Holiday rentals with outdoor seating in Wailea-Makena

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Top-rated rentals with outdoor seating in Wailea-Makena

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Guest favourite

Home

4.96 out of 5 average rating, 409 reviews

Stunning ocean view, heated pool at home by Wailea

Last minute bookings 5 days before arrival, and week long stays are 10% off. 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

Guest favourite

Apartment

4.96 out of 5 average rating, 104 reviews

Romantic Beach Retreat, New King Bed & A+ Wi-fi

Hale Kamaole: Romantic Bright & Airy Beach Condo Across The Street from Kamaole III Beach in South Kihei! Tasteful heritage decor, fast internet, King bed, walk-in shower, 1st floor unit. Perfect for couple's getaway, anniversaries, honeymooners. Washer/Dryer. Spacious lawns & tropical gardens w/ 2 pools, Tennis court & BBQ grills. Popular snorkeling area. Eddie Pu walking trail w/ plenty of wildlife just steps away. Walk to shops & restaurants.Free Parking Pass NB:17.712% Hawaiian Transient Tax

Guest favourite

Apartment

4.93 out of 5 average rating, 158 reviews

Stunning ocean view! 2/2 in the heart of Wailea

FALL SPECIAL November and December - All prices in the $200’s! Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this condo is in the Wailea Resort area, and does not infringe upon nor remove housing from the local neighborhoods of Maui.

Guest favourite

Guest house

5 out of 5 average rating, 224 reviews

Standalone Guesthse 180° View Private Hot Tub

PRIVATE LUXE w100% 5-star reviews! 500ft above sea level on Haleakala above Wailea. 1-BR, 1.5 bath SkyGuesthouse w unparalleled 180+ocean views+islands beyond. You+your beloved in our luxurious space, stargazing, hot-tubbing, sunset watching. Romantic+sensual. L/T rental -Standalone home 704 sq ft -Private hot tub+outdoor cabana drapery -300 sq ft deck w/dining+seating -Private entrance -180-degree ocean views -Large gourmet kitchen/living room -Bedroom, king bed, en suite full bath -1/2 bath

Guest favourite

Apartment

4.87 out of 5 average rating, 261 reviews

Oceanfront Condo. Pool & Spa, 1 Br.

MAALAEA OCEANFRONT. Oceanfront lawn, panoramic views, full kitchen, washer/dryer, granite counters, oceanfront lanai, all supplies, beach gear, quiet... with pool, jacuzzi/spa, BBQ, TempurPedic queen bed, desk, free wi-fi & parking. Nearby uninhabited 5 mile long beach walk & swim, Rooms have fans and windows /screens that allow cooling breezes along with one A/C unit Peaceful Maalaea neighborhood. Centrally located to explore Maui, 15 minutes to airport. Adults(2) only. No smoking.

Guest favourite

Apartment

4.99 out of 5 average rating, 169 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.

Guest favourite

Apartment

4.99 out of 5 average rating, 104 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and ocean front views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (unit 806) that includes two bedroom suites on the world famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent body surfing, whale watching, snorkeling, scuba diving paddle boarding and kayaking literally at your doorstep.

Guest favourite

Rental unit

4.91 out of 5 average rating, 1,019 reviews

Kula Treat - Upcountry Maui with Hot Tub!

Private, gracious apartment in desirable Upcountry Maui. Great home base for exploring, and a quiet country retreat for relaxing. Restaurants, food trucks and farmers’ markets nearby. Beaches, hiking and zipline within an easy drive. Perfectly located for Haleakalā Natʻl Park and day trips to Hana. A wonderful personal chef lives very close by. Dedicated to reducing single use plastics, we provide reusable water bottles for our guests! Fully permitted: BBMP 2015/0003 E komo mai! (Welcome)

Guest favourite

Apartment

4.99 out of 5 average rating, 170 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.

Guest favourite

Apartment

4.96 out of 5 average rating, 114 reviews

A.R.A Retreats: Big Blue Pacific

Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing 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 and when the sun goes down, watch your favorite shows on on our smart tvs!

Guest favourite

Apartment

4.94 out of 5 average rating, 104 reviews

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

Guest favourite

Apartment

4.98 out of 5 average rating, 117 reviews

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.