
House holiday rentals in Wailea
Find and book unique houses on Airbnb
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

Keawakapu Beach Cottage
A restored cottage just a short walk from Maui's Keawakapu Beach, the best sandy swim beach. We offer a local experience for visitors who want privacy and space adjacent to Wailea Resort amenities including restaurants, golf, spas, shopping and a 3-mile-loop beach walking path. Walking distance to public transportation. We invite you to enjoy our corner of paradise where sunshine meets the sand and surf, and where you are sure to create lifetime memories. MMC-1 STKM 2015/0005 TAT #037857689601

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 custom 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 recently. 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.

Mermaid Bungalow, cozy and ready for action.
Come as guests, live like locals Jeep for rent Boards for the morning glass for rent E-bikes for farmers market runs and bike exercise for rent. Your own private local home away from crowded condos ✓ Just bring your sense of adventure. Mermaid Bungalow is special because it is a LOCAL MAUI HOME that is away from the crowded places of condos / apartments. The guests have a chance to assimilate to the true Hawaiian living and to fall in love to the beautiful island of Maui.

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

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou
Explore paradise in this oceanfront resort's ground floor 1-bed/2-bath condo, beautifully updated with new furniture. Sleeps 5 with a king bed, queen sleeper, and twin Murphy bed. Family-friendly, full kitchen, AC, in-suite washer/dryer, free WIFI, parking, and flat-screen TV. Enjoy a private covered lanai, pool, tennis, and BBQs. Easy self-check-in, centrally located near shopping and restaurants, with a lovely beach right outside the complex.

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet
**NEW OWNER, SAME GREAT CONDO AND EXPERIENCE** Welcome to your serene Kihei oasis. Perfectly located between Kihei and Wailea, this stylish condo is walkable to beaches, sunsets, local eats, and the pool—yet tucked away on a quiet cul-de-sac with no street noise. Enjoy a bright, coastal space, fully stocked kitchen, beach gear, Roku, Bose speaker, and brand-new bedroom AC plus AC in the main living area. Relax, explore, repeat.

Stunning ocean view, heated pool at home by Wailea
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

5 Star 4 Bdrm Private Home in Kihei! 2 K 2 Q
We are new to Airbnb!! 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

Villa Parthenope in Paia bnb #3 *****
Permit n. : BBPH (PHONE NUMBER HIDDEN) (for the permit nuber look at the pics) Prices are inclusive of taxes. Lovely and Romantic home with private bath in Paia, about 7/8 min. walking distance from the beaches and all the services in town.Private entrance. Kitchen corner with hot plates, coffee machine, mini oven, microwave,fridge, blender, and all that you need to cook at home. We DON’T accept kids to this property.

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 house rentals in Wailea
House rentals with a pool

Kihei 533- A/C, Free Parking, and WiFi

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

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

A201a-The closest Maui Banyan studio to the beach

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

The Palms 1202 - The most expansive ocean views

CLOUD 9 BEACH HOUSE Walk to Beach, Oceanview Clean
Weekly house rentals

S. Kihei 2br/2ba - 650' to Ocean

Chic Villa 2 | Modern Vibes by the Ocean

exquisite condo in KKN #174

Ocean Front Cottage, 30 steps to the beach!

PAIA HALE Walk to beach and town

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Central 3 bed 1 bath Cottage

Oceanfront 2BR w/AC - Walk out to Beach!
Private house rentals

Chic Villa 6 – Beach Vibes & Walkable Paradise!

Aloha Aku Ohana2 Suite – Relaxing Garden Views Awa

1 Bedroom Villa with Ocean Views, Steps to Beach

Aloha Aku Honu Suite – Experience the Spirit of Al

Aloha Aku Hula Suite – Find Peace by the Shore

Beautiful One bd Ocean AC,wifi,pool A102

Aloha Aku Bamboo Suite – Discover Beachfront Seren

Stunning Ocean Two Bd Corner Condo,AC,Pool D301
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $507 SGD | $507 SGD | $636 SGD | $690 SGD | $620 SGD | $636 SGD | $636 SGD | $515 SGD | $516 SGD | $572 SGD | $572 SGD | $636 SGD |
| 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 |
Quick stats about house rentals in Wailea

Total holiday rentals
Explore 50 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 2,120 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Wailea holiday rentals include wifi access

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

4.9 Average rating
Wailea stays are highly rated by guests – averaging 4.9 out of 5!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Polo Beach
- Kapalua Bay Beach
- Wailea Beach
- Maui Ocean Center
- Ka'anapali Golf Courses
- Hāmoa Beach
- Black Rock Beach
- Old Lahaina Luau
- Ulua Beach
- Big Beach
- Maui Vista Condominium
- Whalers Village
- Haleakala National Park
- Peahi
- Black Sand Beach
- Maui Sunset
- Maui Arts & Cultural Center
- Kihei Kai Nani
- Kahana Beach
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