
House vacation rentals in Wailea
Find and book unique houses on Airbnb
Quick stats about house rentals in Wailea

Total vacation rentals
Explore 60 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

Verified guest reviews
Over 2,030 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Wailea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in Wailea
Guests agree: these houses are highly rated for location, cleanliness, and more.

Enjoy paradise living at the THERE Maui House!
Permit #STKM 2018/0006 Located on the south side of Maui in a quiet neighborhood close to the beach & the best shave ice, this cozy, two bedroom house with newly added split AC system awaits! Whether you decide to dance to Don Ho on vinyl, try a new recipe, or play the ukulele, this space was thoughtfully designed to inspire you to be THERE & enjoy your time in paradise! For more pictures & tips, check out the THERE Maui House on our blog at there maui dot com and on IG at @livetravelbe.there

3B2B w/HotTub FamilyComfort HawaiianaCharm Central
True Hawaiiana charm, comfort, and convenience for your family vacation. Located in the heart of Maui, in historic Wailuku town, with easy access to all parts of the island for all your planned activities. Beaches within 10 minutes drive time in 3 directions and the beautiful West Maui mountains w/ Iao Valley National park behind. After a day of adventure come home to a restful time in the HOT TUB under the bright stars . Walk to boutiquey stores ,Coffee shops, First Friday party w/the locals

Beautiful Beachfront Townhouse !
OUR MAUI BEACH HOUSE... This is the perfect place for a family vacation and retreat!! And it is right on the beach! Many of our guests enjoy staying right on our property or on our beach -- no need to leave. A very large two bedroom, three bath - solar powered redwood townhouse we built in 1977 as a family retreat, with a fully-equipped kitchen and laundry. This is a comfortable beach house and we have done remodeling, refurnishing and updating. The master bedroom has huge ocean views.

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01
WONDERFUL! Three bedroom hale (home) in the Central Kihei area of Maui. Wood floors, lots of space, kitchen fully stocked, BBQ and so much more. Great for kids, elderly, and young at heart. This house is your home away from home. We have all of the necessary items for a home. If we do not have something please let us know and we will try our best to accommodated. Walking distance to the beach, shopping, park, public transportation, etc... You will not find a better place in Kihei.

The Blue Door on Church Street | Vintage One Bedro
Stay in a restored 1929 plantation-style retreat at The Blue Door on Church Street in historic Wailuku. This private one-bedroom space features a king Helix bed, queen memory foam sleeper sofa, high ceilings, original wood details, kitchenette, rainfall shower, soaking tub, AC, fast WiFi, Smart TV, parking, and access to a shared infrared sauna. Walk to cafés, restaurants, shops, yoga, and the ʻĪao Theater, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui adventures.

NEW! 1 bed | Walk to town/beach (S. Kihei)
BEAUTIFUL 1BED + SOFA BED NEWLY REMODELED Clean, safe, fully equipped, comfortable home. Located in central Kihei just two blocks from the beach, this modern beach pad was designed with an eye toward comfort and entertainment. A/C in all rooms. *5 minutes drive to Starbucks, golf, gyms, beach, parks, dining, entertainment, supermarkets, and shopping! The property is secured and fully fenced. The common area consists of a driveway, garden and 2 outdoor showers.

12 Minute Walk Kamaole Beach II-Quiet Private Easy
This 1 bedroom/1 bath suite is a self contained, attached ohana (ADU) with private entry. Off street parking is 10 seconds from your door. Located a 12 minute walk straight down to Kamaole Beach II. Convenient Location, Quiet and Private. I am a SUPERHOST, see the 4.97 reviews and comments. INSTANT BOOK for a great stay. All fees and taxes are listed & collected when you book. There are no surprise or additional costs. Permit #BBKM 2O19/OOO2

Modern Family Kihei Home by the Beach
Aloha! Welcome to one of the best located homes on the island! Located just under half a mile (or 5 minute walk) from the beach, surfing, park, restaurants, shops and stores. Our modern property offers complete relaxation for the perfect Maui vacation. Our home offers kid friendly amenities, A/C in ALL ROOMS, an espresso machine and Vitamix. Our calendar is always up to date. Please inquire with any questions, we will respond within 1 hour!

