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Compare 337 Vacation Homes in Paia with updated reviews, rates, and availability.

Kaiholo Hale
Front of property
Kaiholo Hale
3.0 star property
9.4 out of 10, Exceptional, (186)
"A bit dated but honestly was part of its charm. Spotless & utterly comfortable. Great location. Managed well. "
Kaiholo Hale
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Exterior
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
9.8 out of 10, Exceptional, (58)
"After staying here for a 3rd time, I decided to leave a review. This is such a fantastic home in the best location on Maui. We LOVE having the private beach in our own backyard, plenty of space to gather as a family with privacy in the bedrooms if we want it. The teens work out in the fitness center, the kids play in the pool and the adults lay out on the beach, all without leaving! Thank you so much"
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
10.0 out of 10, Exceptional, (42)
"What a view! We watched the sunset every night from the patio. The space was very large and also very well equipped with beach gear. A/C worked great and no issue with any part or the property."
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
Panoramic view from the deck. Master bedroom view is even better !
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
10.0 out of 10, Exceptional, (124)
"The property provided us ample space to spread out and relax"
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Kitchen Area
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
10.0 out of 10, Exceptional, (77)
"We had a wonderful time staying at the Umalu location. It was conveniently located right next to the highway so it was easy access to get around the island. And it was only a 5 minute drive down the street from the beach. The hosts, Kelly and Dan were so nice and made us home made banana bread to welcome us and also shared some great dining locations for us to visit during our stay. "
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Pool
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
10.0 out of 10, Exceptional, (2)
"After looking at dozens of home for rent, we decided on this property and do not regret the decision. It’s beautifully appointed with brand new furniture, plenty of room for a large group (we had 16) and my goodness, that beach across the street, divine! There are several areas to dine, a gorgeous pool with pool and beach toys included, and what felt like a private concierge with the manager (who lives close by). Thank you for an unforgettable vacation with my family. We will cherish the...
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
Living Room - Tile floors, bamboo furniture, and custom redwood throughout
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
10.0 out of 10, Exceptional, (160)
"We loved our stay here - the home is cozy and the views are amazing. We enjoyed paddleboarding with turtles and seeing them not only on the beach and in the water but from the house as well. The owner and property manager were great and responsive, the home is older, but very well kept and clean. Absolutely would stay here again! No AC, but open windows and fans cooled the place down nicely, especially at night. Would highly recommend!"
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Pole House Overlooks West Maui Mountains and Ocean
Mountain to Ocean Views Pole House @ Maui Adventure Villa
9.8 out of 10, Exceptional, (206)
"We were amazed at the warmth and decor and incredible views from this beautiful home We would not hesitate to return. Jeff and Beth"
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Pool with bubblers and hot tub running. One of 3 waterwalls in the background.
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
10.0 out of 10, Exceptional, (28)
"Very clean… all the amenities. Loved the pool, deck and movie room. Kurt was an amazing host! Would definitely be back. "
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
Exterior
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
2.0 star property
10.0 out of 10, Exceptional, (3)
"This is truly an exceptional property, if I could give it 6 stars I would. It had everything you could possibly need for a Maui vacation. The upstairs has a game room equipped with ping pong, air hockey and video games that would rival most arcades. The fitness facility was as well equipped as the fitness center we work out at in Denver. The bedrooms, bathrooms, kitchen and living areas are all beautiful and spacious, way more than enough room for our group of 12. There are tons of beach chairs,...
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
Private gated home with 300 Foot private beach front, beach toys and much more!
Our very own beach
Private gated home with 300 Foot private beach front, beach toys and much more!
10.0 out of 10, Exceptional, (53)
"Are you looking for the premier stay in all of Maui? Look no further than this amazing beach house. We stayed here for 7 days in August, and fell in love with all this place has to offer. The entire house was spotlessly clean, with plenty of towels and toiletries. The bedrooms each have their own climate control, the beds are all super comfortable, and all bedrooms have stunning views of the ocean. We spent a great deal of time watching the waves and turtles from the sitting area off the kitchen...
Private gated home with 300 Foot private beach front, beach toys and much more!
Modern 3 Bedroom Family Friendly Kihei Home Near Beach
Outdoor dining
Modern 3 Bedroom Family Friendly Kihei Home Near Beach
9.8 out of 10, Exceptional, (138)
"Wonderful location with plenty of amenities to make for a great Maui vacation. In-laws booked the 2nd unit next door and we had a wonderful time hanging out on the large deck. Would absolutely book again."
