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Wailea, HI Condos and Holiday Rentals
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Wailea Beach
Little Beach
Makena Beach
Keawakapu Beach
Ulua Beach
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351 rentals
in Wailea.
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
61
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
25
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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5 Star Reviews! Wailea Ekolu with Ocean Views & Great Location!
26
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!
32
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Fall 2024 Remodel! Brand New Luxury! Unbelievable Ocean View! Sleeps 5!
4
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Wailea Ekahi 36E! One of the best locations in Wailea.
19
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Luxury Wailea Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.
25
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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Wailea Ekolu #105 Partial Ocean view, Sleeps 4
22
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Wailea Ekahi #25-C Near Keawakapu Beach, Garden View, A/C, Pool Access
17
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Stunning Ocean View Wailea Beach Villa- Book & Save
16
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 9
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Ocean View, Close to Beach&Pool Sleeps 10
20
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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Great for families and couples. Next to a tropical pool in Hawaiian landscape.
27
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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�Georgeous 5-STAR Wailea Retreat!Tranquil Corner unit, Top tier Upgrades�
57
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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Wailea Elua 102 Remodeled, Central A/C, Full Ocean View, Near Ulua Beach
19
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Palms at Wailea 303 will be your new favorite! Clean & beautifully remodeled
29
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Ocean View, Steps away from the pool
7
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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Top Floor One Bedroom at Wailea Ekolu 208
21
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Just Steps to Kamaole III Beach!!!
30
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach
21
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Incredible Ocean Views! Premier Building at Makena Surf B305
10
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Get Spoiled in deluxe unit-Kihei Kai Nani /best location!/Jan.18-23, Feb.21-26
17
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 5
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Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill
21
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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Direct Ocean Front Polo Beach 805!
10
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Beautifully decorated! Very private! Partial Ocean View! Palms at Wailea 2202
45
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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2 bedroom, 2 bath family friendly Grand Champions 130!
10
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4
12
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Wailea Townhome, Perfect for Families! Wailea Ekahi 25B
3
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 7
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New! Luxurious 3bd Villa at Wailea Beach Villas unit E201
6
Condo/Apartment
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3 bedrooms
4 bathrooms
Sleeps 8
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Palms at Wailea #1903 Luxe Remodel, Ground Floor, Walk to Beach and Shops!
23
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms
10
Condo/Apartment
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4 bedrooms
3 bathrooms
Sleeps 8
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Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wifi
17
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
15
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 10
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WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!
9
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai
20
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
27
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 2
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Lush Tropical Views! GC 136
7
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach
19
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Kihei Surfside #609: Oceanfront Gem with Stunning Views and Comfort
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Incredibly Large Polynesian Style Villa in Wailea
21
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 6
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Private and Sweet Wailea 1 BD+2 BA Grand Champions Villa
19
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING
17
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3
14
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 8
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Wailea Ekahi6D NEWLY UPDATED 2nd Floor, Part Ocean View,1 min walk to Beach&Pool
21
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Listen to the birds chirp!
20
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4
8
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!
15
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Direct ocean front, Polo Beach Club 705!
7
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Stunning unit! Beautiful Remodel! Ocean Views! Ekahi 5E
9
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 3
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Beachfront, Polo Beach Wailea/Makena #103, Ground Floor
7
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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Panoramic Ocean Views! - * Luxury Villa! * - 3 Bed/3 Bath - Owner Direct Savings
18
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Showing results 1-50 of 351
Frequently Asked Questions about Wailea
Do any holiday rentals in Wailea have a pool?
Yes, here are some popular holiday rentals in Wailea that have a pool:
Beaut Secluded Resort in Renowned Gently Sloping Hills & Verdant Norfolk Pines
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
See all holiday rentals with a pool in Wailea on Tripadvisor
Do any holiday rentals in Wailea have internet access?
Yes, here are some popular holiday rentals in Wailea that have internet access:
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
5 Star Reviews! Wailea Ekolu with Ocean Views & Great Location!
See all holiday rentals in Wailea on Tripadvisor
What are the best pet friendly rentals in Wailea?
The best pet friendly rentals in Wailea are:
Experience the Magic of Maui at Ekahi 13C
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
See all pet friendly holiday rentals in Wailea on Tripadvisor
What are some great rentals in Wailea that are kid friendly?
Some of the most popular kid friendly rentals in Wailea are:
Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
5 Star Reviews! Wailea Ekolu with Ocean Views & Great Location!
See all kid friendly holiday rentals in Wailea on Tripadvisor
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