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Villas in Wailea and Condos - Holiday Lettings - Holiday Rentals Wailea

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1,035 Holiday homes

Cottage rental in Wailea

Wailea cottage

1 bedroom / 2 bathrooms / sleeps 3

37

Responds fast! avg. 59 minutes

from £232 / night

£1,620 / week

Apartment rental in Wailea with shared pool, golf nearby

Wailea apartment

3 bedrooms / 2 bathrooms / sleeps 6

12

Responds fast! avg. 2 hours 53 minutes

from £279 / night

£1,952 / week

Holiday villa in Wailea

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 8

“Great experience in Wailea” We had a great time! The condo was perfect - nicely furnished, beautiful ocean views and all the amenities provided! Very upscale lodgings and grounds. We had a great time walking to the beach, snorkeling, and dining at all the nearby restaurants. We look forward to coming back soon!

6

Responds fast! avg. 58 minutes

from £1,107 / night

£7,744 / week

Wailea holiday condo rental

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

2

Responds fast! avg. 3 hours 43 minutes

from £507 / night

£3,549 / week

Holiday apartment in Wailea

Wailea apartment

2 bedrooms / 3 bathrooms / sleeps 8

1

Responds fast! avg. 3 hours 47 minutes

from £189 / night

£1,318 - £1,713 / week

Holiday villa with golf nearby in Wailea

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

1

Responds fast! avg. 2 hours 33 minutes

from £654 / night

£4,579 / week

Wailea holiday condo rental

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

from £306 / night

£1,883 / week

Holiday condo rental

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

9

Responds fast! avg. 3 hours 18 minutes

from £180 / night

£1,259 / week

Condo rental in Wailea with shared pool, golf nearby

Wailea condo

1 bedroom / 2 bathrooms / sleeps 4

19

Responds fast! avg. 1 hour 48 minutes

from £172 / night

£1,200 / week

Holiday apartment with shared pool, golf nearby in Wailea

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

9

Responds fast! avg. 3 hours 11 minutes

from £156 / night

£1,091 - £1,284 / week

Villa rental in Wailea with shared pool

Wailea villa

3 bedrooms / 4 bathrooms / sleeps 8

1

Responds fast! avg. 2 hours 33 minutes

from £702 / night

£4,909 / week

Wailea holiday home rental

Wailea house

3 bedrooms / 4 bathrooms / sleeps 6

2

from £1,123 / night

£7,860 / week

Holiday condo accommodation

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

from £306 / night

£2,141 / week

Wailea holiday apartment rental

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 5

from £330 / night

£2,305 / week

Holiday apartment with golf nearby in Wailea

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

7

from £458 / night

£3,206 / week

Wailea holiday apartment rental

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

6

from £201 / night

£1,403 / week

Apartment rental in Wailea

Wailea apartment

2 bedrooms / / sleeps 6

from £337 / night

£2,354 / week

Wailea holiday apartment rental

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 4

from £442 / night

£3,094 / week

Holiday apartment with golf nearby in Wailea

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Awesome Location and excellent cutsomer service” My wife and I go to Maui usually about once a year and stay in Wailea. This was our first time using ali'i resorts and they were awesome. The customer service was great from my initial contact, reservation and continued stay in Maui. We will definately use ali'i resorts for our future reservations.

7

from £257 / night

£1,798 / week

Holiday apartment with shared pool in Wailea

Wailea apartment

1 bedroom / 1 bathroom / sleeps 4

1

from £207 / night

£1,377 / week

Holiday apartment in Wailea

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“Beautiful Condo!!!” We stayed at Lawrence's condo from august 3 to 8, 2013. The condo is nestled in Wailea, which is a very safe, clean, and affluent area of Maui. The unit is immaculate and newly renovated. Lawrence also provided us with everything we needed to make our stay a very pleasant one (just check in first and see what Lawrence does not have before going out and buying it). The property also has a nice pool in case you don't feel like dealing with sand from the beach. Our friends were so jealous of us and it felt great...haha. Lawrence is very easy to work with and he replies to any questions you have right away. My wife and I plan on returning very soon!

