Family-friendly holiday rentals in Wailea

A.R.A Retreats: The Molokini

FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

Location and views are everything when it comes to this home. Nestled in the heart of Wailea, most consider the beautiful area of Maui. This RARE 3br/2ba villa has enough space for a large family or a group of good friends. Just a short walk to some of the most beautiful beaches in the world, World class shopping mall and 5 star resorts. Enjoy all the comforts of home while taking in breath taking Grand views of the Deep Blue Pacific, Hole 2 of the Blue Wailea Golf Course and Mount Haleakala.

Oceanfront Kihei Condo Free SUP & Resort Pools!

This beautifully appointed 800 sq ft ground-floor condo features free paddleboard (a $50/day value) just 200 steps from sand. Enjoy resort-style amenities including a sparkling pool, soothing hot tub, kiddie pool, and pickleball courts nearby. Marvel at whale sightings (Dec-Apr) from your lanai or kitesurfing from shore. Stay productive with blazing 500 Mbps fiber WiFi and unlimited AC. We provide beach gear, parking, aon-site laundry. Our prime Kihei location offers the ultimate Maui escape

Locally Owned & Managed - Grand Champions Villa

Our locally-owned, newly redesigned 2BD/2BA modern Maui condo is located on the award-winning Wailea Blue Golf Course at The Grand Champions Villas. The Villas are nestled in the heart of tropical Wailea; minutes from shopping, tennis, restaurants and pristine beaches. Stroll to upscale boutiques and restaurants, or take a short walk to some of the most beautiful beaches in the world. Our condo features local Hawaii art and is your perfect home away from home on the beautiful island of Maui.

Spectacular Ocean View condo beautiful inside out.

Beautiful Inside Out w/ Spectacular Ocean Views from upstairs and downstairs, 2 bedroom 3 bathrooms 2-story townhouse on the Blue Golf Course with over 1500 Sq. ft. of living space + 2 large lanais. It’s located at the 1st row of condo across from the Grand Wailea and Shops At Wailea and only 3 minutes walk to the main shopping center of Wailea. There are retail shops and restaurants right next door. More beaches, restaurants, spas, and hotels are all within walking distance.

Summer Special! - One Bedroom, Closest to beach!

We're happy to assure you that our condo in South Maui is fully compliant and properly zoned for short-term rentals. Book with confidence! As Maui residents, my wife and I can truly say there is no better place to live or vacation than Maui Banyan.. We bought our condo with a long-term goal in mind.. retirement later but fun now. We ask that if you choose to stay with us that the rental agreement that will be sent to you is respected and followed. Welcome to paradise!

Maui Banyan 1BR With View Across from Beach

**PLEASE READ FULL DETAILS B4 BOOKING In order to reduce the fees and taxes, the $160 cleaning fee is NOT included in total and will be collected separately. This quiet Maui Banyan Top-Floor 1BR/1BA condo includes: •HOTEL ZONE - not affected by proposed short-term rental ban •Elevator •Split A/C •Smart lock access •Views of the ocean, West Maui Mtns and Haleakela •5-minute walk to Kamaole II beach •Beach gear •Free assigned parking •Walk to restaurants and shopping

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

130K Hawaiian Reno on Wailea Blue Golf *Ocean View

BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.