
Condo holiday rentals in Wailea
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Top-rated condo rentals in Wailea
Guests agree: These condos are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Wailea condo rentals
Weekly condo rentals

Oceanfront Getaway, Brand New, Steps To Beach

Spectacular Ocean Front 1bd at Menehune Shores

Wailea Elua 1101 - Beachfront Section - Ocean View

Gorgeous Condo in Wailea Ekahi Village!

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

Sugar Beach Resort Beach / Ocean Front Unit 426

Modern Renovated Palms at Wailea Condo!

Aloha Moon - The Honeymoon Hideaway
Pet-friendly condo rentals

Amazing Oceanfront Apartment

Westin Kaanapali Ocean Resort Villas North Studio

Maui Tropical Sunset - First Floor with The Extras

Beautiful Views~

High-Floor Island Surf | AC | Walk to Beach

Maui Banyan Resort 2 Beds- Beach, Pool, AC, Wifi

A jewel on Oceanfront & Breath Taking Views.

Breathtaking Location-Sugar Beach #129
Condo rentals with a pool

Gem near Keawakapu Beach - Privacy and Ocean Views

Stunning Wailea 2/2, AC, Upper Fl , walk to beach

Beautiful Ocean Views and Aloha at Wailea Ekolu!

Maui Retreat Ekahi 50F -All YOU Need!

Mana Kai Palms: Beachfront Resort ~Keawakapu Beach

Wailea Ekolu Village | 912

Wailea Hidden Gem

Wailea Ekolu Ocean Suite 207 AC and Ocean Views
Quick stats about condo rentals in Wailea
Total rentals
1.3K properties
Nightly prices starting at
$15Â AUD before taxes and fees
Total number of reviews
40K reviews
Family-friendly rentals
780 properties are a good fit for families
Rentals with a pool
1.3K properties have a pool
Rentals with dedicated workspaces
760 properties have a dedicated workspace
Destinations to explore
- Family-friendly rentals Wailea
- Pet-friendly rentals Wailea
- Fitness-friendly rentals Wailea
- Rentals with beach access Wailea
- Rentals with outdoor seating Wailea
- Rentals with a patio Wailea
- Townhouse rentals Wailea
- Waterfront rentals Wailea
- Rentals with a kayak Wailea
- Beach condo rentals Wailea
- House rentals Wailea
- Rentals with an EV charger Wailea
- Villa rentals Wailea
- Serviced apartment rentals Wailea
- Beachfront rentals Wailea
- Rentals with a hot tub Wailea
- Cottage rentals Wailea
- Rentals with a washing machine and dryer Wailea
- Rentals with a sauna Wailea
- Apartment rentals Wailea
- Hotel rentals Wailea
- Rentals with pools Wailea
- Luxury rentals Wailea
- Condo rentals Wailea
- Condo rentals Maui County
- Condo rentals Hawaii
- Condo rentals United States
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Honolua Bay
- Kapalua Bay Beach
- Spreckelsville Beach
- Olowalu Beach
- Pahoa Beach
- Manele Golf Course
- HÄmoa Beach
- Maui Ocean Center
- Kaipukaihina
- Wailea Beach
- Oneloa Beach
- Puu Olai Beach
- Changs Beach
- Palauea Beach
- Old Lahaina Luau
- Maui Golf & Sports Park
- Wailau Valley
- Wailea Golf Club
- Ka'anapali Golf Courses