathroom cabinetry, granite counter-tops, new stainless appliances, stone flooring and stone/glass shower. Meticulously maintained grounds along with a refreshing swimming pool and grilling area.
4.99 out of 5 average rating, 204 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.
4.98 out of 5 average rating, 124 reviews
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.
4.93 out of 5 average rating, 420 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.
4.94 out of 5 average rating, 127 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
4.95 out of 5 average rating, 115 reviews
Oceanfront Condo on magic Sugar Beach - Ocean View
•EAST/SOUTH MAUI IS OPEN FOR BUSINESS AND WELCOMING TOURISM• Life is sweet on Sugar Beach. Our oceanfront condo is fewer than 100 steps to a world-class beach that stretches for 5 miles. The smooth sand, gentle waves, and warm water create the ideal swimming experience. And when you are ready to come in, you can relax on our private beachfront lawn with your own lounge chair, table, and umbrella. Or maybe you prefer the pool? It’s perfectly maintained and private.
4.93 out of 5 average rating, 220 reviews
Ocean Front With Ocean View! AC, King Bed, 2 Bath!
E Komo Mai to our remodeled oceanfront unit with stunning ocean view at the Nani Kai Hale. Feel the ocean breeze, listen to the waves, and watch the whales and sunsets from our tranquil, oceanfront condo. From our comfortable lanai seating you have view of the Islands of Molokini, Kahoolawe and Haleakala while enjoying your morning coffee, evening cocktail, or anytime meal. Walk along the beach and experience beautiful sunsets framed by swaying coconut palms.
4.93 out of 5 average rating, 161 reviews
Sugar Beach Renovated 10% Discnt on 7 days Booking
Sugar Beach Resort sits steps away from the Pacific Ocean in North Kihei and a 5-mile white sandy beach that fronts the property. Guest enjoy taking morning and sunset beach walks while enjoying the panoramic view of Pacific Ocean. Sugar Beach is centrally located, minutes away from Lahaina, Kapalua, downtown Kihei, Wailea, north shore/Paia and some of Maui's famous beaches, renowned golf courses and Maalea Harbor where the Maui Ocean Aquarium is.
4.9 out of 5 average rating, 124 reviews
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.
4.92 out of 5 average rating, 194 reviews
Oceanfront Maui - 2 King Suites, AC & Lanai
Wake to panoramic ocean views from this fifth-floor, direct-oceanfront Maui retreat. Watch sea turtles below from your private lanai and whales during the winter season. The condo features two private king suites, two bathrooms, air-conditioning, a full kitchen and space for up to six guests. Walk to Maalaea Harbor, Maui Ocean Center and nearby beaches, then return for dinner overlooking the water.
4.99 out of 5 average rating, 110 reviews
Oceanfront Spectacular Condo
Escape to this ground floor beachfront unit for the ultimate relaxation. Extensively remodeled kitchen and bathroom with new flooring, ceiling fans, and split A/C in living room and bedroom. Wake up to the calming sounds of the sea, watch whales from your living room, and share the beach with sea turtles. Enjoy direct access to the grassy area and beach, basking in abundant sunshine.
4.96 out of 5 average rating, 125 reviewsPopular amenities for Maalaea Bay rentals with a pool
House rentals with a pool

3B2B w/HotTub FamilyComfort HawaiianaCharm Central
4.81 out of 5 average rating, 113 reviews
Stunning ocean view Villa, Heated pool, Wailea
4.96 out of 5 average rating, 469 reviews
Condo in Kihei 2 BR - 2 bath Condo
4.88 out of 5 average rating, 119 reviews
Chic Villa 2 | Modern Vibes by the Ocean
4.88 out of 5 average rating, 120 reviews
Beautifully Remodeled 3 Bedrooms/2Bathrooms
4.92 out of 5 average rating, 147 reviews
Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr
4.87 out of 5 average rating, 123 reviews
Maalaea Kai 307 - Maui Prime Oceanfront
4.98 out of 5 average rating, 57 reviews
Serene and Peaceful with Heated Pool
4.88 out of 5 average rating, 42 reviewsApartment rentals with a pool

Cozy Beach Condo Ocean & Mountain View’s
4.99 out of 5 average rating, 222 reviews
*Last Minute Deal*Oceanfront Maui's Sugar Beach!
4.86 out of 5 average rating, 168 reviews
Oceanfront Getaway, Brand New, Steps To Beach
4.93 out of 5 average rating, 165 reviews
Rare Beachfront Ground floor Oceanview from Lanai!
4.91 out of 5 average rating, 253 reviews
2BR 2Bath - Oceanfront Remodeled Condo!
4.96 out of 5 average rating, 129 reviews
Lovely Oceanfront Condo with pool
4.92 out of 5 average rating, 174 reviews
Hello View!
4.83 out of 5 average rating, 328 reviews
Oceanfront Bliss Pool & Stunning Views Hono Kai C3
4.86 out of 5 average rating, 138 reviewsOther holiday rentals with a pool

Maalaea Beachfront Resort
4.95 out of 5 average rating, 105 reviews
Poolside Ocean View Retreat- Private Guest Suite
4.87 out of 5 average rating, 573 reviews
Family-friendly Oceanview beach retreat | AC, Pool
4.89 out of 5 average rating, 212 reviews
High-end, On Beach, View Balcony, with Pool & BBQ!
4.94 out of 5 average rating, 138 reviews
Oceanfront Mana Kai Penthouse..Heaven meets Earth!
4.96 out of 5 average rating, 142 reviews
Oceanfront Condo. Pool & Spa, 1 Br.
4.87 out of 5 average rating, 334 reviews
Ocean front! Listen to the waves all day and night
4.81 out of 5 average rating, 172 reviews
Direct Oceanfront Condo Sugar Beach Resort Kihei
5.0 out of 5 average rating, 21 reviewsDestinations to explore
- Family-friendly rentals Maalaea Bay
- Apartment rentals Maalaea Bay
- Waterfront rentals Maalaea Bay
- Beachfront rentals Maalaea Bay
- Rentals with a sauna Maalaea Bay
- Flat rentals Maalaea Bay
- Rentals with beach access Maalaea Bay
- Rentals with a hot tub Maalaea Bay
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Maui
- Kaanapali Beach
- Lahaina Beach
- Whalers Village
- Maui Vista Condominium
- Wailea Beach
- Polo Beach
- Honolua Bay
- Kapalua Bay Beach
- Big Beach
- Black Rock Beach
- Black Sand Beach
- Haleakala National Park
- Old Lahaina Luau
- Ka'anapali Golf Courses
- Kihei Kai Nani
- KOA Resort
- Kamaole Beach Park II
- Aston Mahana at Kaanapali
- Maui Ocean Center
- Maui Arts & Cultural Center
- PacWhale Eco-Adventures
- Hāmoa Beach
- Kahana Beach





