Pet-friendly holiday rentals in Wailea-Makena

4.92 out of 5 average rating, 131 reviews

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

4.98 out of 5 average rating, 108 reviews

Home in Kihei

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

4.87 out of 5 average rating, 232 reviews

Flat in Wailuku

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!

5 out of 5 average rating, 7 reviews

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

4.86 out of 5 average rating, 105 reviews

Steps to Beach AC/Pool Views/Kitchenette/WiFi

Just steps from the beach! Relax in our renovated, centrally-located studio condo at the Maui Banyan Resort. Located only a short garden path walk from Kamaole Beach II, you can often enjoy sea life sightings. Take advantage of the included beach gear, such as chairs, boogie boards, umbrella, and wagon for your convenience. Experience resort-style amenities, including tennis courts, free parking, two pools with hot tubs, BBQs, umbrellas, and restrooms. The perfect spot for your Maui getaway!

5 out of 5 average rating, 16 reviews

High-Floor Island Surf Condo | AC | Steps to Park

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!

4.98 out of 5 average rating, 49 reviews

Oceanfront renovated luxury-best location! SBR 404

Aloha! Welcome to Sugar Beach Resort, #404! This newly and luxuriously-renovated unit has all you need for your perfect Maui vacation: incredible ocean sunset views and just steps from crystal clear Sugar Beach. During whale season (Nov-April), you can see humpback whales from the condo! 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.

4.95 out of 5 average rating, 20 reviews

*Rare Find* Quiet Ocean View Condo in Sunny Kihei

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 south 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. Have your photo taken with the famous birds of Lahaina who relocated to the gourmet food cart area inside the beautiful South Maui Gardens.

5 out of 5 average rating, 6 reviews

Hip Hawaiian Seaside Vistas

Spacious and elegant. Completely remodeled in November 2024, no expense was spared to create our gorgeous oceanfront oasis. This two-bedroom, two-bathroom condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is within reach. Beach chairs, umbrellas, plush towels and a cooler are all provided. Whether you dine out at a delicious local restaurant or play chef in our fully stocked kitchen, you will love your new home away from home.

4.85 out of 5 average rating, 73 reviews

Kihei Bay Vista - #C204 - Maluhia Beach

A peaceful Maui gem just steps away from the ocean. 1 bedroom - 1 bathroom - & sofa sleeper condo located in South Maui. It has beautiful cathedral ceilings giving the condo a spacious feel. Tile flooring throughout, and a remodeled bathroom with granite counters and a walk in shower. The updated kitchen has granite counters as well. Large bedroom with a queen sized bed has a spacious walk in closet and vaulted ceilings. Video: https://vimeo.com/529663166?ref=em-share

4.98 out of 5 average rating, 50 reviews

Cottage in Kihei

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.