Stunning ocean view Villa, Heated pool, Wailea
Legendary Maui sunsets from your private lanai. Whales splashing offshore in season. A heated pool all your own, tucked into over half an acre of tropical gardens. This artist-designed Victorian-style villa is 5 minutes from Keawakapu Beach and the Shops at Wailea, and made for families, with shallow-end pool steps, a gated lanai, and baby gear ready on arrival. Boutique hotel attention, complete privacy. Your view retreat awaits.

Ho'olei #93-2-Beautifully Appointed-Well Equipped
Book with confidence this luxurious 3 bedroom, 3.5 bathroom (2426 sq. ft) villa that provides everything that you need to have a great vacation. The house offers tremendous value with it's amenities, location, and level of finishes. PMI Maui manages many units in South Maui. Please let us know if you are interested in any of our units and we will send you the Airbnb link to view all of our listings and reviews.

4BR Kihei Retreat Walk to Beach A/C Family Ready
We are Experienced Hosts through other channels. See some of the GREAT 5 STAR reviews in the Property description. BOOK NOW AND ENJOY A 5 STAR HOME Our South Maui rental home accommodates up to eight guests, a comfortable space for your Tropical Hawaiian vacation. Four bedrooms and 2,400 square ft of living space and the beautiful outdoor living room to enjoy and relax after a day of sightseeing

South Maui Guesthouse
This air conditioned very exclusive, private 2-bedroom Guest House is surrounded with lush gardens on a ½ acre property, off the street located in an upscale very private neighborhood (Maui Meadows, above Wailea), yet minutes from the best beaches Maui has to offer. A real Hawaiiian retreat, where you wake up to the sound of birds, not traffic. Permit Number BBKM2018/xxx3 GETxxxxxxxx2801
Popular amenities for Wailea house rentals
House rentals with a pool

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

Stunning One Bd Partial ocean, AC, wifi,Pool C209

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

Kihei 533- OceanView, 5 min drive to stores/food

South Maui • Pool • Hot Tubs• Beach • Ocean View

Maalaea Kai 307 - Maui Prime Oceanfront

Centrally located and steps to the beach!

Kihei Ground Floor: AC, Steps to Pool & Beach
Weekly house rentals

Kahili Suite - Historic charm meets Luxury

Vineyard Village Maui Ohana 2BR/1 Bathroom

Spacious one bedroom, King bed, AC/WiFi,

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC

Kihei's Family Home Tropical Paradise BBQ, Hot Tub

Bungalow w pickleball/tennis steps from beach

Cottage Keawakapu Beach

A201a-The closest Maui Banyan studio to the beach
Private house rentals

Maui Kamaole J214 Budget Luxury in a 2brm/2bath Ex

Nahenahe Cottage -Maui Meadows

Unobstructed Oceanfront View | Turtles and Whales!

exquisite condo in KKN #174

1Bedroom Condo, Steps from Kamaole Beach/Kihei, HI

Central 3 bed 1 bath Cottage

Brand New 2 Bed/ 1Bath Cottage

The Blue Door on Church Street | Spacious Two Bedr
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,976 | ﺩ.ﺇ 2,159 | ﺩ.ﺇ 1,877 | ﺩ.ﺇ 1,972 | ﺩ.ﺇ 1,774 | ﺩ.ﺇ 1,818 | ﺩ.ﺇ 1,818 | ﺩ.ﺇ 1,473 | ﺩ.ﺇ 1,476 | ﺩ.ﺇ 1,634 | ﺩ.ﺇ 1,634 | ﺩ.ﺇ 1,818 |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°C |
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- Maui
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