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Villas Wailea

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26 villas

Wailea Orchid Villa - Panoramic Views! 3 Bd/3 Ba

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 8

“Wonderful stay in the Penthouse Villa...” Service: 5 Stars - The owner was very prompt in replying to email with questions, concerns. Concierge and front desk staff were courteous and very helpful. The bellman/staff even brought all of our luggage (6+ pieces) to our Villa and even parked both of our rental cars. Home: 5 Stars -Villa was immaculate! Master bedroom was gorgeous and the other guest rooms were beautiful and spacious as well. Open floor plan is great for entertaining and views from living room and lanai were breathtaking. Location: 5 Stars - just a short leisurely walk to the beach, adult-only pool and you can access the kiddie pool directly from the garage. Amenities were great - housekeeping promptly replaced shampoo and toilet paper. The Penthouse Villa offers guests a private elevator with key card access. Liked the views and proximity to beach, pools, shops the best.

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$1,457

New Listing! Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

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$851

Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

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$794

Aqua Lani J305 Wailea Beach Villas

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

“Beautiful condo in Wailea!” A wonderful condo with 3 bedrooms & 3 bathrooms for six adults that was decorated with a modern touch & clean facilities. The beach is walking distance & the private pool very relaxing (separate kids pool area); didn't take advantage of the wonderful Grand Wailea facilities next door which was accessible with the rental. Would come back in a heart beat & we thoroughly enjoyed my birthday! It was a little pricey but so worth it if you anticipate the cost if three hotel rooms at a five star hotel for 5 nights!

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$993

Grand Seascape K407 Wailea Beach Villas

Wailea villa

3 bedrooms / 2 bathrooms / sleeps 6

“Comfortable” Great location which is why I rent here, lovely interior, very well equipped, great service from everyone

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$993

Bella Luna D302 Wailea Beach Villas

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 6

“Simply Divine in Wailea” Our family of 6, 2 teen boys and 2 teen girls, had the pleasure of staying at Bella Luna in March. It was even better than the pictures. Sure it was a splurge, but there is simply no better accommodations to be had in the Wailea area. The unit was so complete and so well stocked that there was not one single thing we could think of that wasn't already there. The furnishings were spectacular, the view from the lanai was breathtaking, and the sliding glass walls allowed us to enjoy the open air all the time. The appliances, electronics, were all top notch, as were the cookware and dishes. I was impressed too with the management company, Tropical Villa Vacations. They were really on top of everything to make sure our trip was special. We will definitely go back to Wailea and stay in this unit again. I wouldn't want to stay anywhere else!

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$2,788

Sunny Surf E301 at Makena Surf

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

“Just Wonderful!” We had a wonderful time in the Makena Surf unit E301. Everything is top notch and the best equipped vacation unit we've seen. I am sure we will be back! Catherine abercrombie, Munich Germany

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$993

Azure Azul M212 at Wailea Beach Villas

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

“This was the perfect vacation rental.” This was a beautifully appointed rental in a wonderful location. For a family, this is fantastic as the Wailea Beach Villas are right on the beach and next door to a great shopping center with restaurants. The condo was in excellent condition and had a nice view. Because it is a corner unit, there is a large balcony which was a highlight for us. We enjoyed sitting on the balcony watching the sunset. Simply heavenly. I cannot wait to return.

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$993

Amazing Wailea Surf Villa at Wailea Beach Villas

Wailea villa

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay in Maui.” Dear Helen and Steve, We had a wonderful time at your Wailea Beach Villa condo. This was our second stay (first was in 2010) and we had an even better trip this time having been more familiar with the area. The beaches all along south Maui are so nice. Especially south past Wailea where there are less crowds. The snorkeling is pretty good too. The condo was the perfect size for our family of 4 plus our mother-in-law. The kitchen was well stocked with all the amenities we could think of. The kids even baked cupcakes one afternoon. The staff was very friendly and helpful. If you are considering staying at this property, you won't be disappointed. There is a lot of room, Helen is easy to work with, the beds are super comfortable and the kitchen has top of the line appliances. And you won't have to deal with the typical crowds of the resorts next door.

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$1,132

Mer Et Soleil K408 Wailea Beach Villas

Wailea villa

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful Villa Complex w/ Great Service” The Wailea Beach Villas are a wonderful complex. They are first rate on all dimensions. The villas themselves are the best in Wailea. The beach and pool have great service while also being quiet without large crowds and confusion of the nearby resorts. The concierge of Tropical Villa Vacations was one of the best and most accommodating we have ever experienced!

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$2,190

Floral Gardens Villa G102 Wailea Beach Villas

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 6

“Total luxury - we would definitely stay here again!” The villa itself (G102) was perfect. The finishings and furnishings are top quality. Much better than staying at one of the hotels. This villa is so spacious with the grass area and plunge pool. The beds are amazing!! Tropical villa vacations staff were so helpful and friendly, extremely professional. We would definitely recommend this villa.

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$1,691

Orient Pacific Suite J505 at Wailea Beach Villas

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

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$1,292

Sea Breeze Suite J405 at Wailea Beach Villas

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

“Luxurious” This villa is the most luxurious, well-equiped, and superbly located villas/hotels that we have stayed in in the Wailea area. The views from the penthouse building at WBV are amazing. You can whale watch, checkout the beach conditions, and watch the sun set from the lanai. The penthouses are also extremely close to the Shops at Wailea, so you can easily pop out for a morning coffee or to pickup a boogie board. The Sea Breeze Suite at WBV is beautifully appointed and expertly managed by Tropical Villa Vacations. The online pictures of the suite are accurate, but still don't convey how wonderful and calming this unit is. The kitchen has absolutely everything you need. Need a juicer? They have it. Like Nespresso coffee? They have it. Want to roast a chicken on the grill using a rotisserie? You can do that. Of course, since Wbv's are so centrally located, you can also go out for every meal as well. The best part about this villa (and WBV) is that everything is included. There are no additional charges for beach lounge chair & umbrella setup/use, parking, internet access, or resort fees. Yet, you still feel like you are getting the service and attention that you would get at one of the premier resorts in the area. We were able to get beach and pool-side chairs whenever we needed to as well (not always the case at the resorts). When our vacation plans take us to Maui, we will be staying at the Wailea Beach Villas. I highly recommend staying here.

