Family-friendly vacation rentals in Wailea, Wailea-Makena

4.95 out of 5 average rating, 207 reviews

Maui's Best - Wailea Ekahi 47A

Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

4.94 out of 5 average rating, 283 reviews

Condo in Wailea-Makena

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

4.99 out of 5 average rating, 184 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on incredible Keawakapu beach! This location is ideal, right on the border of Wailea and Kihei. We have designed our remodel with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5-star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach come stay with us! We have hired the best Property Manager in Maui, Tracy O'Reilly to take care of our guests

Superhost

4.87 out of 5 average rating, 235 reviews

Ocean Bliss: Beach Condo - Walk to Everything!

Amazing Ocean View Designer Condo - Fronting world’s best beaches! Full kitchen, Remodeled, Four Seasons King bed, Huge Ocean Views, huge balcony! Non-smoking bldg. Walk to everything (no car needed!) – food, drinks, surf/sup, dive, beach, snorkeling, skating, playground, volleyball, tennis, basketball and more! Views of the islands, whales! Fastest internet speed. Love posting photos/vids on socials Maui Surf Condo. Check it out :). Construction is completed *Please message for discounts

4.95 out of 5 average rating, 153 reviews

Condo in Wailea

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.

4.9 out of 5 average rating, 189 reviews

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

4.84 out of 5 average rating, 303 reviews

★Couples Paradise w/ Lanai★ 3 min. walk to beach!

This 1 bedroom condo is in a perfect central coastal location on Maui in Kihei. It's simple just like island living should be! The complex is right across the street from Kamaole Sands Beach II which hosts amazing Maui sunsets. Snorkeling, dining & shopping are walking distance. The walk to the beach takes only about 3 minutes, if that. Quiet Lanai to enjoy your morning coffee and listen to the birds. Plenty of beach equipment to use during your stay as well!

4.92 out of 5 average rating, 212 reviews

Condo in Wailuku

Rare Beachfront Ground floor Oceanview from Lanai!

Enjoy a Romantic yet affordable Direct BeachFront, Ground floor condo with a partial ocean view from the Lanai. NOT ACROSS THE STREET FROM THE OCEAN! Located on gorgeous Sugar Beach, Maalaea- the LONGEST WALKING BEACH on the entire island. Humpback Whales (Nov-April) and turtles are often seen in the waters. On a a quiet, non-through road, this is like your own little neighborhood paradise! GE-210-827-7760-01 TA-210-827-7760-01 General Excise/Transient Tax

4.96 out of 5 average rating, 430 reviews

Home in Kihei

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

4.98 out of 5 average rating, 118 reviews

Townhouse in Wailea

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Welcome to Happy Everything! Wailea Ekolu Complex A fun, fully re-modeled, well appointed and comfortable townhome situated on hole 10 of the famous Wailea Blue Golf Course at beautiful Wailea, Maui. Comfortably sleeps 6. Spectacular views of the Ocean and Neighbor Islands. Close to beaches, shopping, restaurants, Wailea Resorts and just a chip shot away from the golf course and brand new Wailea Village shops.

4.98 out of 5 average rating, 125 reviews

Condo in Wailea-Makena

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.