Modern 3 Bedroom Family Friendly Kihei Home Near Beach
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Living area
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
10.0 out of 10, Exceptional, (41)
"We had a fantastic time staying at the Kihei house. Our kids loved having their own pool and we spent hours out there everyday. The house was in a great location, everything was very clean and well taken care of. The host was very responsive when we messaged. Overall a great place to stay!"
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
Elegant private lanai off of the spacious living room
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
9.6 out of 10, Exceptional, (78)
"We came to Hawaii to visit our son and grandchildren who live in Maui. This home was perfect for our needs, well stocked, and the pool area was fantastic."
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
Pool
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
10.0 out of 10, Exceptional, (2)
"If you seek a large home that can accommodate large groups, if you seek close proximity to the most amazing beach - this is the home for you! It feels like Napili Bay is in your front yard! Napili Bay has long been our favorite beach on all of Maui, and now we finally have a home next to it, that we can return and rent each year. We had small kids, teens and adults and the home and management just couldn’t be better. 5 stars all the way around."
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
Panoramic Ocean View Condo on Golf Course close to Beaches
View from our Lanai
Panoramic Ocean View Condo on Golf Course close to Beaches
10.0 out of 10, Exceptional, (7)
"Beautiful property with many upgrades and amazing ocean views. Great proximity to the beach and shops and a very quiet and relaxing location. The place was also very well equipped with cooking supplies, appliances and beach accessories. We would definitely stay here again!"
Panoramic Ocean View Condo on Golf Course close to Beaches
Kapalua Golf Villas by KBM Resorts
Terrace/patio
Kapalua Golf Villas by KBM Resorts
3.5 star property
10.0 out of 10, Exceptional, (3)
"Privacy was very important to me. "
The price is AED 1,316
AED 3,230 total
includes taxes & fees
8 Dec - 9 Dec
Kapalua Golf Villas by KBM Resorts
Spacious Hawaiian home 50 steps from Sugar Beach!
Beach
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, (63)
"Fabulous spot for a family with kids (3, in our case). Quiet neighborhood just a few minutes away from great food and stores. Plenty of space in the house and a cute backyard to boot. Incredibly easy to walk to the beach (crosswalk and access path). Good spot for day trips north and west. A+"
Spacious Hawaiian home 50 steps from Sugar Beach!
BEACHFRONT MAUI KIHEI HOUSE
Breakfast on the upper Lanai with Ocean and property views
BEACHFRONT MAUI KIHEI HOUSE
9.8 out of 10, Exceptional, (150)
"This house was absolutely perfect for our family. We had 10 people staying and we all fit very comfortably. The beds were nice, they have ac units in all of the rooms which was great for our family with different temperature needs. The yard was so much fun for our toddlers to run and play in and the beach is a very short walk away. We all really enjoyed relaxing at the house. We needed a pack and play for our toddler and a newborn and while we brought one we also depended on the one available at...
BEACHFRONT MAUI KIHEI HOUSE
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Our heated pool with the beach just 50 feet past our lava rock wall.
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
9.8 out of 10, Exceptional, (187)
"We were a Party of 11 - we loved the house set up and the space was perfect for our large group - pool and beach access - awesome! "
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Paia

Aston Kaanapali Shores
Exterior
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3349)
"Totally Excellent."
The price is AED 1,190
AED 1,512 total
includes taxes & fees
20 Nov - 21 Nov
Aston Kaanapali Shores
OUTRIGGER Honua Kai Resort & Spa
Exterior
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2627)
"Nice and smooth experience. I recommend it!"
The price is AED 1,154
AED 3,307 total
includes taxes & fees
9 Dec - 10 Dec
OUTRIGGER Honua Kai Resort & Spa
The Westin Ka'anapali Ocean Resort Villas
Exterior
The Westin Ka'anapali Ocean Resort Villas
4.0 star property
8.6 out of 10, Excellent, (1080)
"Loved the shuttle to whalers village. Had to request housekeeping service twice during our stay as our room was missed ?"
The price is AED 1,759
AED 2,075 total
includes taxes & fees
30 Nov - 1 Dec
The Westin Ka'anapali Ocean Resort Villas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.