A coastal landscape with rocky cliffs, a body of water, and a distant mountain range under a cloudy sky.

Wailea-Makena Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Wailea-Makena vacation rentals

A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

1. Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (64 reviews)
$312 nightly
The price is $366
Oct 20 - Oct 21
Total with taxes and fees
Romantic 1 BR Condo with King Tempurpedic
A modern kitchen with a dining area, a ceiling fan, and a wall art piece.

2. Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
Wailea
10.0 out of 10, Exceptional, (39 reviews)
"Location location location! Just 1 block from the shops and Wailea beach…can’t beat that! "
United States
david k.
$358 nightly
The price is $418
Oct 28 - Oct 29
Total with taxes and fees
Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
A resort pool area with a view of the ocean and a golf course in the background.

3. Deal 245USD 11-5 thru 11-23 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's

Deal 245USD 11-5 thru 11-23 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's
Wailea
9.8 out of 10, Exceptional, (187 reviews)
"Proximity to ocean was amazing..great place to start a morning walk to Wailea Beach walk..well stalked condominium…amazing sound system..Comfortable bed and beautiful artwork..will definitely plan another visit here.."
United States
Tim T.
$482 nightly
The price is $564
Oct 17 - Oct 18
Total with taxes and fees
Deal 245USD 11-5 thru 11-23 Walk to Beach & Pool FULL AC New77" & 55"OLED TV's
A tropical garden with a waterfall, palm trees, and a variety of lush greenery.

4. 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.
Wailea Luxury Retreat | Walk to Beach & Shops
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

5. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (41 reviews)
"Absolutely loved our room. The kitchen was spacious and had all of the necessities. The best part was the lawn chairs, umbrella and tote bag provided in the room. Rooms large enough to relax and not feel so crowded."
United States
Mai
$453 nightly
The price is $537
Oct 15 - Oct 16
Total with taxes and fees
Signature Residences at Maui Banyan
A balcony with wicker furniture, a table, and a view of a golf course and buildings.

6. Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
Wailea
10.0 out of 10, Exceptional, (81 reviews)
"Great location near beach, the shops at Wailea, golf courses, restaurants, . . . .Host responded quickly and thoughtfully to any questions. The condo was clean and well stocked with beach toys like chairs, towels, . . .Very seamless move in and out. "
United States
Matthew M.
$419 nightly
The price is $491
Oct 22 - Oct 23
Total with taxes and fees
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
A kitchen with white cabinets, a marble countertop, a kettle, and a vase with flowers.

7. ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
Wailea
10.0 out of 10, Exceptional, (45 reviews)
"Great condo! "
Canada
Marcie M.
$420 nightly
The price is $490
Nov 9 - Nov 10
Total with taxes and fees
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
An outdoor patio with a grill, seating, and a view of the ocean.

8. 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, (55 reviews)
"The condo was spotless and well appointed. We hope to stay there again."
United States
Ralph N.
$474 nightly
The price is $554
Oct 16 - Oct 17
Total with taxes and fees
Ekahi 27A: Priceless Ocean View from a Private Lanai
A beach with palm trees and a clear sky.

9. Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
Wailea
10.0 out of 10, Exceptional, (165 reviews)
"Beautiful area and great location with walking distance to dining and shopping."
United States
Teri S.
$532 nightly
The price is $623
Oct 14 - Oct 15
Total with taxes and fees
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A wooden table with a bottle of wine and two glasses on a balcony overlooking a lush garden and the ocean.

10. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
Wailea
9.8 out of 10, Exceptional, (193 reviews)
"Amazing view, good size spaces nice proximity to the shops in Wailea. Overall great stay."
United States
Scott M.
$525 nightly
The price is $614
Oct 21 - Oct 22
Total with taxes and fees
#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting
A grill with a stone base, a view of the ocean, and palm trees.

