Wailea-Makena vacation rentals

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Top-rated vacation rentals in Wailea-Makena

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

Guest favorite

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

Aug 24 – 31

$650 per night
Guest favorite

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 22 – 29

$473 per night
Guest favorite

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

$300 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 favorite

Home in Kihei

4.93 out of 5 average rating, 107 reviews

Spacious one bedroom, King bed, AC/WiFi,

Sep 16 – 23

$155 per night
Guest favorite

Condo in Kihei

4.9 out of 5 average rating, 296 reviews

Everything you need to enjoy true paradise!

Nov 1 – 8

$278 per night
Guest favorite

Condo in Wailea-Makena

4.98 out of 5 average rating, 135 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

Aug 20 – 27

$425 per night
Guest favorite

Condo in Kihei

5.0 out of 5 average rating, 133 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

Feb 8 – 15

$425 per night
Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 127 reviews

Maui Dream Place at Maui Kamaole G-209, Ocean View

Dec 7 – 14

$499 per night
Superhost

Condo in Kihei

4.94 out of 5 average rating, 192 reviews

Mana Kai Maui - Beachfront Condo in Kihei

Dec 15 – 22

$550 per night
Superhost

Condo in Kihei

4.9 out of 5 average rating, 208 reviews

Gorgeous Getaway on the Beach

Aug 27 – Sep 3

$268 per night
Guest favorite

Guest suite in Kihei

5.0 out of 5 average rating, 75 reviews

Sweeping Panoramic Ocean Views - Private Ohana

Mar 11 – 18

$595 per night
Superhost

Condo in Wailea

4.88 out of 5 average rating, 16 reviews

Gorgeous Condo in Wailea Ekahi Village!

Feb 27 – Mar 6

$475 per night
Guest favorite

Condo in Wailea-Makena

4.95 out of 5 average rating, 55 reviews

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

Jul 30 – Aug 6

$474 per night
Guest favorite

Condo in Kihei

4.98 out of 5 average rating, 57 reviews

Maui Retreat Ekahi 50F - All YOU Need!

Sep 29 – Oct 6

$385 per night
Guest favorite

Condo in Kihei

4.98 out of 5 average rating, 50 reviews

PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA

Apr 30 – May 7

$549 per night

Other great vacation rentals in Wailea-Makena

Guest favorite

Condo in Wailea-Makena

5.0 out of 5 average rating, 26 reviews

Aloha Moon - The Honeymoon Hideaway

Dec 7 – 14

$803 per night
Guest favorite

Home in Kihei

4.94 out of 5 average rating, 65 reviews

Hale Alana

Dec 12 – 19

$979 per night
Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 89 reviews

Wailea Ekahi Oceanview, Beachfront King Bed Studio

Aug 23 – 30

$295 per night
Guest favorite

Apartment in Kihei

4.97 out of 5 average rating, 60 reviews

Wonderful Wailea Condo with Lanai Water Views

Aug 17 – 24

$362 per night
Guest favorite

Apartment in Kihei

5.0 out of 5 average rating, 11 reviews

Wailea Luxury Resort Vista

May 1 – 8

$699 per night
Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 93 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Nov 6 – 13

$625 per night
Guest favorite

Condo in Kihei

4.95 out of 5 average rating, 66 reviews

Ekahi 22C Toes in the Sand in Under 2 Minutes

Sep 23 – 30

$625 per night
Guest favorite

Condo in Kihei

4.95 out of 5 average rating, 42 reviews

Modern Renovated Palms at Wailea Condo!

May 27 – Jun 3

$359 per night
Superhost

Condo in Kihei

4.96 out of 5 average rating, 24 reviews

Exceptional Ocean View - King Bed - Ocean Front!

