Pet-friendly vacation rentals in Wailea

A sandy path leads from lush greenery to a serene beach. Palm trees sway gently in the foreground, framing views of calm blue waters and distant islands under a clear sky with scattered clouds.

4.97 out of 5 average rating, 31 reviews

*Rare Find* Quiet Ocean View Condo in Sunny Kihei

🌺 Aloha! Maui Welcomes You! 🌺 Experience beautiful ocean views, breathtaking sunsets, and Humpback whale activity (Nov-April) from the privacy of your own lanai. This perfectly located slice of paradise in Kihei is only a few short blocks to Charley Young and famous Kamaole beaches. Walk to Kihei's premiere spots to sun, surf, snorkel, paddleboard, shop, and dine. Take your photo with the famous birds of Lahaina who relocated near the gourmet food carts in the beautiful South Maui Garden.

4.92 out of 5 average rating, 131 reviews

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.

Home in Kihei

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

4.98 out of 5 average rating, 115 reviews

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.

Home in Wailea

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

4.88 out of 5 average rating, 248 reviews

An inviting bedroom features a spacious bed with a patterned blanket. Two framed paintings adorn the light blue walls, and a bedside lamp provides soft illumination. A doorway leads to a bright living area, with natural light visible from additional outdoor access.

Apartment in Wailuku

2B/2B Cottage/Cozy/Central/Private/Historic town

2B/2B cottage, in the heart of Maui, in historic Wailuku town... home of the famous Iao theater and minutes from Iao Valley National Park & the famed "Needle Mountain". Private, fully furnished, and equipped with all amenities needed for a comfortable short-term stay. Easy access to Beaches,Airport & all parts of the island within a 10–30 minute drive. It's great for business travelers doing business in Wailuku, Hikers, Bikers, & true Hawaiiana- seeking tourists. Check out Wailuku First Friday!

4.93 out of 5 average rating, 313 reviews

A private rear deck features a shaded area with tropical foliage and bamboo fencing. Two surfboards and beach gear are neatly stored, along with a round table and colorful chairs for seating. A large black container sits in the corner, adding to the functional outdoor space.

Villa in Kihei

Steps from Beach • Park at YOUR Private Back Door

Ground-floor, bottom corner unit across from Cove Beach — close to beach sunset, surf, food trucks, and local stores. The only unit with a tandem parking stall right next to your wall and back deck entrance. Step out of your car, walk straight in to your smart lock security door on your own back deck. Fully upgraded with fast Wi-Fi, two AC units, new appliances, and a lava rock shower with hot, strong pressure. Sleeps 4 with a master + studio, beach gear, well-stocked kitchen, and fresh linens.

4.86 out of 5 average rating, 121 reviews

The image captures a serene beach scene with clear turquoise waters gently lapping against a sandy shore. Distant islands are visible on the horizon under a bright blue sky adorned with soft white clouds. The tranquil ocean setting suggests opportunities for swimming and snorkeling.

Condo in Lahaina

A jewel on Oceanfront & Breath Taking Views.

Now booking 5 Star rated, beautiful oceanfront ground level condo. 12feet from the ocean. Your backyard is the ocean. Enjoy 180% of amazing ocean views plus Molokai & Lanai Islands, awesome sunsets & whale watching. Explore & swim 2 reefs just outside the lanai. You got it all in our renovated private condo. New A/C in all rooms . Walking distance to town. FREE parking 12 steps to the front door. We provide a well-stocked kitchen, snorkeling gear, buggy boards, beach towels & chairs, 2 BBQ.

4.93 out of 5 average rating, 362 reviews

A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.

Home in Kula

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, Kula Jewel, burned to the ground in the Maui wildfires in 2023. We have recently completed building the NEW Jewel, and it is GORGEOUS! We just had our first guests stay, and this was their review: "Pamela’s place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! I’ve stayed in many Air B&Bs; I give her place my highest rating!"

4.85 out of 5 average rating, 125 reviews

Resort Studio w/ 2 Beds-Walk to Beach and Dining!

Escape to paradise in this stylish 2-bed studio, just a 5-minute stroll from Kamaole Beach II. Perfect for friends, couples or small families, this retreat features a kitchenette, and a private patio overlooking lush garden views. We’ve stocked the space with all the beach day must-haves. Set within a resort community, you’ll enjoy sparkling pools, relaxing hot tubs, BBQ areas, and 24-hour security. With restaurants, shops, and island adventures just steps away, its the ultimate getaway.

A wooden sign displaying the name 'Kihei Bay Vista' stands along the roadside, surrounded by green grass. The ocean can be seen in the background, along with distant mountains and a clear blue sky.

4.9 out of 5 average rating, 195 reviews

Newly Updated Clean Condo w/AC! <2min to beach!

Aloha and welcome to Kihei Bay Vista! Enjoy the scenic ambiance in this newly updated 1 bed 1 bath condo located on the peaceful, quiet side of the resort. This gorgeous condo is steps away from Kalepolepo Beach and Turtle Sanctuary! Walk right out of your accommodations and stroll down the beach, watch the gorgeous sunset every evening & enjoy the whales during season. Great proximity to Kalepolepo Beach, Keaka Beach, Waipuilani Park, shopping, restaurants, Maui Nui Golf Club, and more!

A modern living area features a comfortable sofa and a chair, with a flat-screen TV situated on a wooden media console. Large sliding glass doors provide access to a private lanai, with views of palm trees and the ocean in the background.

4.98 out of 5 average rating, 64 reviews

Oceanfront renovated luxury-best location! SBR 404

Aloha! Welcome to Sugar Beach Resort, #404! This beautifully renovated condo is fully equipped for a fabulous Maui vacation, just steps from the soft sand of Sugar Beach, Maui’s 5-mile paradise. Sip your morning coffee with sweeping ocean views and watch humpback whales (Nov–Apr) right from your lanai. Centrally located for effortless exploring—15 mins to OGG, Costco & Whole Foods; 30 mins to Lahaina, Paia & Upcountry—so you spend less time driving, more time in paradise.

4.98 out of 5 average rating, 55 reviews

The cottage exterior presents a light green facade with a sloped roof, complemented by vibrant flowering shrubs. A private carport is visible beside the entrance, and a shaded seating area is provided under an umbrella on the porch. The scene is surrounded by lush greenery.

Cottage in Wailea

Maui Meadows Ocean View Cottage

Our 1 bedroom Ocean view cottage offers the maximum in privacy and convenience. Located in Sunny South Maui, just above the Wailea Resort, our cottage has everything you need to Maui Maui your Home. AC, WiFi, Fully equipped kitchen, covered carport and more... We are a Maui County permited B&B and our quoted price will include Hawaii State and Maui County taxes of 17.42%. Be sure to always confirm if your rental is permitted and if tax is included in the price quoted.