House holiday rentals in Wailea

A patio area features a light-colored chair and a round table, overlooking a grassy lawn that leads to the ocean. A tree with twisted branches is visible in the background, along with several upright, leafy plants. The inviting blue water of a pool can be seen beneath the sunlit sky.

4.88 out of 5 average rating, 16 reviews

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.

A cozy outdoor deck is showcased, featuring two wicker chairs and a small table, inviting relaxation. The inviting turquoise door stands adjacent to a wall with the word 'Aloha' elegantly displayed. String lights add a warm touch above, surrounded by tropical greenery.

4.92 out of 5 average rating, 131 reviews

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

4.92 out of 5 average rating, 13 reviews

Romantic Oceanview Condo Steps to Beach

Escape to your perfect Hawaiian retreat in this charming one-bedroom Maui condo, just steps from the beach. Enjoy ocean views from the large corner lanai, a spacious living area with bamboo floors, comfortable couch, and large flat-screen TV with bluetooth soundbar. A modern kitchen and elegant master bathroom with a tile shower add to the luxury. The fully stocked amenity closet includes beach toys, chairs, snorkel gear, umbrellas, bocce balls, boogie boards, and a cooler for all your seaside a

The exterior of a spacious home is framed by lush tropical plants and trees. A charming pathway leads to a welcoming front deck illuminated by soft lighting. Large sliding doors enhance visibility into the interior, where comfortable seating is visible in a cozy living space.

4.98 out of 5 average rating, 117 reviews

Mana Hale Vacation Rental

This private home is nestled in a beautiful garden just 1 mile from the ocean. The house is spacious with 2 bedrooms & 2 full bathrooms. Front and back decks offer ample opportunity for lounging with a good book, grilling, visiting with friends and family or even just a romantic getaway. The house is close to cafe's, shopping, restaurants and many of the idyllic maui beaches. Perfect for retreat, fun and healing in paradise. STKM 2018/0002 HITax # GE-087-066-3168-01 HI TAT # TA-087-066-3168-01

A spacious living area showcases natural wooden elements, with a light-colored bamboo sofa and matching chairs. Large glass doors frame a stunning seaside view, allowing soft light to illuminate the room. A ceiling fan provides ventilation, complementing the relaxed ambiance of the space.

5 out of 5 average rating, 17 reviews

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.

A spacious living area features a comfortable grey sofa and a wooden coffee table. A dining table with four chairs is positioned nearby. Bright artwork depicting tropical leaves adorns the wall. The open kitchen includes modern appliances, illuminated by soft overhead lighting.

4.98 out of 5 average rating, 43 reviews

Kihei Stay: 5 Min walk to Beach, Steps to Pool, AC

Welcome to our 1-bed, 2-bath condo just steps from the pool and ocean in South Kihei! Enjoy a spacious living area with a queen Murphy bed, full kitchen, desk, cozy bedroom with a king bed, and two full bathrooms. Lounge by the pool, BBQ, or take a 4 min walk to Kam III for a sunset, whale watching, boogie boarding, and snorkeling. Kam III has picnic tables, swings, and spots to hang a hammock. Several restaurants are walking distance. Experience the beauty of Kihei from this great location!

A spacious single-story home is surrounded by lush palm trees and vibrant tropical plants. The well-maintained lawn features a mix of greenery, with the house's exterior displaying a neutral tone under a bright blue sky.

4.85 out of 5 average rating, 164 reviews

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 kitchen features light-colored cabinetry paired with granite countertops and stainless steel appliances. A large refrigerator and microwave are visible, along with an oven and stove. A central island with a wooden top provides additional workspace. Soft lighting enhances the functional layout.

4.97 out of 5 average rating, 152 reviews

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

The covered private lanai is depicted, featuring seating areas with outdoor couches and ceiling fans. A well-maintained lawn leads up to the entrance. Bright blue skies and soft clouds frame the space, creating a serene outdoor environment for relaxation.

4.83 out of 5 average rating, 106 reviews

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!

4.93 out of 5 average rating, 178 reviews

PAIA HALE Walk to beach and town

This sweet cottage sits on a flag lot, gated and fenced, shared with my 2 bedroom cottage. Parking is directly in front of the cottage. New kitchen as of July, 2025. There is a nice outdoor area with table, chairs and barbecue. Coolers and beach chairs are also provided. (Please note, I only advertise or book this condo through Vacation rental sites. If someone has approached you to book this directly, it is a scam.)

4.96 out of 5 average rating, 442 reviews

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

The exterior of a charming home is highlighted, featuring a distinctive turret and surrounded by lush greenery. Palm trees and flowering plants add to the tropical ambiance. The welcoming porch is framed by columns, inviting guests to enjoy the natural surroundings.

4.89 out of 5 average rating, 164 reviews

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.

Popular amenities for Wailea house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A bright living area is presented with large glass doors offering views of the ocean. A dining table made of wood is accompanied by light-colored chairs. A potted plant and a unique wood side table add natural elements, while pendant lights provide soft illumination.

4.69 out of 5 average rating, 32 reviews

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

A cozy outdoor patio is shown, featuring a round table surrounded by two modern chairs. The view includes well-maintained grassy fields and tall palm trees swaying gently in the breeze, with the ocean in the background under a clear blue sky.

Gorgeous Views! - Kihei Surfside #109

A private balcony features a wooden table surrounded by four chairs, with a serene view of lush greenery and palm trees. Bright sky and the distant buildings of the resort can be seen, suggesting a peaceful outdoor setting.