Aug 8 – 15

$766 per night
Guest favorite

Condo in Kihei

5.0 out of 5 average rating, 17 reviews

Mana Kai Palms: Oceanfront Resort ~Keawakapu Beach

Mar 9 – 16

$754 per night
Guest favorite

Home in Wailea-Makena

5.0 out of 5 average rating, 63 reviews

WOW! Stunning Ocean Views, Large Deck &Luxury Beds

May 20 – 27

$495 per night
Guest favorite

Condo in Wailea-Makena

4.93 out of 5 average rating, 83 reviews

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

Sep 7 – 14

$608 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

Your guide to Wailea-Makena

All About Wailea-Mākena

Located on the southern shore of the Hawaiian island of Maui, Wailea is a resort area famous for its white-sand beaches, sprawling golf courses, and relaxing spas. Wailea-Mākena provides a great base for visiting southern Maui’s sandy shores, such as the nearby Wailea Beach, which is just a short walk from town, or Mākena Beach, where you can go for a refreshing swim or explore the pristine coastline by paddleboard or kayak.

You can also find many interesting natural attractions nearby, such as La Perouse Bay or Ahihi-Kinau Natural Area Reserve, which is teeming with marine life. Take a break from the sun and water by visiting the Shops at Wailea, a complex that features 70 retail stores — art galleries, boutiques selling Hawaiian shirts and water-sports gear —and restaurants serving creative takes on local mahi mahi and deep-water ahi tuna.


The best time to stay in a vacation rental in Wailea-Makena

Thanks to Maui’s consistent heat all year round, this is a great place to visit at any time. During the summer, the days are long, hot, and sometimes muggy, which is why many travelers cool off in the crystal-clear water found on Maui’s beaches.

During the spring and fall, the crowds thin out, making this a great time to visit if you want to have the beaches and hiking trails all to yourself. While the clouds gather overhead more frequently in the winter and the region sees a higher amount of rain, the warm weather remains, and showers are generally quick to come and go. Winter is also the best time to visit if you’re interested in whale watching or driving along Maui’s Road to Hana, a winding road famous for its waterfall hikes and lush greenery.


Top things to do in Wailea-Makena

Mākena State Park

Mākena Beach State Park, on the south side of town, is home to one of the largest undeveloped beaches on Maui. This stretch of shoreline, commonly referred to as “Big Beach,” features glistening white sand and cerulean waters surrounded by native kiawe forests and mango groves. Wander inland and you can hike up the 360-foot-tall Pu’u Olai, a dormant volcanic cinder cone, where you can survey the coastline from on high.

Ahihi-Kinau Natural Area Reserve

Located less than a 10-minute drive from Mākena State Park, this marine reserve offers one of the area’s best snorkeling spots. The ocean floor is covered by a coastal lava field intermixed with coral, making it a popular home for many different species of tropical fish, including butterfly fish, parrotfish, surgeonfish, and turtles. At the reserve, you can snorkel directly from the shoreline.

La Perouse Bay

Just 20 minutes south of Wailea-Mākena, La Perouse Bay is outlined by lush green vegetation and jagged lava rock formations, created when the now-dormant Haleakalā Volcano last erupted in 1790. Now the blackened lava rocks shelter numerous tide pools. If you’d like to peer in at the marine creatures living there, bring shoes with thick soles, as lava rock has many sharp edges.

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Wailea-Makena?

    Four-legged friends are welcome in Wailea-Makena. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Wailea-Makena?

    Yes! Work meets play with ease at over 960 vacation rentals in Wailea-Makena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Wailea-Makena vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 1,730 vacation homes with pools in Wailea-Makena, available on Airbnb. Make a splash and soak up the sun in style!

  • Do villa rentals in Wailea-Makena have a gym?

    Absolutely! We offer over 50 villa rentals with a gym in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in condo rentals in Wailea-Makena?

    Experience the best of Wailea-Makena with our condo rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do townhouse rentals in Wailea-Makena have wireless internet?

    Absolutely! We offer over 20 townhouse rentals with wireless internet in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly condo rentals in Wailea-Makena?

    Wailea-Makena has more than 810 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Wailea-Makena have a bbq area?

    Absolutely! We offer over 40 apartment rentals with a bbq area in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wailea-Makena have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Hotel Rentals in Wailea-Makena?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 20 homes with a gym, over 30 homes with wireless internet, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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