Villa vacation rentals in Wailea, Wailea-Makena

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Top-rated villa rentals in Wailea, Wailea-Makena

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An open living area with large glass doors showcases a scenic view of the sea and landscape. A kitchen island with a sink features a stylish countertop. Comfortable seating arrangements are placed throughout, enhancing the casual ambiance of the space.

Villa in Lahaina

5 out of 5 average rating, 9 reviews

OPEN & Reduced 4/8 - 4/21 ~ Paradise for 2

Aloha! Welcome to Hale 'Ikena Makai, pronounced Ha-lay e-ken-na ma-ki, 'Home with a View of the Sea'. This property is the original member of Platinum Maui Vacations. We include: ~Resort Shuttle ~Secured wifi / internet ~Central AC (new 2020) ~Quality Cal King bed with Clean & Fresh linens over hypoallergenic covers ~Tommy Bahama beach chairs ~Big fluffy beach towels ~Ice cooler ~Boogie boards ~24/7 on call, on island contact ~Dedicated & covered parking NO DISAPPOINTMENTS HERE ~ Always 5 Stars

Superhost

The living area features comfortable seating with a sofa and armchair. A wooden coffee table is centered in front of the sofa. Natural light enters through large glass doors that lead to an outdoor patio, creating an inviting space for relaxation.

Villa in Lahaina

4.94 out of 5 average rating, 35 reviews

Ground floor, ocean view, private, Kapalua Ridge

Welcome to Kapalua Ridge Villa 612. This large 1 bedroom, 2 bathroom 1125 sq ft condo features an open floor plan with a large private shaded lanai. Admire Honolulu Bay, sunsets, whale watching, sailboats, & more. This condo has ocean views from the lanai, living area, dining area, & kitchen. The unit can comfortably accommodate 4 people. The pool is a few steps away & there is a walk path that leads you all the way down to the resorts/beach. Kapalua Ridge Villas is coastal Luxury at it's best.

Guest favorite

A coastal view features tall palm trees swaying gently against a clear blue sky. The sandy beach stretches along the shoreline, leading to calm turquoise waters. In the distance, a glimpse of a distant landmass is visible, adding to the serene atmosphere.

Villa in Wailea-Makena

4.96 out of 5 average rating, 94 reviews

Luxury at it's Finest, Truly a Home away from Home

Remodeled in 2020, this 2 /2 Villa is located at Grand Champion Golf & Tennis Villas in the exclusive resort destination of Wailea, Maui. We have been named a Super Hosts on Airbnb due to the great amenities, comfort, safety, cleanliness and luxurious accommodations this Villa provides. Wailea is the Gold Coast of Maui, close to pristine beaches, shopping and dining and this is a legal, exclusive vacation rental. Spacious and luxurious, feel Refreshed and Anew in your Home away from Home!

Superhost

A bright living area features a comfortable sofa with coordinating armchairs, complemented by a round wooden coffee table. Large glass doors provide an unobstructed view of the ocean and tropical landscape, allowing natural light to fill the space.

Villa in Wailea-Makena

5 out of 5 average rating, 4 reviews

Ocean Views! Remodeled Redecorated Pretty & Modern

Our collection of Maui vacation residences are HOTEL-Zoned or have LEGAL short-term rental permits. Reserve with Private Paradise Villas with confidence knowing you will be luxuriating in a location legally designated for visitor accommodations and managed by our local on-island professional staff. NEW! NEW! NEW! VIEWS! VIEWS! VIEWS! Surf Song Villa 203, a newly remodeled and redecorated direct ocean view resort residence set in the beachfront and upscale Wailea Elua Village Resort, is ...

Superhost

Villa in Lahaina

4.84 out of 5 average rating, 89 reviews

Panoramic Ocean-View Villa steps from the beach!

Enjoy amazing, panoramic views in this bright and open island living area connected to an expansive lanai balcony. Great for families with a connected living and entertaining space, but also quiet and private with two bedrooms that each have their very own private patios and dual vanity bathrooms. This is a very flexible space that is ready for the vacation that you want to make of it! Kapalua has world-class beaches, beautiful landscapes, and amazing activities/amenities all around!

Guest favorite

Villa in Kapalua

4.87 out of 5 average rating, 23 reviews

Kapalua Bay Villa 12G5 By Parrish Maui

The Kapalua Bay Villas are closest to Oneloa Beach offering spacious one and two-bedroom oceanfront and ocean view villas with well-appointed kitchens, laundry and central air conditioning. Resort amenities include three pools, two tennis courts, gas BBQs and direct access to the popular Kapalua Coastal Trail. Wake up each morning to breath taking views of the Pacific from the upstairs master bedroom suite or relax on your spacious private lanai and enjoy the sounds of Maui.