4.97 out of 5 average rating, 34 reviews

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

Walk to the Beach, Balcony w/ View, Communal Pool

A refreshing swimming pool is surrounded by lounge chairs, set among tropical palm trees. The water's surface reflects the nearby buildings and sky, creating a serene atmosphere. The pool area is designed for relaxation and enjoyment.

4.97 out of 5 average rating, 62 reviews

Centrally located and steps to the beach!

4.97 out of 5 average rating, 39 reviews

A relaxed living area features a blue sectional sofa with red and white decorative pillows. A coffee table sits in front, and a work desk is positioned near a glass sliding door that provides views of the ocean and surrounding palm trees.

Home in Wailuku

Maalaea Kai 307 - Maui Prime Oceanfront

Lush green lawns are framed by tall palm trees, leading to an unobstructed view of the ocean in the distance. A serene pond is visible among the greenery, enhancing the natural beauty of the landscape.

5 out of 5 average rating, 6 reviews

Kamaole Sands FRONT ROW OCEAN Unit 116

Condo in Wailea-Makena

New place to stay

Ground-Floor Gem in Wailea Ekahi Village

Weekly house rentals

A serene view showcases palm trees standing against a clear blue sky, overlooking the ocean. Lush greenery and colorful flowers are visible in the foreground, creating a vibrant contrast to the tranquil blue waters in the distance.

Wailea Ekahi 6E Island Time!

An aerial view captures the layout of the complex, featuring red-roofed buildings surrounded by lush greenery and palm trees. The turquoise pool glistens under the sun, with a nearby open lawn area. A scenic ocean view stretches into the horizon, enhancing the natural beauty of the location.

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

A serene beach is presented, featuring soft golden sands and clear turquoise waters gently lapping at the shore. A distant island is visible on the horizon under a bright blue sky, enhancing the peaceful coastal scenery.

4.65 out of 5 average rating, 249 reviews

exquisite condo in KKN #174

Aerial view of the oceanfront beach house positioned near a rocky shoreline. Waves break across the water, and surfers can be seen in the distance. Solar panels are installed on the roof, indicating a focus on sustainability.

Home in Wailuku

Charming Direct Oceanfront North Shore Beach House

A cozy living area features a light-colored sofa adorned with blue and white cushions. Two patterned armchairs complement the space, while a round wooden dining table sits nearby. Natural light enters through sheer curtains, and a colorful wall art piece adds visual interest.

4.92 out of 5 average rating, 217 reviews

Paia cottage walk to town and beach

Sand +Surf! Brand New

A modern bathroom features a tile shower with a built-in tub and a light-colored shower curtain. A white vanity with a countertop is complemented by potted plants, and a toilet is positioned in the background, creating a clean and functional space.

Home in Kahului

Brand New 1bed/1Ba

Home in Wailuku

New place to stay

Central 3 bed 1 bath Cottage

Private house rentals

A serene outdoor area includes smooth stone dipping pools and a Jacuzzi with sunset views. Tropical plants are situated in decorative pots, complementing the landscape. The setting is enhanced by tiki torches, and a lush lawn extends towards the horizon under a soft evening sky.

5 out of 5 average rating, 3 reviews

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

A covered balcony features a circular table surrounded by four colorful chairs. Sunlight streams in from the left, creating a bright atmosphere. Lush greenery and palm trees can be seen in the background, with a view of the ocean visible beyond.

4.86 out of 5 average rating, 64 reviews

Hale Hookipa Kai House, County Licensed

A serene view features two carved wooden tiki figures positioned amidst a lush green lawn, leading towards a sparkling blue ocean in the background. Delicate orange flowers are visible in the foreground, adding a touch of color to the tranquil landscape.

5 out of 5 average rating, 18 reviews

Aloha Aku CoCoPalm2 Suite – Cozy Beachfront Escape

An open-concept kitchen and living area features a counter with seating for four, complemented by a wooden dining table for four. Sunlight floods through large sliding glass doors, illuminating stylish furnishings and a lush green lawn visible through the patio area.

4.91 out of 5 average rating, 90 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

The beachfront estate is presented from a distance, showcasing its two-level structure surrounded by lush greenery. Large glass doors reveal the inviting spaces within, while a spacious lawn leads to the sandy beach. Solar panels are visible on the roof, emphasizing sustainability.

5 out of 5 average rating, 7 reviews

Aloha Aku Hula2 Suite – Beachfront Bliss

A spacious living area showcases elegant tile flooring and large sliding glass doors that invite natural light. A comfortable sofa is paired with a glass coffee table, while a flat-screen TV is mounted on the wall. A private outdoor space is visible through the doors.

4.85 out of 5 average rating, 13 reviews

Maui Sunset A102 - Aloha Mai 2, Beachfront Resort

An outdoor lanai features a wooden table with two matching chairs, offering a view of manicured lawns and tennis courts. Lush greenery and palm trees frame the scene, while the ocean can be seen in the distance under a clear blue sky.

4.75 out of 5 average rating, 8 reviews

Remodeled One BD Ocean, AC,wifi, pool D202

A peaceful outdoor water feature is surrounded by lush palm plants in decorative pots. Water flows gently from stone elements into a serene pool, with a backdrop of green grass and distant mountains. The setting evokes a sense of tranquility and connection with nature.