Wailea-Makena Vacation Rentals

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Browse Select Wailea-Makena Vacation Homes

DISCOUNTED JUNE SPECIAL Oceanfront Private Home

9.8 out of 10, Exceptional, (99)
"We spent a blissful week in this beautiful home and the views cannot be beat! We saw whales practically every time we looked out at the ocean and the magical sunset views make this property a must stay. The beach is just steps away while also having the luxury of your own private plunge pool. The house is fully stocked and Janna was a fabulous host. We can’t wait to come back! :)"
DISCOUNTED JUNE SPECIAL Oceanfront Private Home

CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal

9.8 out of 10, Exceptional, (74)
"Great property with perfect location, very relaxing. It was a short driving distance to beaches, restaurants, shops- less than five minutes. Pool is not heated but warms up in the afternoon (during winter). "
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal

Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

10.0 out of 10, Exceptional, (84)
"The location of the house is in a peaceful neighborhood just a short drive from the beach. It was great to be able to chill out after the day's adventure without being too close to the resorts and town. The house itself was spacious and had everything we meeded. The hosts were great and very responsive. Next time we're in Maui, we'll be back! "
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

10.0 out of 10, Exceptional, (92)
"Very rare to find a Ho Olei unit with 4 bedroomsWas a garden view, but so convenient to pool and beach. Beautiful unit and we had a great stay. Stocked well for all beach and pool activities as well"
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

Wonderful Wailea Condo Lanai Water Views

3.0 star property
9.4 out of 10, Exceptional, (3)
"We had such an amazing stay! Prior to arrival we were provided with all the information we needed to make arrival easy and make our stay feel like home. This property had everything we could possibly need and was so clean. Like squeaky clean! And the view!! We stayed in December and we could see whales from the lanai! There are some great restaurants and a chocolate shop nearby that we walked to. We also walked to a luau at a nearby resort. We would absolutely stay here again"
Wonderful Wailea Condo Lanai Water Views

Fabulous views! Exclusive pool, spa and private 1 acre yard.

9.8 out of 10, Exceptional, (130)
"Love the location, close to beach but you will need a car. Pool is great for adults and kids, it has nice steps at either end. Lots of stairs so be aware, fine for us but maybe not for everyone.Best view ever and sunsets are spectacular!we loved it. "
Fabulous views! Exclusive pool, spa and private 1 acre yard.

Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View

10.0 out of 10, Exceptional, (66)
"stayed for one week with family and enjoyed the place very much. The host is very attentive and quick to respond to all questions/requests. We will come back."
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View

Maui Breeze Retreat at Ho'olei! Openings May 12-17, July 19-29 & Aug 22-Sep 14!

10.0 out of 10, Exceptional, (129)
"The property is clean and the property management response to several request was excellent."
Maui Breeze Retreat at Ho'olei! Openings May 12-17, July 19-29 & Aug 22-Sep 14!

WOW! Stunning Ocean Views, Large Deck &Luxury Beds

10.0 out of 10, Exceptional, (47)
"Everyone in our party wanted adventure. None of us wanted a "sit at the beach" vacation. This house helped us accomplish that. The location was perfect - we were able to get everywhere we wanted to around the Island super conveniently and still walk to dinner! The house was convenient, comfortable, and quiet. All in all our group had a lovely experience."
WOW! Stunning Ocean Views, Large Deck &Luxury Beds

Kula Luxury Retreat With Stunning Ocean & Mountain Views!

10.0 out of 10, Exceptional, (70)
"KeoKea ranch is beautiful. The hosts are super responsive and very nice. If you like quiet and incredible views and some four leggeds to entertain you, just do it!"
Kula Luxury Retreat With Stunning Ocean & Mountain Views!

Maui Designer Beach Villa, Wailea, Ho'olei 39-2

9.6 out of 10, Exceptional, (25)
"What a great location! We loved the space and enjoyed our family time together in the unit and at the pool and beach! Thank you! It was perfect for all of us! "
Maui Designer Beach Villa, Wailea, Ho'olei 39-2

PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

9.8 out of 10, Exceptional, (71)
"Home exceeded our expectations. Private beautiful backyard and clean home. Quick access to everywhere we needed to go and had chairs and towels for the beach. Highly recommend this property! "
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

Very Best Deluxe Ocean View...Panoramic View....First Class!!

10.0 out of 10, Exceptional, (143)
"The property is wonderful the view is amazing. The sunsets are breathtaking. The home is a perfect place to just relax and enjoy. The home is well provided . I can’t say enough about how much we loved the home . Hope was amazing and checked on us. Thank you to the Blair family. "
Very Best Deluxe Ocean View...Panoramic View....First Class!!

Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2

9.6 out of 10, Exceptional, (81)
"The property was just as advertised. The CB Island Vacations team was very accommodating. We enjoyed being near the beach and especially liked the pool/recreational complex that was very near the unit. The property was perfect for a family."
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2

Beautiful house in the Upscale Maui Meadows neighborhood

10.0 out of 10, Exceptional, (6)
"amazing"
Beautiful house in the Upscale Maui Meadows neighborhood

One-of-a-Kind Maui Getaway!

10.0 out of 10, Exceptional, (108)
"The architecture and view were absolutely amazing and the house was perfect for our family. The outdoor spaces were ideal - loved the infinity pool! There were some minor issues during our stay, but the host was very attentive and quick to respond. I am confident that the owner has already handled the few remaining items. Our family is very excited to come back to this beautiful home. "
One-of-a-Kind Maui Getaway!

Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

9.8 out of 10, Exceptional, (80)
"Our family of five adults just finished a 10 day Stay here. Looks just like the pictures. The view is amazing!!!! The house is a great size for families with plenty of room to spread out and have your own space with tons of outdoor seating and areas. We enjoyed the pool and the hot tub every day and the beach is a pretty close drive. You can walk to the beach, however it is all downhill for a long way so unless you’re very fit, I wouldn’t recommend it, as you’d be going entirely uphill in the...
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4

10.0 out of 10, Exceptional, (25)
"We absolutely loved our stay at Ho’olei. Eric made sure we had everything we needed. The team takes great pride in keeping the home and grounds clean. The outdoor patio with panoramic view of the ocean and proximity to the Grand Wailea resort and beach were a highlight of our stay. The home is perfect for large family gatherings and has a fully stocked kitchen. We can’t wait to plan our next adventure back to Wailea. "
Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4

Newly Renovation, All New: Beds, Furniture, Floors, Kitchen Counters and Island

10.0 out of 10, Exceptional, (30)
"Fantastic views, luxurious interior, great location, and a fabulous host/manager. Seriously can’t ask for more. Thank you!"
Newly Renovation, All New: Beds, Furniture, Floors, Kitchen Counters and Island

Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!

9.8 out of 10, Exceptional, (139)
"We had an amazing time at this vacation rental! Right from the start, we were blown away by how clean, spacious, and well-equipped the house was. It looked just like the photos and description on VRBO. The kitchen had everything we needed to whip up our meals, and the living areas were perfect for the whole family. The deck with the hot tub was a fantastic way to unwind after a long day at the beach, and the sunset views were just incredible. We even caught some fireworks from the Grand Wailea...
Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!
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 Wailea-Makena

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (521)
"Excellent stay and wonderful place to vacation with access to the pool and the beach! Our condo was outstanding!"
Wailea Ekahi - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (700)
"Convenient location, good sized unit, clean and in good condition and walkable location."
Wailea Grand Champions - CoralTree Residence Collection

Castle Kama'ole Sands

3.0 star property
8.0 out of 10, Very good, (2219)
"Would definitely stay here again"
Castle Kama'ole Sands
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.