Holiday rentals in Wailea-Makena

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Top-rated holiday rentals in Wailea-Makena

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

Guest favourite
Cottage in Kihei
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
19–26 JulIndividual Host,
£693 per night
4.98 out of 5 average rating, 220 reviews
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
4–11 SeptIndividual Host,
£527 per night
4.96 out of 5 average rating, 382 reviews
Guest favourite
Apartment 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!
16–23 OctIndividual Host,
£432 per night
4.98 out of 5 average rating, 58 reviews

Popular amenities for Wailea-Makena holiday 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 holiday rentals in Wailea-Makena

Guest favourite
Flat in Kihei
Wonderful Wailea Condo with Lanai Water Views
3–10 JanProfessional Host,
£394 per night
4.97 out of 5 average rating, 60 reviews
Guest favourite
Apartment in Wailea-Makena
Tiki Tiki - A Gorgeous Boho Beach Hideaway!
18–25 May
£456 per night
5.0 out of 5 average rating, 24 reviews
Guest favourite
Apartment in Kihei
Luxe 2bed Wailea, beach, ocean view, spa, golf
2–9 DecIndividual Host,
£733 per night
5.0 out of 5 average rating, 45 reviews
Guest favourite
Apartment in Wailea-Makena
Luxury Condo w/wide Ocean View (Palms at Wailea)!
10–17 Dec
£628 per night
4.95 out of 5 average rating, 55 reviews
Guest favourite
Apartment in Wailea
Wailea Elua 1101 - Beachfront Section - Ocean View
7–14 DecProfessional Host,
£741 per night
4.9 out of 5 average rating, 63 reviews
Guest favourite
Apartment in Kihei
Mana Kai Palms: Oceanfront Resort ~Keawakapu Beach
25 Oct – 1 NovProfessional Host,
£680 per night
5.0 out of 5 average rating, 16 reviews
Guest favourite
Apartment in Kihei
Barefoot Luxury at its Finest! WBV PHJ206
2–9 SeptProfessional Host,
£1,057 per night
4.97 out of 5 average rating, 92 reviews
Guest favourite
Apartment in Wailea-Makena
Maui Wailea Brand New Modern Spacious Condo
5–12 Aug
£294 per night
5.0 out of 5 average rating, 38 reviews
Guest favourite
Apartment in Wailea-Makena
Wailea Surf Shack: Golf, shopping & beaches!
3–10 Sept
£393 per night
5.0 out of 5 average rating, 30 reviews
Guest favourite
Flat in Kihei
Wailea Luxury Resort Vista
11–18 JulIndividual Host,
£759 per night
5.0 out of 5 average rating, 11 reviews
Guest favourite
Apartment in Kihei
Modern Renovated Palms at Wailea Condo!
5–12 JunProfessional Host,
£408 per night
4.95 out of 5 average rating, 40 reviews
Superhost
Apartment in Kihei
Exceptional Ocean View - King Bed - Ocean Front!
16–23 JunProfessional Host,
£793 per night
4.96 out of 5 average rating, 24 reviews

Quick stats about holiday 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