19

from £254 / night

£1,775 / week

Wailea holiday apartment rental

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

1

from £322 / night

£2,248 / week

Holiday apartment with golf nearby in Wailea

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 5

1

from £153 / night

£1,065 / week

Holiday apartment rental

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

1

from £442 / night

£3,094 / week

Holiday apartment with golf nearby in Wailea

Wailea apartment

3 bedrooms / 2 bathrooms / sleeps 6

“I all I have to say is perfect!!” We loved this condo. It was perfect for our family and made us feel like a home away from home. It was huge and right on the golf course. Just minutes from the beach and shopping. The pool area was perfect. I think we BBQ almost every night we were there. We got married at secret beach which made this condo the perfect location.We couldnt have asked for anything better. We had a problem with the toilet and ali'i resorts sent someone over immediately to get it fixed. We will definitely stay there again :)

13

from £177 / night

£1,234 / week

Holiday apartment with shared pool, golf nearby in Wailea

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 2

“paradise found!” This is a beautiful condo, superbly out-fitted with everything you could possibly need, and is in a fantastic location within Ekahi village, very close to the pool, and yet on the quiet side - we were never bothered by noise. The lanai view (above) is perfect, and although warm during the day, the a/C works great and there are fans on the lanai as well as in each room. We always ate outside. Loved every minute of this place!

37

from £318 / night

£2,160 - £3,176 / week

Holiday apartment with golf nearby in Wailea

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

1

from £120 / night

£840 / week

Holiday apartment with golf nearby in Wailea

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great week relaxing in comfort and watching the sunset over the” This is the second time we have relied on ali'i Resorts to find us the perfect rental for our annual Thanksgiving trip to Maui. Ali'i staff helped me pick this Unit, communicated with me throughout the months, greeted us warmly and the Unit was spotless and comfortable. We were easy walking distance to the beach and the putting green and tennis courts were across from our Unit. The kitchen and bathrooms had been updated and the beds and living room furniture were very comfortable. The lanai was generous and afforded a great view of the sunset. We will definitely be back next year.

17

from £273 / night

£1,910 / week

Wailea holiday apartment rental

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

from £515 / night

£3,601 / week

Apartment rental in Wailea with shared pool

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“We love this Condo!!” We recently stayed in Ekahi 28D for about 9 days. We have 2 young children (ages 5 and 8) and we had a wonderful time! Excellent access to the beach and pools, close to restaurants and other activities we participated in. The view is amazing and the condo is beautifully remodeled and looks fantastic!! We loved being able to head out for the first half of the day and then come back and be able to relax and stay cool with the breezes coming in off the ocean. Meals out on the Lanai were a definite plus as well! I highly recommend this condo for anyone who is looking for a getaway in Maui! We will definitely be back to this condo!!

48

from £396 / night

£2,768 / week

Holiday apartment with shared pool, golf nearby in Wailea

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 5

“The place to stay in Maui!” My wife and I try to go to Maui every couple years and we always come back to this condo. We've stayed in various locations on Maui and in various condos in Wailea and this is hands down the best place to stay on the island. The beaches in the Wailea area are the best and the area is less developed/crowded than the Lahaina/Kaanapali/Kapalua area. Ekahi is our favorite development in Wailea because it fronts directly on the beach and the main pool area is fantastic. The pool is right on the beach but set back a bit so it's private. At some of the other Wailea developments, such as Elua, the pool area is open and exposed to all the traffic on the public beach walk. What's nice about this unit is it has a great location at Ekahi. The unit opens directly onto the lovely landscaped garden area and is close enough to the beach but not too close (if you stay close to the beach and pool there's more activity and noise). I can't wait to go back!

14

from £255 / night

£1,781 / week

Holiday condo in Wailea

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 4

3

from £242 / night

£1,691 / week

Holiday apartment with golf nearby in Wailea

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 5

1

from £193 / night

£1,347 / week

Wailea holiday apartment rental

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Family vacation” This was our fourth time staying in C103. We loved the fantastic view of the ocean and the beach; the well-equippe kitchen; furniture (beds, sofa, dining table) in good condition; responsiveness of ali'i Resorts (the rental company) to any requests or issues. However, we were very disappointed in the cleanliness of the condo with this visit. The were rings around both toilet bowls and mildew in the shower stalls. We had the daily maid service, but the actual cleaning was very hasty and inconsistent. The area rug in the living area was sticky and appeared to need cleaning. On a better note, when we identified these issues to ali'i, they were extremely apologetic and proactive in improving things during the remainder of our stay. Despite our disappointment with the cleanliness of the condo, we still had a wonderful stay and have already booked for 2013.

