Pet-friendly vacation rentals in Wailea, 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, 113 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, 239 reviews

Apartment 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!

4.93 out of 5 average rating, 290 reviews

All-in-1 •Next-2-Parking •Deck Ent. •Lg.W/D •1minB

Aloha! Updated Front Lower Corner Villa! Private. 1 Master- 1 Studio- 1 Bath •Downstairs- South Kihei Rd. Side- Corner Unit with Driveway Parking Connecting to a Private Entrance. •Our Ohana has all needed to feel right at home. (2) Iron Security Door Private Deck Black out curtains New Kitchen Full size WASHER AND DRYER Xtra Linens A/C (2) LED- Mirror Vanity Black Rock Shower 5 Min walk to COFFEE & Restaurants 3 Min Walk- Beachs, Cove And Charley's Plenty of USB- 500+ Net Beach equipment

4.89 out of 5 average rating, 208 reviews

Beachside Bliss,Couples Retreat, New AC, $139

Summer $139. You'll love it! New split AC offers a cool, peaceful sleep. Full kitchen, bbqs for preparing picnic meals. Our 'studio only' complex is perfect for couples. Our private entry, corner unit is surrounded by tropical plantings, double lanai, full kitchen. 80 Steps to 14 mi of beach, sunsets, turtles. Super clean and comfortable. We are so proud of our 5☆ reviews. Guests love our quiet, central location. Resort fun, large pool, hot tub, bbq, tennis. Golf, pickleball close by.

Superhost

Condo in Lahaina

4.91 out of 5 average rating, 44 reviews

5 Star Best, Best Beaches, Golf & Views

Now booking amazing view vacation destination at El Dorado Resort. Our 5 star spotless 2 bed 2bath en-suite condo sleeps up to 8 guests. Enjoy our uncrowded world renowned clean beaches & snorkeling by Black Rock. Our large 1500 Sq. Ft. condo offers 3 pools, a gym, a huge private lanai, a FREE trolley that will take you to & from Whalers Village, fine shops & restaurants. Our beach cabana offers fresh towels, lounges & chairs plus a fully equipped kitchen, showers and bathrooms for your use.

4.92 out of 5 average rating, 338 reviews

Home in Kula

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, 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: "Pamela’s place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! I’ve stayed in many Air B&Bs; I give her place my highest rating!"

4.95 out of 5 average rating, 22 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!

Superhost

4.83 out of 5 average rating, 114 reviews

Condo w/ Resort Amenities -Walk to Beach, WiFi, AC

Stroll a lush garden path to Kamaole Beach II from this stylish Maui Banyan studio! Featuring 2 double beds, a modern bathroom, kitchenette, and private balcony with tropical views. We provide beach gear—boogie board, umbrella, chairs, cooler and a wagon to haul it all! Enjoy resort amenities—2 pools, 2 hot tubs, tennis, BBQs, and free parking. Walk to beaches, dining, and shops—everything for a perfect Maui getaway! We will be happy to answer any other questions, feel free to reach out!

4.96 out of 5 average rating, 27 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.

4.98 out of 5 average rating, 51 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.