
House vacation rentals in Wailea
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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.

The Blue Door on Church Street | Spacious Two Bedr
Enjoy Haleakalā views from this spacious two-bedroom upstairs retreat at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Features include a king Helix bed, queen Helix bed, full-size memory foam sleeper sofa, full kitchen, rainfall shower, AC, fast WiFi, Smart TV, parking for two vehicles, and a large private deck with outdoor dining and lounge seating. Walk to local cafés and restaurants, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui attractions

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.

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.

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. Not a condo with condo noise. 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.

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

Condo in Kihei 2 BR - 2 bath Condo
Maui is a magical place, where the sun, and sand can relax and rejuvenate you. We offer a lovely 2 bed and 2 bath unit with beautiful ocean views. We are directly across the street from Kama'ole III Beach Park. This beach is great for families! Transient Accommodation Tax Number: TA-025-135-1040-01R

Oceanview Home with Private pool and hot tub
Come stay with me here in sunny south Maui at this beautiful, lovingly remodeled ocean view home with private pool. There are amazing ocean views from almost all rooms in the house and the wrap around covered deck is perfect for indoor/outdoor style island living. STRH Permit # STKM 2013/0004
Popular amenities for Wailea house rentals
House rentals with a pool

Aloha Aku Bamboo Suite – Discover Beachfront Seren

Centrally located and steps to the beach!

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

Oceanfront Stunner w/ Cruiser Bikes & Pickleball

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

Maalaea Kai 307 - Maui Prime Oceanfront

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

Stunning One Bd Partial ocean, AC, wifi,Pool C209
Weekly house rentals

204 Punahoa Oceanfront studio With A/C!

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

Kamaole Sands 3104-Bright, Clean, and Fresh!

Bungalow w pickleball/tennis steps from beach

The Palms 1202 - The most expansive ocean views
Private house rentals

Bare Feet Retreat 515B:Walk everywhere + Strong AC

Oceanfront Koa Lagoon Condo w/ Sunset Views

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

New Fall Special Ocean View AC 2 Bed Sleep 5

Unobstructed Oceanfront View | Turtles and Whales!

exquisite condo in KKN #174

Central 3 bed 1 bath Cottage

1Bedroom Condo, Steps from Kamaole Beach/Kihei, HI
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 2,145 | ﺩ.ﺇ 2,420 | ﺩ.ﺇ 2,402 | 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
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- Haleakala National Park
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- Aston Mahana at Kaanapali
- Maui Arts & Cultural Center
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- PacWhale Eco-Adventures
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