Vacation rentals in Wailea-Makena

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Top-rated vacation rentals in Wailea-Makena

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Kihei
Stunning ocean view, heated pool at home by Wailea
Last minute bookings 5 days before arrival, and week long stays are 10% off. Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003
Sep. 4 – 11
$909 CAD per night
4.96 out of 5 average rating, 382 reviews
Guest favourite
Condo in Kihei
160KReno-Stunning Palms in Wailea Condo-Beach/Golf
Brand New 160K Renovation+Redecoration for a Hawaiian Beach Vibe.Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa.World Class Golf+Shopping.Ground floor condo with private lanai that overlooks the grass.King Master Bed with a private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel/take long tropical beach walk.BOOKINGS UP TO 365 DAY
Dec. 9 – 16
$628 CAD per night
4.91 out of 5 average rating, 131 reviews
Guest favourite
Condo in Kihei
Maui Retreat Ekahi 50F - All YOU Need!
Just bring yourself, everything else is HERE! Towels, beach chairs, umbrella, boogie board, whatever you need!!!Beautiful 2nd floor unit has an open, garden/ mountain view. The vaulted ceilings give that open air feeling. Tastefully decorated not overdone, 50F makes you feel at home from the moment you walk in. The NEW (3/23) sofa pulls out to a queen size sleeper in the living room. Zoom call if you are “flexcationing”. The BRAND NEW Fitness Roojust opened up at the pavilion in February 2024!
Aug. 17 – 24
$765 CAD per night
4.98 out of 5 average rating, 56 reviews

Popular amenities for Wailea-Makena vacation rentals

Stay near Wailea-Makena's top sights

Kamaole Beach Park II201 locals recommend
The Shops at Wailea222 locals recommend
Makena Beach149 locals recommend
Kamaole Sands3 locals recommend
Fairmont Kea Lani - Maui5 locals recommend
Andaz Maui At Wailea Resort - A Concept By Hyatt17 locals recommend

Other great vacation rentals in Wailea-Makena

Guest favourite
Condo in Kihei
Barefoot Luxury at its Finest! WBV PHJ206
Sep. 2 – 9
$1,822 CAD per night
4.97 out of 5 average rating, 92 reviews
Guest favourite
Condo in Kihei
Mana Kai Palms: Oceanfront Resort ~Keawakapu Beach
Oct. 25 – Nov. 1
$1,171 CAD per night
5.0 out of 5 average rating, 16 reviews
Guest favourite
Condo in Kihei
Ekahi 22C Toes in the Sand in Under 2 Minutes
Sep. 4 – 11
$1,188 CAD per night
4.95 out of 5 average rating, 66 reviews
Superhost
Condo in Kihei
Exceptional Ocean View - King Bed - Ocean Front!
Jun. 16 – 23
$1,367 CAD per night
4.96 out of 5 average rating, 24 reviews
Guest favourite
Apartment in Kihei
Wonderful Wailea Condo with Lanai Water Views
Aug. 10 – 17
$691 CAD per night
4.97 out of 5 average rating, 58 reviews
Guest favourite
Condo in Wailea-Makena
Wailea Surf Shack: Golf, shopping & beaches!
May 8 – 15
$677 CAD per night
5.0 out of 5 average rating, 30 reviews
Guest favourite
Condo in Wailea-Makena
Maui Wailea Brand New Modern Spacious Condo
Aug. 5 – 12
$506 CAD per night
5.0 out of 5 average rating, 38 reviews
Superhost
Condo in Kihei
Wailea Getaway (2BD/2BTH) in Best Location!!!!!
May 15 – 22
$1,044 CAD per night
4.86 out of 5 average rating, 78 reviews
Superhost
Home in Kihei
Whales and sunsets, front row seats every day!
Oct. 26 – Nov. 2
$1,424 CAD per night
4.9 out of 5 average rating, 61 reviews
Guest favourite
Condo in Wailea-Makena
Tiki Tiki - A Gorgeous Boho Beach Hideaway!
May 22 – 29
$786 CAD per night
5.0 out of 5 average rating, 24 reviews
Guest favourite
Condo in Kihei
Oceanfront Mana Kai Penthouse..Heaven meets Earth!
Sep. 1 – 8
$1,140 CAD per night
4.99 out of 5 average rating, 92 reviews
Superhost
Condo in Kihei
Luxury Wailea Remodel - Beachfront Community
Sep. 14 – 21
$568 CAD per night
4.78 out of 5 average rating, 67 reviews

Quick stats about vacation rentals in Wailea-Makena

Total rentals

1.9K properties

Rentals with dedicated workspaces

960 properties have a dedicated workspace

Rentals with a pool

1.7K properties have a pool

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

41K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Hawaii
  4. Maui County
  5. Wailea-Makena