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Wailea-Makena Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Wailea-Makena vacation rentals

Outdoor pool, open 8:00 AM to 9:30 PM, sun loungers

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (921 reviews)
"Unit was spacious with great ocean view."
United States
DARSHAN
$345 nightly
The price is $409
Jul 9 - Jul 10
Total with taxes and fees
Aston Maui Hill
Exterior

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (27 reviews)
"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"
United States
Julie
$430 nightly
The price is $510
Jun 13 - Jun 14
Total with taxes and fees
Signature Residences at Maui Banyan
2 bedrooms, desk, iron/ironing board, WiFi

Oceanfront Condo at the Mana Kai Maui, Luxurious, Designer Remodeled

Oceanfront Condo at the Mana Kai Maui, Luxurious, Designer Remodeled
South Kihei
9.6 out of 10, Exceptional, (67 reviews)
"Everything was as advertised and the place was great! "
United States
Pratik P.
$956 nightly
The price is $1,023
Jun 14 - Jun 15
Total with taxes and fees
Oceanfront Condo at the Mana Kai Maui, Luxurious, Designer Remodeled
Beach nearby, sun loungers, beach towels

Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades

Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades
Wailea
10.0 out of 10, Exceptional, (162 reviews)
"The unit is big and comfortable, very clean, the access code setup works well (no keys), and the host was very accommodating ."
United States
pia
$474 nightly
The price is $555
Jun 13 - Jun 14
Total with taxes and fees
Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades
Interior

Ocean View Large Lanai Kamaole Sands

Ocean View Large Lanai Kamaole Sands
South Kihei
10.0 out of 10, Exceptional, (2 reviews)
"The condo was well kept and had everything we needed! The location was phenomenal. The host was very responsive!"
United States
Valerie S.
$463 nightly
The price is $498
Jun 13 - Jun 14
Total with taxes and fees
Ocean View Large Lanai Kamaole Sands
Interior

180 Degree Ocean View in Wailea! WE204

180 Degree Ocean View in Wailea! WE204
Wailea
10.0 out of 10, Exceptional, (3 reviews)
"The location and view were fabulous. Walking distance to many restaurants and shops."
United States
Carolyn C.
$594 nightly
The price is $694
Jun 21 - Jun 22
Total with taxes and fees
180 Degree Ocean View in Wailea! WE204
Dining

Stunning Property in Building 10 of Kamaole Sands

Stunning Property in Building 10 of Kamaole Sands
South Kihei
10.0 out of 10, Exceptional, (68 reviews)
"Excellent location across great beaches in a walkable location...sunsets from the lanai were great !"
United States
STEPHEN C.
$799 nightly
The price is $934
Jun 14 - Jun 15
Total with taxes and fees
Stunning Property in Building 10 of Kamaole Sands
On the beach, sun loungers, beach towels

Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
Wailea
10.0 out of 10, Exceptional, (58 reviews)
"Cozy place, well stocked kitchen, beautiful beach walks! "
United States
M. A. B.
$554 nightly
The price is $649
Jun 13 - Jun 14
Total with taxes and fees
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
Outdoor dining

Ekahi 27A: Priceless Ocean View from a Private Lanai

Ekahi 27A: Priceless Ocean View from a Private Lanai
Wailea
9.8 out of 10, Exceptional, (49 reviews)
"The condo was spotless and well appointed. We hope to stay there again."
United States
Ralph N.
$627 nightly
The price is $733
Jun 13 - Jun 14
Total with taxes and fees
Ekahi 27A: Priceless Ocean View from a Private Lanai
TV

Steps to Kamaole 3 Beach

Steps to Kamaole 3 Beach
South Kihei
9.2 out of 10, Wonderful, (30 reviews)
"We had an amazing time! The condo was perfect for our group. We can’t wait to come back!"
United States
Teri M.
$475 nightly
The price is $511
Jun 13 - Jun 14
Total with taxes and fees
Steps to Kamaole 3 Beach
Pool

Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (60 reviews)
"It was a very short stay for us so we didn't get a chance to utilize the many amenities but Ralph was extremely accommodating and fantastic with communication!"
United States
Matt O.
$359 nightly
The price is $420
Jun 19 - Jun 20
Total with taxes and fees
Romantic 1 BR Condo with King Tempurpedic
Property grounds

Wailea Luxury Retreat | Walk to Beach & Shops

Wailea Luxury Retreat | Walk to Beach & Shops
Wailea
9.4 out of 10, Exceptional, (8 reviews)
"Excellent communication and the facilities were really nice with Two pools to choose from! Close to shops and walking paths "
United States
Jennifer A.
$559 nightly
The price is $671
Jun 14 - Jun 15
Total with taxes and fees
Wailea Luxury Retreat | Walk to Beach & Shops
Outdoor dining

Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well

Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
South Kihei
10.0 out of 10, Exceptional, (169 reviews)
"Great place to stay, close to beaches, and shops."
United States
Anonymous traveler
$329 nightly
The price is $385
Jun 13 - Jun 14
Total with taxes and fees
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
Pool

206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!