Guest favorite

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. A decorative rug runs across the floor, while fresh greenery and a welcome sign add a touch of warmth. Natural light fills the space, highlighting the inviting atmosphere.

Villa in Wailuku

4.96 out of 5 average rating, 203 reviews

Luxurious Two Bedroom near I’ao Valley w/ Haleakal

Enjoy Haleakalā views from this spacious 2BR villa at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Featuring a King and Queen bed, full kitchen, spa-like bath with soaking tub, and a private deck. Walk to cafés, shops, and theaters, or take a short drive to ʻĪao Valley, beaches, and top Maui attractions. Includes modern comforts, air conditioning, parking, and an on-site infrared sauna for a relaxing retreat away from the crowds.

Top guest favorite

A private heated swimming pool is surrounded by lounge chairs and palm trees. The pool features a clear blue surface reflecting the sky, with a small set of stairs leading in from the edge. The area is landscaped with vibrant green foliage.

Villa in Lahaina

4.9 out of 5 average rating, 40 reviews

Breathtaking Kapalua Views, 3 Beds, 2 Pools, Golf

This fully-equipped, locally-owned top-floor Kapalua Ridge Villa offers breathtaking ocean views and resort amenities, with many pristine beaches nearby! Take advantage of the private pools, world-class golf courses, and fine dining, then look forward to a mesmerizing sunset over the Pacific Ocean from your secluded lanai. With everything you need for a comfortable and luxurious stay, this spacious villa is the perfect home away from home for your next adventure.

Guest favorite

The image displays a lush tropical landscape featuring a lagoon-style pool surrounded by palm trees and poolside seating. A sandy beachfront leads to tranquil ocean waters, with distant island views under a clear blue sky.

Villa in Lahaina

5 out of 5 average rating, 12 reviews

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

Submit your requested dates & I will check availability & respond if I can confirm this rental for you. 2 Bedroom Westin Nanea Ocean Villa at Kaanapali Beach on Maui Island in Hawaii; 1,260 SQ FT; SLEEPS UP TO 6 ADULTS All the luxuries & amenities of a Westin resort + comfort of a villa w/ furnished kitchen, in-room washer/dryer, private balcony. Resort activities; gym/spa; Pool. Actual villa unit is assigned at check-in and views will vary; Free self-parking

Superhost

An expansive swimming pool is surrounded by palm trees and vibrant tropical landscaping. Lounge chairs in soft pink are arranged around the pool, which features a scenic rock formation. The ocean is visible in the background, with gentle waves lapping at the shore.

Villa in Lahaina

4.92 out of 5 average rating, 24 reviews

Kaanapali Beach Club "Deluxe Ocean View"

**PLEASE ASK! We have many more weeks, dates and many GUARANTEED views!** Prices based on views, events, etc. **HOTEL TAX of approx 19.00 per night paid to resort upon check in.** Located on Maui's world famous Ka'anapali Beach. Vibrant tropical landscaping, first-rate amenities and exclusive array of leisure activities. Kaanapali Beach Club offers a one-acre swimming pool with separate kids pool, as well as calming outdoor whirlpool hot tubs. *Stock Photos

Superhost

A vibrant landscape showcases lush greenery and colorful flowering plants, leading to a spectacular view of the ocean and sandy beach. The deep blue water contrasts with the bright green and colorful foliage under a clear sky, offering an inviting tropical atmosphere.

Villa in Lahaina

4.93 out of 5 average rating, 102 reviews

Kapalua Ridge 2012- Whale Watching Ocean Views

Special Offer! Stay 7 nights or more and enjoy one night FREE, or receive $100 off stays of 5 nights or fewer. Valid for stays now through June 30, 2025. Discount applied after booking confirmation. Upon entering this one bedroom/two bath Ridge Villa at The Kapalua® Resort, it is impossible not to be taken aback by the spectacular sweeping ocean views! *Please note that the Kapalua Resort and this property were not affected by the Lahaina fires.

Superhost

A spacious outdoor area features a private pool with clear blue water, framed by stone landscaping. An arched structure offers shade near the pool, and a red bowl sculpture adds a pop of color. Lush greenery surrounds the space, enhancing the serene environment.

Villa in Lahaina

4.86 out of 5 average rating, 78 reviews

Kaanapali Fairway Villa 3BR, 3BA.

Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.