Holiday rentals with a pool in Wailea

4.98 out of 5 average rating, 116 reviews

Ground Floor | Building 1 | Across the Best Beach

❖ Bldg 1 closest to ocean of 3 resort buildings ( 2-3 minutes walking) ❖ Newly remodeled the entire condo ❖ Sparking new & clean bathroom ❖ all NEW furnitures, New strong 2 AC ❖ Ground Floor, no stairs ❖ all tiles flooring , clean and germ-free ❖ 1 FREE parking ❖ washer & dryer in unit ❖ 300+mbps Wifi ❖ beach chairs, cooler, beach umbrella ❖ all photos were taken by IPHONE (photo shows what you will see). ❖ 24/7 response during your stay! Hosted directly by the home owner than 3rd party/agent!

4.95 out of 5 average rating, 209 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.

4.99 out of 5 average rating, 195 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! Mana Kai is a hotel zoned resort in an ideal location, right on the border of Wailea and Kihei! Our condo is designed 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, stay with us! We have the best Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!

4.95 out of 5 average rating, 110 reviews

Spacious S. Kihei Suite New A/C across from Kam 3

This spacious suite is perfect a relaxing stay for two. Brand new split system A/C in bedroom & living room to keep you cool. Peak-a-boo ocean views from the suite with glimpses of Kahoolawe. Located in S. Kihei across from one of the BEST beaches on Maui, Kamaole Beach III and steps from the Kihei Boat Ramp. Walk to shops and restaurants in South Kihei. Keawakapu Beach and Wailea is just minutes away. Choose from 2 pools or play a round of tennis or pickle ball. Large lawns and BBQ areas.

Apartment in Wailea-Makena

4.94 out of 5 average rating, 291 reviews

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, 171 reviews

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

4.99 out of 5 average rating, 117 reviews

Wailea Ekahi Oceanview, Beachfront King Bed Studio

Wailea Ekahi is a luxurious beach front resort offering the best of Maui and sunny Wailea. Unit 16B is a renovated ocean view studio unit with a King sized bed and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens. The resort fronts directly onto Keawakapu beach with miles of golden sand; perfect for walking, swimming and snorkeling. 16B is mid property and a short walk to the beach and one of the 4 pools.

5 out of 5 average rating, 221 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

4.95 out of 5 average rating, 133 reviews

Flat in Kihei

Wailea Couples Retreat, 300 FT To Keawakapu Beach

Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

4.96 out of 5 average rating, 109 reviews

Upscale and Elegant Vistas

Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled in September of 2021, no expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

4.98 out of 5 average rating, 169 reviews

Live, Love, Loft in Beautiful Maui

Experience the beautiful island of Maui and all its wonder in this modern loft in Central Kihei. You’re just minutes away from stunning beaches, local markets, and some of the best food on island. Nothing feels like you’ve arrived in Maui like the welcoming sand and warm waters of Charlie Young Beach, just across the street. Head down to The Cove to surf or paddle board with the locals. Or simply relax, put on a classic record and enjoy the sunset from the balcony.