Pet-friendly holiday rentals in Wailea

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

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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, 53 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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Superhost

Flat in Kihei

4.91 out of 5 average rating, 11 reviews

THE NEST - Cozy, Quiet - Blocks to Beaches

Your family will be close to everything when you stay at this centrally-located Condo. Explore Kihei by foot. Charlie Young, Kam1, Kam2, and the Cove minutes away . Dining also within walking distance Condo recently renovated with new furnishings and décor. Relax in peaceful Paradise . Quite area on dead end street. Fabulous pool, on site laundry, many amenities for your comfort and excursions. Big bedroom with a king sized bed . Couch can be converted to a full bed . Pets on approval only.

WalkabilityHospitalityBeach

4.83 out of 5 average rating, 110 reviews

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

True Hawaiiana charm, comfort, and convenience for your family vacation. Located in the heart of Maui, in historic Wailuku town, with easy access to all parts of the island for all your planned activities. Beaches within 10 minutes drive time in 3 directions and the beautiful West Maui mountains w/ Iao Valley National park behind. After a day of adventure come home to a restful time in the HOT TUB under the bright stars . Walk to boutiquey stores ,Coffee shops, First Friday party w/the locals

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5.0 out of 5 average rating, 8 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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A private lanai offers an inviting outdoor seating arrangement, consisting of a glass-top table surrounded by four chairs. Lush palm trees sway gently in the breeze, framing panoramic ocean views that extend towards the horizon, showcasing tranquil sea tones under a vibrant sky.

4.94 out of 5 average rating, 69 reviews

Maui Sunset Oasis- Top Unit w/AC

A stunning oceanfront sunset condo in Kihei! This updated top unit 2-bdr, 2-bath with AC offers stunning sunsets from manicured grounds. Step onto the private lanai to unwind and enjoy panoramic ocean views! Take a dip in the pool or stroll to two beautiful beaches. Groceries, coffee shops, and restaurants are a short walk away. Inside, enjoy recent updates, air-conditioned bedrooms, and a fully equipped kitchen. Experience unforgettable sunsets, pristine beaches, and the best of Kihei, Maui.

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A living area is depicted with large sliding glass doors that open to a balcony view of the ocean and palm trees. A ceiling fan rotates gently above a comfortable seating arrangement that includes a light-colored sofa and two armchairs. A wooden coffee table is positioned in front.

4.95 out of 5 average rating, 40 reviews

High-Floor Island Surf | AC | Walk to Beach

Welcome to our cozy condo in the Island Surf Building, Kihei, Hawaii. It is on the 5th floor of this 6-story building, perfect for couples visiting Maui, and conveniently located near key attractions. Right next door to South Maui Gardens, a gem in Kihei where you can enjoy coffee, movie nights, and some of the best food trucks on the island, and across the street from Kalama Park. ★ If you enjoy this listing, click the heart icon ❤ in the top-right corner to bookmark it for easy access!

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4.97 out of 5 average rating, 29 reviews

Luxury condo 20 steps from beach/pool/hot tub #103

Aloha, and welcome to Sugar Beach Resort, Unit 103! This fully renovated (2023) ground-floor condo offers a high-end, fully stocked kitchen, easy walk-out access, and is just steps from Sugar Beach. Enjoy a heated pool, jacuzzi, and dry sauna after a day in the sun. Beach chairs and towels are provided for easy, stress-free beach days. Sugar Beach Resort is centrally located — just 15 minutes to OGG, Costco, Target, Whole Foods, and Walmart, and 30 minutes to Lahaina, Paia, or upcountry.

Outdoor spacesWalkabilityDecor

4.91 out of 5 average rating, 11 reviews

The living room features a comfortable sofa, accent chairs, and a coffee table. Two upholstered ottomans offer additional seating. A large flat-screen TV is mounted on the wall. Sliding glass doors open to outdoor seating, allowing natural light to fill the space.

Flat in Wailea

Paradise! Ground Floor 1BR AC Kamaole lll beach

Kihei-Recently renovated condo., 1 br (very comfortable king size bed) & flat screen TV, 1 ba, living room w/Q sofa bed, lg flat screen TV, wireless modem & high speed internet. Ceiling fans in bedroom & living room. New A/C in bedroom. Fully equiped kitchen loaded w utensils, pots & pans, coffee maker, toaster, microwave & blender. This Gem Condo is all one level. Steps away from the lower pool, bbq, tennis/pickleball courts & of course the beach. I’m available by phone or text anytime.

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A serene beach scene at sunset showcases soft hues of orange, pink, and purple in the sky. Silhouetted figures walk along the shoreline, while a tall palm tree stands nearby, framing the tranquil landscape and creating a sense of calm.

4.84 out of 5 average rating, 431 reviews

Ocean View Superior Deluxe - 200

Superior Deluxe Ocean View 1 bedroom/1 bathroom 580sf recently remodeled, new AC. Bedroom furniture California king size mattress & Sleeper sofa in living room w/memory foam mattress, FULLY equipped kitchen, all appliances and utensils, condiments spices, coffee maker, toaster. Beach towels, chairs, umbrella, boogie board, and some beach toys. Washer/Dryer in the unitl. Everything you will need for a carefree vacation! Unobstructed view of the beach, right across the street. corner unit.

Outdoor spacesWalkabilityPool

4.93 out of 5 average rating, 14 reviews

Flat 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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