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

Cottage in Kihei

4.98 out of 5 average rating, 219 reviews

Luxury Cottage, Saltwater Spa, Walk to Beach/Dining/Shops

Slip into a saltwater hot tub on a private deck with a cocktail and good company. The surrounding palm trees and stars above will surely add to the romantic moment. Rinse off under a warm outdoor shower, then retreat indoors to a stylish love nest. LOCATION, LOCATION, LOCATION Located in the heart of sunny South Kihei near the famous Kamaole sandy beaches. 10-minute walk to just about everything: - Kalama Beach Park (playground, tennis, volleyball, basketball, and more) - Over 23 restaurants, coffee shops, and bars - Shops, boutiques, open air markets - Farmers market and grocery store - The Cove Beach Park (paddle boarding and beginner surfing) - Kamaole Beach Park 1, 2, 3 (Kam 1 is a 20-min walk. All beaches within a 5-minute drive) Quick Drive (15-20 minutes): - Famous Makena Beach, Wailea and world class golf courses - Airport Stroll in cute little shops while trying some local shave ice. You will love Maui's most unique shopping and dining experience at Kihei Kalama Village with great places to eat and over 40 vendors and boutiques. At the south side of Kalama Beach, you will find Cove Park where you can take surfing lessons or try stand up paddle boarding. Walk beyond Cove Park and you find Charley Young beach which is part of the famous Kamaole beaches. In the morning, walk to the end of the street for coffee at Belle Surf Cafe or 5 minutes farther to the Lava Java Coffee Roasters and enjoy your coffee at the beach. During the early evening, you can relish sushi during Happy Hour at Sansei within a few minutes of the house or enjoy the gorgeous sunsets at the beach. PRIVATE OUTDOOR LIVING IN A TROPICAL SETTING - Lounging space in either deck or in a covered lanai - Weber Gas Grill - Salt water hot tub - Fully fenced tropical garden and lawn (yoga, croquet on the grass) Tropical outdoor living area for sunning, reading a book in the shade, connecting with someone close, grilling, or relaxing in the hot tub. AMENITIES - All-Clad gourmet cookware and kitchen tools - Induction range - 65-inch 4k OLED TV for the living room and 40-inch TV in the bedroom - WI-FI (high speed and easy to work from here, download 200 mb/sec, upload 20 mb/sec) - Books, games - many toiletry items provided The house includes island style furniture with a full kitchen that will delight a chef. High end cookware and kitchen tools like Henckel knives, French press, coffee grinder, a comprehensive spice rack, and a Vitamix blender. Make delicious Hawaiian smoothies from farmers market at the end of our street. 5-star luxury resort Queen mattress (Sealy Optimistic Plush Foam) with 400+ thread count pima cotton sheets and down comfortable assures a good night’s sleep. FOR THE BEACH Beach chairs, umbrellas, towels, boogie boards, coolers, ice packs, and snorkel gear provided. Lots of extras as well. We also have tennis rackets and balls for the park. Room rate includes: Hawaii Taxes (General Excise 4.166%, Accommodation: 10.25%) Private, keyless entrance to your free-standing cottage surrounded by a fenced garden paradise. Free off-street parking. Guests can call, text, or email us with any needs or questions they may have. Our housekeeper and our maintenance person live just down the street and can be at the house within 5 minutes for any urgent items. The house is right where the action is—the park, beach, restaurants, shops, and fresh market are all close by. Walk down the street to a friendly cafe for breakfast. Stroll along the shore watching carefree turtles and determined surfers. Walking around is great, but we still recommend a car. Car rental available at airport or locally in Kihei. A public bus stop is located about 5-7 minute walk from the house. Maui County approved vacation rental: Short Term Rental Permit STKM 2014 / 0001, Tax ID 085 / 245 / 5424 / 01

Jun. 24 – Jul. 1

$1,198 CAD per night
Guest favourite

Home in Kihei

4.96 out of 5 average rating, 384 reviews

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

Aug. 21 – 28

$912 CAD per night
Guest favourite

Condo in Kihei

4.91 out of 5 average rating, 132 reviews

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

Mar. 8 – 15

$586 CAD per night

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 Wailea-Makena

4.95 out of 5 average rating, 55 reviews

Luxury Condo w/wide Ocean View (Palms at Wailea)!

May 9 – 16

$745 CAD per night
Guest favourite

Condo in Kihei

4.98 out of 5 average rating, 57 reviews

Maui Retreat Ekahi 50F - All YOU Need!

Oct. 2 – 9

$741 CAD per night
Guest favourite

Condo in Wailea

4.91 out of 5 average rating, 64 reviews

Wailea Elua 1101 - Beachfront Section - Ocean View

Oct. 2 – 9

$1,281 CAD per night
Guest favourite

Condo in Kihei

5.0 out of 5 average rating, 45 reviews

Luxe 2bed Wailea, beach, ocean view, spa, golf

Dec. 5 – 12

$1,394 CAD per night
Guest favourite

Condo in Kihei

4.97 out of 5 average rating, 92 reviews

Barefoot Luxury at its Finest! WBV PHJ206

Nov. 9 – 16

$1,829 CAD per night
Guest favourite

Apartment in Kihei

5.0 out of 5 average rating, 42 reviews

Luxurious Wailea Ocean Vistas

Aug. 8 – 15

$1,312 CAD per night
Guest favourite

Home in Kihei

4.94 out of 5 average rating, 65 reviews

Hale Alana

Aug. 17 – 24

$1,895 CAD per night
Guest favourite

Condo in Wailea-Makena

5.0 out of 5 average rating, 26 reviews

Aloha Moon - The Honeymoon Hideaway

Jan. 18 – 25

$1,480 CAD per night
Superhost

Condo in Kihei

4.86 out of 5 average rating, 78 reviews

Wailea Getaway (2BD/2BTH) in Best Location!!!!!

Aug. 30 – Sep. 6

$984 CAD per night
Superhost

Home in Kihei

4.9 out of 5 average rating, 62 reviews

Whales and sunsets, front row seats every day!

Mar. 19 – 26

$1,583 CAD per night
Guest favourite

Apartment in Kihei

4.97 out of 5 average rating, 60 reviews

Wonderful Wailea Condo with Lanai Water Views

Aug. 14 – 21

$693 CAD per night
Guest favourite

Condo in Kihei

4.99 out of 5 average rating, 93 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aug. 28 – Sep. 4

$1,069 CAD per night

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