206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!
South Kihei
9.8 out of 10, Exceptional, (59 reviews)
"We had an amazing stay at this property. Booking was seamless, with prompt and clear communication from the host. Check-in was easy. Ample parking. The suite had everything needed for a comfortable stay. The grounds are lovely, and the view is incredible! We really liked staying oceanside of S Kihei road and steps away from the beach. I would have no hesitation booking this property again."
Canada
Kara G.
$496 nightly
The price is $580
Jun 15 - Jun 16
Total with taxes and fees
206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!
Exterior

Newly Remodeled Directly Across the Street from Kamaole 3 Beach

Newly Remodeled Directly Across the Street from Kamaole 3 Beach
South Kihei
10.0 out of 10, Exceptional, (26 reviews)
"Clean, comfortable, great location! "
United States
Kiana O.
$631 nightly
The price is $682
Jul 8 - Jul 9
Total with taxes and fees
Newly Remodeled Directly Across the Street from Kamaole 3 Beach
Smart TV, DVD player, stereo

101 - 2 bed/2 bath with A/C! Ground Floor Oceanfront with Breathtaking Views!

101 - 2 bed/2 bath with A/C! Ground Floor Oceanfront with Breathtaking Views!
South Kihei
10.0 out of 10, Exceptional, (52 reviews)
"This unit was perfect for my 2 week stay. It was clean, close to beach, nicely stocked kitchen, couldn’t have been any better. I highly recommend it for your Maui stay."
United States
Karen S.
$952 nightly
The price is $1,113
Jun 27 - Jun 28
Total with taxes and fees
101 - 2 bed/2 bath with A/C! Ground Floor Oceanfront with Breathtaking Views!
Beach nearby

Across from Kamaole 2 Beach, concrete building, well maintained.

Across from Kamaole 2 Beach, concrete building, well maintained.
South Kihei
10.0 out of 10, Exceptional, (164 reviews)
"Great host, location, and property. We really enjoyed our stay. The property was very quiet and relaxing. Hope to stay here again on future trips."
United States
Andrew W.
$329 nightly
The price is $385
Jun 13 - Jun 14
Total with taxes and fees
Across from Kamaole 2 Beach, concrete building, well maintained.
Beach nearby, sun loungers, beach towels

Oceanview, Sleeps 8, Gourmet Kitchen,@Kam 2, Pools/HotTubs,Tennis,5 Star Reviews

Oceanview, Sleeps 8, Gourmet Kitchen,@Kam 2, Pools/HotTubs,Tennis,5 Star Reviews
South Kihei
9.6 out of 10, Exceptional, (67 reviews)
"Our weeklong stay at this property was outstanding! The host was great to communicate arrival and check-out instructions. The apartment accommodated our family of seven very comfortably (with the sofa bed). It had great beach access and many restaurant and shopping options within walking distance. We enjoyed the beach chairs, boogie boards, and other beach toys available on the patio. The host has a nice kitchen and a washer/dryer set for eating in and doing laundry as needed. I would highly...
United States
Russell W.
$720 nightly
The price is $843
Jun 13 - Jun 14
Total with taxes and fees
Oceanview, Sleeps 8, Gourmet Kitchen,@Kam 2, Pools/HotTubs,Tennis,5 Star Reviews
1 bedroom, desk, free WiFi, bed sheets

Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!

Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!
South Kihei
9.2 out of 10, Wonderful, (19 reviews)
"The location of this unit is wonderful. Close to beach, parks, restaurants, and tennis. "
United States
Paul B.
$524 nightly
The price is $613
Jun 13 - Jun 14
Total with taxes and fees
Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!
Outdoor pool

Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access

Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access
Wailea
10.0 out of 10, Exceptional, (20 reviews)
"Fabulous unit! Clean, supplied with everything you will need and sharp knives! Simone was so lovely to work with! "
United States
Cathryn H.
$1,050 nightly
The price is $1,228
Jun 13 - Jun 14
Total with taxes and fees
Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access
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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Top Wailea-Makena Hotel Reviews

Castle Kama'ole Sands

Castle Kama'ole Sands

10/10 Excellent
"Staff very friendly. Room was clean and spacious. Very close to a beach."
Charlene 6-night trip
Posted 1 hour ago
Castle Kama'ole Sands

Find out more about Wailea-Makena

Everything you need to know about Wailea-Makena vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wailea-Makena vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wailea-Makena vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wailea-Makena vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wailea-Makena. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wailea-Makena in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $409 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wailea-Makena rentals

At Expedia, we put the best Wailea-Makena vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wailea-Makena rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wailea-Makena vacation.

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