
Holiday rentals with a pool in Maalaea Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Maalaea Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Romantic Beachfront Getaway
Your beachfront escape awaits... This is the perfect spot for your romantic getaway! Right on the beach, you'll enjoy days in the sun, romantic meals dining on the private garden lanai with views of the azure Pacific and nights falling asleep in the luxurious canopy bed listening to the ocean waves lapping at the shore. Just 30 steps to the white sand beach and warm Pacific from both the private garden lania and front door! This truly is a magical spot. Newly remodeled and updated with all the amenities (everything is brand new). You'll enjoy luxury accommodations at a fraction of what you would pay elsewhere. Maalaea Bay is perfectly located and central to the entire island so it's easy to get out and explore... Watch the sunrise from high atop the clouds at the 10,000 ft. summit of Haleakala Volcano (about 45 minutes to the summit). Shop the luxury stores of Wailea (about 20 minutes away). If it is snorkeling, fishing or whale watching that interests you, just walk 5 minutes to Maalaea Harbor and jump on one the many different boat tours leaving throughout the day. Craving a little nightlife? Lahaina is only about a 20 minute drive away. I hope you can come and stay to enjoy what I believe to be one of the best spots in Maui. See you soon !
4.81 out of 5 average rating, 460 reviews
Grnd Floor 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. Split A/C. Upgrades include: travertine flooring, custom kitchen and bathroom cabinetry, granite counter-tops, new stainless appliances, and stone/glass shower. Meticulously maintained grounds along with a refreshing swimming pool and grilling area from this ground floor unit.
4.95 out of 5 average rating, 108 reviews
Private Poolside Oasis & 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
4.84 out of 5 average rating, 530 reviews
Makani A Kai A5 beachfront, pool, a/c, w/d
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.
4.98 out of 5 average rating, 192 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, 125 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, 422 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 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.
4.93 out of 5 average rating, 167 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, 221 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, 163 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, 128 reviewsPopular amenities for Maalaea Bay rentals with a pool
House rentals with a pool

3B2B w/HotTub FamilyComfort HawaiianaCharm Central
4.82 out of 5 average rating, 114 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
Go for an Ocean Swim From a Fun Beach Villa
4.92 out of 5 average rating, 153 reviews
Beautifully Remodeled 3 Bedrooms/2Bathrooms
4.92 out of 5 average rating, 148 reviews
Serene and Peaceful with Heated Pool
4.88 out of 5 average rating, 42 reviews
Maalaea Kai 307 - Maui Prime Oceanfront
4.98 out of 5 average rating, 57 reviews
Oceanview Home with Private pool and hot tub
4.94 out of 5 average rating, 50 reviewsApartment rentals with a pool

*OCEANFRONT**PRISTINE Remodel*UNINTERRUPTED 180°
4.92 out of 5 average rating, 191 reviews
3BR spacious Condo with Ocean View in top location
4.92 out of 5 average rating, 197 reviews
Oceanfront, Ground Floor Condo Steps to Ocean
4.94 out of 5 average rating, 128 reviews
Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
4.99 out of 5 average rating, 232 reviews
Sugar Beach Renovated 10% Discnt on 7 days Booking
4.9 out of 5 average rating, 125 reviews
Escape to Sugar Beach / Ocean Views
4.99 out of 5 average rating, 122 reviews
2BR 2Bath - Oceanfront Remodeled Condo!
4.96 out of 5 average rating, 129 reviews
Oceanfront Panorama: Newly Refreshed 3rd Floor Gem
4.97 out of 5 average rating, 132 reviewsOther holiday rentals with a pool

Maalaea Beachfront Resort
4.94 out of 5 average rating, 108 reviews
Kaanapali Fairway Villa 3BR/3BA.
4.8 out of 5 average rating, 117 reviews
The Whale Watch 208-Oceanfront Kihei
4.88 out of 5 average rating, 139 reviews
Hawaiian DreamTemple- Tropical Oasis BBPH20120004
4.83 out of 5 average rating, 220 reviews
Mana Kai Palms Oceanfront Condo: Keawakapu Beach
4.97 out of 5 average rating, 106 reviews
"Dancing Turtle's "Guest Suite"
4.97 out of 5 average rating, 428 reviews
Hello View!
4.83 out of 5 average rating, 333 reviews
Can be 2 Units! Modern On Beach Ocean View Balcony
4.86 out of 5 average rating, 476 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
- Black Rock Beach
- Big Beach
- Black Sand Beach
- Haleakala National Park
- Old Lahaina Luau
- Ka'anapali Golf Courses
- KOA Resort
- Kihei Kai Nani
- Aston Mahana at Kaanapali
- Kamaole Beach Park II
- PacWhale Eco-Adventures
- Maui Arts & Cultural Center
- Maui Ocean Center
- Hāmoa Beach
- Kahana Beach