11. Totally renovated, closest to the beach!

Totally renovated, closest to the beach!
Wailea
9.8 out of 10, Exceptional, (232 reviews)
"Property is beautiful, super close to beach and pools. Has everything needed for a relaxing vacation. Host was wonderful to work with."
United States
Sandy S.
$497 nightly
The price is $582
Oct 20 - Oct 21
Total with taxes and fees
Totally renovated, closest to the beach!
A pathway leading to a beach with dense green foliage on either side.

12. #239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
South Kihei
9.6 out of 10, Exceptional, (98 reviews)
"Kitchen was fully equipped. Condo was very clean and host was promt with replys. Loved our stay "
Canada
Lori D.
$479 nightly
The price is $561
Oct 21 - Oct 22
Total with taxes and fees
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
A resort with a pool, palm trees, and a view of the ocean.

13. Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!

Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!
Wailea
10.0 out of 10, Exceptional, (14 reviews)
$815 nightly
The price is $954
Oct 14 - Oct 15
Total with taxes and fees
Fabulous Condo with Amazing Ocean Views - Bldg 22! Remaining Fall $250/nt!
A balcony with a view of a golf course, a table with chairs, and a small air conditioning unit.

14. Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
Wailea
9.6 out of 10, Exceptional, (73 reviews)
"A fantastic place to stay! You can easily walk to shops, restaurants, and the golf course. Plus, the ocean view is amazing. "
United States
lily v.
$473 nightly
The price is $553
Oct 20 - Oct 21
Total with taxes and fees
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
A balcony with a view of a sunset over palm trees and a row of modern buildings.

15. Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (113 reviews)
"Great location and value!"
United States
Christopher
$301 nightly
The price is $351
Oct 23 - Oct 24
Total with taxes and fees
Beautiful, Renovated, Hale Kamaole 159
An aerial view of a coastal town with a beach, residential buildings, and a mountainous backdrop.

16. Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!

Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
South Kihei
9.2 out of 10, Wonderful, (91 reviews)
"Location was perfect. We were there right after all of the flooding and the road was damaged but did not affect our stay at all. Our host was always responsive and made sure we were comfortable! Would surely stay again.:)"
United States
Melissa P.
$360 nightly
The price is $421
Oct 14 - Oct 15
Total with taxes and fees
Experience the Magic of Maui: Your Perfect Kihei Getaway, steps from the beach!
A swimming pool with a curved design, surrounded by palm trees and a golf course.

17. 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
Wailea
10.0 out of 10, Exceptional, (62 reviews)
"Nice location and resort. Lots of clear instructions in advance from the host and inside the unit. Comfortable bed!"
United States
Richard F.
$854 nightly
The price is $1,000
Oct 20 - Oct 21
Total with taxes and fees
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
A balcony with a glass table, chairs, and a view of the ocean and palm trees.

18. 206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!

206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!
South Kihei
9.8 out of 10, Exceptional, (64 reviews)
"The Surfside is a spectacular property. You cannot go wrong. The property owner/management company was very responsive and organized."
United States
Slate S.
$469 nightly
The price is $549
Oct 16 - Oct 17
Total with taxes and fees
206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!
A beach with clear turquoise water, sandy shore, and palm trees.

19. 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, (61 reviews)
"Location is excellent."
United States
Amund N.
$558 nightly
The price is $654
Oct 14 - Oct 15
Total with taxes and fees
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
A resort with a swimming pool, palm trees, and ocean views.

20. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (993 reviews)
"Nice location. Very hospitable and Kind staff. Would stay here again"
United States
Kifaya
$303 nightly
The price is $360
Nov 12 - Nov 13
Total with taxes and fees
Aston Maui Hill
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

Days Inn by Wyndham Maui Oceanfront

Days Inn by Wyndham Maui Oceanfront

8/10 Good
"Our room was clean. The front desk staff were all very friendly and helpful. Centrally located and a good value for the price."
Michael John 4-night trip
Posted 11 hours ago
Days Inn by Wyndham Maui Oceanfront

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.

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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 $360 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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