Pet-friendly holiday rentals in Wailea

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Guest favourite

Ocean View Superior Deluxe - 200

Superior Deluxe Ocean View 1 bedroom/1 bathroom 580sf recently remodeled, new AC. Bedroom furniture Cal king 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, Washer/Dryer. Unobstructed view of the beach, right across the street. corner unit. Great location in Kihei at Kamaole II beach, proximity to world-class beaches, top-rated golf courses

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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Guest favourite

*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.

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.

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

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.

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!

Top Guest favourite

Guest favourite

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.

Ocean View! Modern, Walk to Beach, Shops, & Pool!

Ocean View Central location in Kihei. Brand New Renovation. AC in every area! One bedroom with King Size bed. Loft with Queen Size Bed. Gorgeous ocean and Sunset view. Watch the Whales at winter at the World famous Kihei beaches in your backyard. Everything you need is within walking distance! 5 min walking distance to the beach, supermarkets, & restaurants. 30 min drive to Lahaina, 5 min to Wailea, & 15 min to Kahului the location of the airport, Costco, Target and Walmart.

Lava Shack | 1BR • 2ACs • 250 Steps to Kam 2 Beach

Welcome to The LAVA SHACK🌋 Your Maui home base between Kihei & Wailea — just 250 steps to Kamaole Beach II, great restaurants & local shops. Stay cool with dual A/C, and the in-unit washer/dryer makes longer stays easy. Tucked at the end of a quiet cul-de-sac: peaceful, private, away from street noise. Lounge at the pool, stroll to the beach, then unwind in your clean, coastal retreat. King bed +fully stocked kitchen! Our happy place is ready to become yours. 🌺ALOHA AWAITS🌺

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.

Private Ocean View Cottage Near Wailea - Sunsets

Wake up to birds chirping, tropical gardens and ocean views. Our private 1 bedroom Maui Meadows Ocean view cottage in Sunny South Maui is just above the Wailea Resort, with world class beaches, golfing, snorkeling and dining. Our cottage has everything you need to make Maui your Home. AC, WiFi, Fully equipped kitchen, washer/dryer, covered carport and more... We are a legally permited B&B. Be sure to always confirm if your rental is permitted to operate in Maui.