
House holiday rentals in Wailea
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Top-rated house rentals in Wailea
Guests agree: these houses are highly rated for location, cleanliness and more.

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu
Tranquil Beachfront Estate w/ 5 Luxurious Private Full Suites & Exotic Fruit Grove. Full amenities. Our luxury Beachfront estate has 4 beachfront one-bedroom suites and a garden view two-bedroom Ohana. Each suite has a private entrance, separate living room, full kitchen and is like having your own condo at the beach in Maui. This special place is hidden behind a private, double gated entrance, lined with 700 ft of lighted coconut palms that lure you into the feeling of leaving the world behind.

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

40% off monthly stay! 4 Bed Family Home (Kihei)
4 BEDROOMS, 2 FULL BATHROOMS - FULLY REMODELED HOME Located in central Kihei just two blocks from the beach, Starbucks, golf courses, Kalama park, restaurants, movie theater, food trucks, entertainment, Foodland, etc. This property is secured and fully fenced. The common area consists of a driveway, garden and 2 outdoor showers. A/C in all rooms + private outdoor BBQ and laundry. You will be staying in the main house of the property and will have your private parking spot with EV charger.

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

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

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

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

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Luxe 3BR Pualei Beach House Retreat

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

exquisite condo in KKN #174

3 Bedroom Private House Kihei /Wailea Maui

Oceanfront Koa Lagoon Condo w/ Sunset Views

1 Bedroom Beach

Central 3 bed 1 bath Cottage

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

Brand New 2 Bed/ 1Bath Cottage
Private house rentals

Chic Villa 6 – Beach Vibes & Walkable Paradise!

Chic Villa 2 | Modern Vibes by the Ocean

Ocean Front Cottage, 30 steps to the beach!

Aloha Aku Hula2 Suite – Beachfront Bliss

PAIA HALE Walk to beach and town

1 Bedroom Villa with Ocean Views, Steps to Beach

Aloha Aku Honu Suite – Experience the Spirit of Al

Aloha Aku Bamboo Suite – Discover Beachfront Seren
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 | $635 SGD | $689 SGD | $619 SGD | $635 SGD | $635 SGD | $514 SGD | $516 SGD | $571 SGD | $571 SGD | $635 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
- Kapalua Bay Beach
- Polo Beach
- Wailea Beach
- Maui Ocean Center
- Hāmoa Beach
- Ka'anapali Golf Courses
- Ulua Beach
- Old Lahaina Luau
- Big Beach
- Whalers Village
- Black Rock Beach
- Haleakala National Park
- Peahi
- Maui Vista Condominium
- Maui Arts & Cultural Center
- Black Sand Beach
- Kihei Kai Nani
- Kahana Beach
- Maui Sunset
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