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$1,192

Sandy Surf K508 at Wailea Beach Villas

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

“Beautiful condo, fabulous vacation” We had a blast on our first trip to Hawaii. The condo was spectacular. We had plenty of rooms and every possible amenity. I would highly recommend the condo we stayed in. Wailea Beach Villas is in a beautiful beach area and is much quieter than the Grand Wailea and Four Seasons next door. We did walk on the path to the other hotels for some drinks and meals. Every time we did, we were glad to get back to our more peaceful surroundings. Heads up, K508 gets a lot of noise from the kids' pool below, so if you think that will bother you, you my want to pick a different unit. Another cool bonus to the villas is that you literally walk out of the complex and out a gate into the the shops which was a big benefit for us. The shops have a couple of markets, several restaurants, souvenir shops, ice cream parlor and upscale stores. We have three teenagers so they enjoyed the shops. We would return for sure. We rented through Tropical Villa Vacations and would recommend them in a heart beat. They are really helpful and knowledgeable and go out of their way to assist with any activities and dining arrangements. We had Chef Robert of the Lahaina Catering Company cook two dinners for us and they were the highlight of our vacation. We highly recommend him. His wife and sister came to help him prep and serve and they were all delightful.

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$1,392

Blue Horizons K308 Wailea Beach Villas

Wailea villa

4 bedrooms / 3 bathrooms / sleeps 8

“It could not have been better.” From the minute we pulled up to the door in our car to the minute we left, everything was absolutely first rate. We so appreciated the gentleman who hauled all of our groceries from the car to our room when we were so tired. Questions asked were promptly answered. The condo itself was amazing. It was beautifully decorated and so well stocked. We really enjoyed the lanai where we ate most of our meals and enjoyed the sunsets. And an elevator right to our room--Wow! We also loved the idea of an adult pool with the furnished towels and ice water. Also loved the walk to the pool to enjoy the beautiful grounds and the sound of the running water. The location was ideal. Next to the Mall and restaurants. I think the thing we all enjoyed the most was the condo itself. So beautiful! There was nothing we did not like. The kids all said it was the best vacation they've ever had--it can't get better than that. Thank you, LaVon

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$3,242

Golden Mandarin D102 Wailea Beach Villas

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 6

“A terrific experience.” The location and unit were perfect (except for the large sliding doors which never closed well.) We had little contact with your staff but what we had was great.

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$2,190

Aloha Kai Suite at Wailea Beach Villas PH 205

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 8

“Best Vacation” My family and I truly enjoyed loved our stay at Aloha Kai Suite and the Wailea Beach Villas. Beautifully decorated, clean, kitchen had everything you needed, and of course the view was amazing. We loved being so close the sandy beach, the two pools, and close to the shops and restaurants at Wailea (especially the ice cream shop which they visited nightly). The staff at WBV was outstanding, very friendly and there if we needed anything from reservations to beach chairs! Susan the owner of Suite J205 was very prompt to answer any questions I had prior to booking our vacation and before our arrival. I would definitely book this unit again for our next trip to Maui!

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$1,251

Poolside Bungalow 2bed/2bath, w/ Pool & Hot Tub- Steps To Beach

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 18 minutes

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$621

Wailea Inn Maui

Wailea villa

14 bedrooms / 14 bathrooms / sleeps 34

Responds fast! avg. 2 hours 18 minutes

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$3,481

Luxury 2 bedroom Hideaway near the beach

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 18 minutes

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$621

Luxury 4 bedroom Penthouse w/ Pool & Hot Tub- Steps To Beach

Wailea villa

6 bedrooms / 6 bathrooms / sleeps 16

Responds fast! avg. 2 hours 18 minutes

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Price per night from

$1,808

Great rentals within 20 miles that match your search

Ocean Bliss Beachfront Home

Kihei villa

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$2,963

Blue Sky Villa Maui

Lahaina villa

5 bedrooms / 6 bathrooms / sleeps 11

Responds fast! avg. 3 hours 23 minutes

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Price per night from

$4,347

Modern Maui I404 at Wailea Beach Villas

Kihei villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$993

SeaSpirit Villa 811 at Andaz Maui at Wailea Resort

Kihei villa

3 bedrooms / 4 bathrooms / sleeps 6

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$3,242

Wailea Inn Maui

Kihei villa

14 bedrooms / 11 bathrooms / sleeps 32

“Maui with a Twist!” What a fabulous time we had! Everyone's dream honeymoon, a week on Maui! I'm so glad that we stayed at Hale Lele Villa instead of a hotel full of people. We got to relax in luxury, open windows to hear the ocean and we had absolute peace and seclusion when we wanted it. The house is magnificent, the views are amazing and the beach is right across the street. Scarlett made sure that we were welcomed in true Hawaiian style, and made sure we had a wealth of information available about the island. We rented a Jeep and drove around the entire island, knowing that each night we'd come back and relax in our spacious home for the week! We couldn't have asked for a more perfect honeymoon! Thank you Scarlett! I wouldn't want to stay any where else! If you were bringing a family, this is definitely a perfect spot. The kids can enjoy the pool while you unwind every evening!

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Price per night from

$3,198

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