
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.

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.

Stunning One Bd Partial ocean, AC, wifi,Pool C209
C209 is a gorgeous 1 bedroom, 1 bathroom condo with a/c. There is a king size bed in the bedroom. The bathroom has a shower. It is the perfect combination of Hawaiian calmness and modern amenities. The living room combines a tropical decor with new electronics. The kitchen has state of the art new appliances and the island gives lots of room for preparing meals. Lovely pool area with hot tub, saunas & 5 bbq grills. Tennis & pickleball courts. FREE parking. NO elevators, stairs only

Cute Cottage-Large Outdoor Deck
Permit #STKM 2018/0006 Located on the south side of Maui in a quiet neighborhood close to the beach & the best shave ice, this intimate, one bedroom cottage with split AC system awaits! Whether you decide to dance to vintage vinyl, try a new recipe, or play the ukulele, this stylish indoor and outdoor space was thoughtfully designed to inspire you to be THERE & enjoy your time in paradise! For more pictures & tips, check out our blog at there maui dot com and our IG at @livetravelbe.there

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.

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

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

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

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

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

A201a-The closest Maui Banyan studio to the beach

Kamaole Sands 3104-Bright, Clean, and Fresh!
Weekly house rentals

Kahili Suite - Historic charm meets Luxury

exquisite condo in KKN #174

3 Bedroom Private House Kihei /Wailea Maui

Nahenahe Cottage - Maui Meadows

Vineyard Village Maui Ohana 2BR/1 Bathroom

Oceanfront Koa Lagoon Condo w/ Sunset Views

Keawakapu Beach Cottage

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC
Private house rentals

Oceanview Penthouse • Modern • 2 Min Walk to Beach

The Blue Door on Church Street | Spacious Two Bedr

Chic Villa 2 | Modern Vibes by the Ocean

Ocean Front Cottage, 30 steps to the beach!

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

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

1 Bedroom Villa with Ocean Views, Steps to Beach

Central 3 bed 1 bath Cottage
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
- Kaanapali Beach
- Lahaina Beach
- Wailea Beach
- Polo Beach
- Honolua Bay
- Kapalua Bay Beach
- Maui Vista Condominium
- Big Beach
- Black Rock Beach
- Black Sand Beach
- Haleakala National Park
- Kihei Kai Nani
- Kamaole Beach Park II
- Maui Ocean Center
- Hāmoa Beach
- Maui Arts & Cultural Center
- PacWhale Eco-Adventures
- Aston Mahana at Kaanapali
- Peahi
- Kahana Beach
- Maui Tropical Plantation
- Kamaole Beach Park III
- Nakalele Blowhole
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