Pet-friendly holiday rentals in Kaanapali

*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.

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

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

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!

Oceanview, Banana Bread, Hot Tub & Sauna near OGG

Serene, Beachy decor. Awaken to Sunrise over Haleakala & North Shore, listen to surf and local birds, and watch the ocean and harbor action- Surfers, Kiters, Sailboarders, Kanaha beach from the secluded back yard. Relax in the hot tub and sauna. Very Central, but you’ll want a car or Uber to get to most places- Wailuku town is 1 mile. Hosts live on-site for needed assistance, otherwise allow guests to enjoy their peace and solitude during the evenings after the day's adventures. FAST Internet

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.

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!"

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.

Haiku Jungle 2: Cozy Ocean View Condo

This cozy, quaint island one bedroom condo with peekaboo view of the ocean, is perfect for traveling professionals. This space is comfortable for 1 couple or a couple with 1 child. The property spans a total of 2 acres and contains 2 buildings with a total of 5 rental units. Full-time renters on site. Dog + cat on grounds. Property common spaces are shared. Located in the quaint Haiku neighborhood nestled between Makawao and Paia - on a less busy, more laid-back side of the island.

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.

Luxury condo, 20 steps from beach/pool/hot tub-103

Aloha, and welcome to Sugar Beach Resort, #103! This fully renovated (2023) unit has everything you need: a high-end kitchen, ground floor access, and just steps from crystal clear Sugar Beach. Did I mention a heated pool, jacuzzi, and dry sauna? Want to explore Maui? The property is the most central on the island, just 15 minutes to the airport (OGG), Costco, Target, Whole Foods, and Walmart. 30 minutes lands you in Lahaina, Paia, or upcountry.

Resort 2-Bed Studio- Steps to Beach/Shops/Dining

Escape to paradise at this stylish 2-bed condo just steps from Kamaole Beach II. Enjoy a private patio with lush garden views, resort amenities like pools, hot tubs, BBQs, tennis court and all the beach gear you need for a perfect Maui getaway. Ideal for couples, friends, or small families seeking comfort and island adventure. Pet Friendly! Free Parking! 24/7 Security on premise. I am happy to answer any questions you have.