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Maui Vacation Rentals

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66 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.

Responds fast! avg. 1 hour 0 minutes

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$1,460

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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$858

Spectacular 3rd Row at Ho'olei with Ocean Views

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

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$799

Wailea Inn Maui

Kihei villa

14 bedrooms / 13 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!

Responds fast! avg. 3 hours 11 minutes

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$3,206

Ocean Bliss Beachfront Home

Kihei villa

3 bedrooms / 4 bathrooms / sleeps 6

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$2,982

Modern Maui I404 at Wailea Beach Villas

Kihei villa

3 bedrooms / 2 bathrooms / sleeps 6

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$1,495

Privately-Owned Penthouse with Ocean views in Maui

Kapalua villa

3 bedrooms / 4 bathrooms / sleeps 6

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$3,640

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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$1,595

Stunning Kapalua Golf Villa - Gourmet Kitchen - Golf & Ocean View - Lanai

Kapalua villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

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$411

Majestic Villa with Ocean and Sunset Views in Prestigious Kapalua

Lahaina villa

3 bedrooms / 2 bathrooms / sleeps 6

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$488

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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$1,350

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Price per night from

$1,042

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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$2,695

Actual Owner! 2 bedroom Villa / Oceanfront - Sleeps 8 - All dates

Lahaina villa

3 bedrooms / 3 bathrooms / sleeps 12

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$1,024

Two bedroom Marriott Maui Ocean Club Towers. Full resort access! All weeks!

Lahaina villa

2 bedrooms / 2 bathrooms / sleeps 8

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$1,014

Kapalua Bay Villas 23B-1

Lahaina villa

1 bedroom / 1 bathroom / sleeps 4

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$373

Luxurious Kapalua Golf Villa Getaway Newly Remodeled 1BR/2BA NEW Listing

Kapalua villa

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 38 minutes

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$309

4/10/2021 (7 nights) Premium 1-bedroom suite | Westin Kaanapali Resort Villas

Ka'anapali villa

1 bedroom / 1 bathroom / sleeps 5

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$482

Hale Ka'ikenanani

Kapalua villa

1 bedroom / 2 bathrooms / sleeps 4

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$228

Ocean Dreams Villa 2203 Residences, Kapalua Beach

Kapalua villa

3 bedrooms / 4 bathrooms / sleeps 8

“Heavenly” Lovely amenities in this condo...perfect location for our family's activities. Relaxing and the staff is amazing!!! We had a couple issues with the appliances and the staff was there immediately. The entire experience was perfect. The Swimming pool and the private grottos, plantings not to mention the size of it, was awesome.

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$2,495

Ocean Front at Westin Kaanapali North

Ka'anapali villa

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 35 minutes

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$1,229

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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$2,295

Westin Ka'anapali, Stunning Two Bedroom Villa, Ocean Front Resort

Ka'anapali villa

2 bedrooms / 2 bathrooms / sleeps 8

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$685

Ocean Front 2 bd/2 ba February Week Westin Ka'anapali Ocean Villas Resort North

Ka'anapali villa

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 45 minutes

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$720

Christmas 3Bdrm Beachfront Nanea Westin Kaanapali

Ka'anapali villa

3 bedrooms / 2 bathrooms / sleeps 12

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$1,024

1 bed room ocean front deluxe villa - The Westin Ka'anapali Ocean Resort North

Ka'anapali villa

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$1,343

CHRISTMAS WEEK 3 BDRM BEACHFRONT NANEA RESORT

Ka'anapali villa

3 bedrooms / 2 bathrooms / sleeps 11

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Price per night from

$1,139

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.

Responds fast! avg. 1 hour 0 minutes

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$1,140

Gorgeous Oceanfront Kaanapali Beach Club, One bedroom villa. Save thousands!

Ka'anapali villa

1 bedroom / 1 bathroom / sleeps 4

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$403

Westin Kaanapali Villas North

Ka'anapali villa

2 bedrooms / 2 bathrooms / sleeps 8

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$916

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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$1,695

Beautiful 1bed / 1 bath Villa for rent in the newest resort in Ka’anapli

Ka'anapali villa

1 bedroom / 1 bathroom / sleeps 4

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$631

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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$1,495

Kapalua Golf Villa 14T

Kapalua villa

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 59 minutes

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$373

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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$1,995

10 Days in Paradise

Ka'anapali villa

1 bedroom / 1 bathroom / sleeps 5

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$487

Hale O Mana'o Nani

Kapalua villa

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$286

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