Pet-friendly vacation rentals in Kaanapali

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.

4.98 out of 5 average rating, 51 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.

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4.92 out of 5 average rating, 144 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

Outdoor spacesWalkabilityTV

5 out of 5 average rating, 7 reviews

Surf Rider| Remodel • Ocean View • 350 steps Kam 1

🌊 THE SURF RIDER 🏄🏽‍♂️—Step onto your private walk-out lanai and wake up to ocean views from this freshly remodeled Kihei retreat! Nestled between Kihei & Wailea, you’re a 5 minute walk to Kamaole Beach Park 1, world-class dining & both luxury and local shops. Beat the heat with split A/C, then enjoy resort-style amenities: sparkling pool, hot tub, sauna, BBQ grill, pickleball & bocce ball. Whether you’re chasing waves or chasing sunsets, this is your perfect Maui home base. 🌺 Aloha Awaits!

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Superhost

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

4.87 out of 5 average rating, 262 reviews

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!

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4.89 out of 5 average rating, 568 reviews

An open living space features a comfortable bed with soft blue linens, a stylish fold-out loveseat, and a large area rug. A fully equipped kitchen with wooden cabinets and a breakfast bar is visible, complemented by natural light from nearby windows.

Guest suite in Wailuku

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

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Condo in Napili-Honokowai

A serene ocean view captures calm waters reflecting the sky, with gentle waves lapping at the shore. The horizon features distant islands and clouds, creating a tranquil atmosphere. Rocky formations line the shallow water, leading towards the sandy edge, inviting a peaceful exploration.

5 out of 5 average rating, 8 reviews

Tropical Oasis By The Sea

Lush ground floor 2bed 2 bath condo just steps to the ocean. Clean Ocean view. All New chef's dream kitchen with granite counters, fully stocked down to garlic presser. New A/C, comfortable king bed with cotton sheets, new SS appliances. A short walk to restaurants, shops, and markets. This is a really Hawaiian lush ground complex where one can really appreciate why you came to enjoy Maui. Free parking. All bookings require a cleaning fee & Hawaii City & State taxes. Laundry room on-premises.

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4.93 out of 5 average rating, 415 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 12 years with over 1,500 five star reviews. BUT 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: "The Jewel is extraordinary! The views are stunning! I’ve stayed in many Air B&Bs. I give her place my highest rating!" Btw, we have not raised our prices. The service fee now shows.

PetsWalkabilityGetting around

Farm stay in Haiku-Pauwela

The exterior of a private cabin is surrounded by lush greenery, featuring vibrant tropical plants. A porch with rocking chairs offers a welcoming spot to relax. The cabin's distinctive architecture includes a sloping roof and decorative wooden details, providing a harmonious blend with the natural environment.

4.97 out of 5 average rating, 329 reviews

Ocean View - Private Cabin

NOTE: Many oceanfront condominiums are currently under threat of a phase-out. Farm stays are a "Permissible Use" on agricultural bona fide farms by State of Hawai'i law. Be assured your reservation here will be safe from government interference. Located on a working coffee plantation and food forest, this restored cabin is private but close to lots of upcountry activities. Kitchen, ocean view, open concept, great lanai spaces, plenty of off-street parking, access to private hiking trails.

Outdoor spacesWalkabilityBackyard

A stunning sunset is captured over the ocean, with a vibrant orange sun descending towards the horizon. Silhouetted palm trees frame the scene, their fronds gently swaying in the breeze. The calm waters reflect the warm colors of the sky, creating a serene coastal atmosphere.

4.88 out of 5 average rating, 416 reviews

Ocean View - Deluxe Unit #201

AMAZING location 1/2 mile from Wailea one of the most upscale/expensive and prestigious parts of the island, where there are GPA golf courses, and high end shops. You can walk to 13 restaurants, coffee shops, lots of souvenir shops. Snorkeling, boating, all kinds of water sports and sightseeing. And the beautiful Kam II white sand beach is across the street! Kamaole Shopping center is next door, has Coconut's fresh food restaurant, Cones on Maui icecream shop, and much more!

Outdoor spacesWalkabilityAir conditioning

4.92 out of 5 average rating, 13 reviews

Apartment in Maalaea

Steps to Beach Sand & Surf

Aloha! We are your hosts and local Maui residents. We live right here on the island and take great pride in self-managing our units at Maalaea. We love the "Old Hawaii" charm of Maalaea and the central convenience it offers for exploring the island. Whether you need a recommendation for the best local poke or tips on watching the whales from the shore, we are here to help. Our goal is to make you feel like family and ensure your Maui retreat is exactly what you dreamed of.

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A bright living area is showcased with large glass doors offering access to an outdoor space. Comfortable seating is provided by a gray sofa and wicker chairs, accented with blue and patterned cushions. A glass coffee table is placed centrally, complemented by a mounted flat-screen TV.

4.86 out of 5 average rating, 107 reviews

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

Location, Location Location! Right in the middle of all the action in Kihei, Maui. Quick Walk to the Beach, Restaurants, Grocery and Shops. Directly across the street from World Class Beach Kamaole 1. Your Dream Hawaiian Vacation starts at our Comfortable Condo with a Fully Stocked Kitchen, complete with Comfortable beds, Quality Linens, Soft Beach & Bathroom Towels and Split System AC Enjoy the complimentary Welcome snacks upon arrival.

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