Pet-friendly holiday rentals in Wailea

*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

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

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

40% off monthly stay! 4 Bed Family Home (Kihei)

4 BEDROOMS, 2 FULL BATHROOMS - FULLY REMODELED HOME Located in central Kihei just two blocks from the beach, Starbucks, golf courses, Kalama park, restaurants, movie theater, food trucks, entertainment, Foodland, etc. This property is secured and fully fenced. The common area consists of a driveway, garden and 2 outdoor showers. A/C in all rooms + private outdoor BBQ and laundry. You will be staying in the main house of the property and will have your private parking spot with EV charger.

Sugar Beach Bliss - Best Oceanfront Vacay Ever!

At Sugar Beach Resort, guests will enjoy our NEWLY renovated condo (Summer 2023) fully appointed for a perfect vacay! The Space -YOU'RE ON THE SAND -Lounges Oceanside -Beautiful Ocean and Haleakala views -Sparkling Pool & Jacuzzi -BBQs -Spacious Lanai -Gourmet Equipped Kitchen -King Bed in Master -Queen Sleeper in Living Room -Quiet Central Air -Secure WIFI Internet -New 65" Smart TV in LR -New 36" Smart TV in Bdrm -Full Size Washer/Dryer -Beach Chairs/umbrella/cooler -Pool/Beach Towels

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!

The Lava Shack

Welcome to The LAVA SHACK🌋 The perfect blend of Hawaiian charm & central convenience! It’s the ideal home base for soaking in everything Maui has to offer. Perfectly located between Kihei & Wailea, you’ll be less than 250 steps from breathtaking beaches, great restaurants, & local shops! Tucked away at the end of a quiet cul-de-sac, our place is peaceful, private, and away from street noise. We can’t wait for you to experience our happy place. We know you’ll fall in love. 🌺ALOHA AWAITS🌺

Cozy Cute Condo | Maui Vista | Walk to The Beach

Located on the second floor in the front building of a three-building complex, a newly renovated pool is just a few steps away from the unit. Also steps away are two well-maintained gas barbecues in the common area and championship tennis courts. The condo complex has 3 pools, 3 grill areas and 3 tennis courts. This condo is conveniently located within walking distance to the local super market, stores/shops, restaurants, gorgeous beaches and The Cove, Maui's South shore surf beach.

Mermaid Bungalow, cozy and ready for action.

Come as guests, live like locals Jeep for rent Boards for the morning glass for rent E-bikes for farmers market runs and bike exercise for rent. Your own private local home away from crowded condos ✓ Just bring your sense of adventure. Mermaid Bungalow is special because it is a LOCAL MAUI HOME that is away from the crowded places of condos / apartments. The guests have a chance to assimilate to the true Hawaiian living and to fall in love to the beautiful island of Maui.

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.