21

from £402 / night

£2,812 / week

Condo accommodation in Wailea

Wailea condo

2 bedrooms / 2 bathrooms / sleeps 6

from £243 / night

£1,698 / week

Wailea holiday villa rental

Wailea villa

3 bedrooms / 3 bathrooms / sleeps 6

“Very Nice Trip” I can surely attest that you will not be unhappy with your stay in J305 and will be pleased with the resort facilities as a whole. There are always a few items that can use improvement but the nice extras and superlatives outweigh the negatives. They could use some sharper knives and I am not a big fan of electric stove tops. The grill only got marginally hot and this obviously made grilling difficult. The elevator to our unit was broken on and off our first few days on property and I would strongly recommend the use of Wailea Beach Villas own concierge Tracy, in lieu of using the concierge assigned to you by Tropical Villa Vacations. Tracy is outstanding. Overall we had a lovely vacation and would certainly visit again and be happy to book through Tropical Villa Vacations.

8

from £1,043 / night

£7,297 / week

Holiday apartment with golf nearby in Wailea

Wailea apartment

1 bedroom / 2 bathrooms / sleeps 4

“Best relaxing vacation in Wailea!” All the communication prior to checking into the condo was excellent! we were greeted by Pat and she had already turned the air on and had lights on to greet us. Everything was explained very well, we had an amazing time using unit 2003 at Elua and will look forward to coming back and using your services again!

16

from £273 / night

£1,910 / week

Wailea holiday apartment rental

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 5

from £378 / night

£2,643 / week

Wailea holiday apartment rental

Wailea apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful Whale Watching Vacation” We spent 11 days in Unit #802 and experienced a fun and relaxing time on Maui. Our whale watching/snorkeling excursion, Old Lahaina Luau experience and trip to the Ocean Center were excellent. Out upcountry drive to the alii lavender Farm and Tedeschi Winery was also fun. We especially loved spending time on the nearby beaches, snorkeling along several different reef zones, kayaking with sea turtles and whales offshore of the Marriott resort,hiking in the lava field at the end of the road, and walking to dinner at the Shops at Wailea. We can't wait to return! We feel fortunate to have found the perfect Maui vacation spot at Wailea Village. This convenient location allowed us to easily participate in all the activities we had planned. Our unit had an ocean view where we could sit on our lanai each evening to watch the sunset. We also ate breakfast here and saw whales spouting, breeching, and cruising in the ocean every day. Having a washer/dryer to use made our trip even more pleasant as did the fully functional kitchen. We much prefer staying in a condo to a hotel room!

7

from £273 / night

£1,910 / week

Apartment rental in Wailea with golf nearby

Wailea apartment

3 bedrooms / 3 bathrooms / sleeps 8

“Amazing location, beautiful condo.” This condo is situated close to the beach and within walking distance of all the big hotels/restaurants/shops etc. It is beautifully decorated, with plenty of space for a family of 6. The swimming pools at Elua Village aren't great compared to the hotels in this area, but the main attraction here is the beach - which is spectacular. We enjoyed watching the sunset each night from our Lanai. We rented through a'li Resorts and they were fantastic. Check in was easy, we had daily housekeeping and free concierge service. They were very attentive -- when we needed more propane for the BBQ grill, they had it delivered within a couple of hours.

12

from £1,144 / night

£8,007 / week

Viewing 40 of 1,035
rentals in Wailea

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Wailea holidays

Famous for its five half-moon shaped beaches and world-class golf courses, Wailea is five times the size of Honolulu’s Waikiki with unmatched Pacific Ocean views. For a luxurious Hawaiian holiday in a very sought-after location, visit Holiday Lettings where you will find a Wailea holiday rental to suit all your needs.

About Wailea

Wailea is located on the south-western part of Hawaiian Island of Maui, just 14 miles from Kahului Airport.

Meticulously laid out over 1,500 acres of lush tropical vegetation, the beach at Wailea is one of the most visited on Maui. The popularity of the beach is partly due to the area’s luxurious oceanfront resorts and spas, as well as its legendary year-round average temperature of 82 degrees!

Even the shopping at Wailea has an up-market feel with Gucci, Louis Vuitton, Prada and Tiffany & Co all represented next to surfing boutiques such as Quicksilver, Rip Curl and the Honolulu Surfing Company.

When it comes to fine dining, you will be spoilt for choice with American, international and Hawaiian specialities all available.

Top Wailea events include the February Whale Week and the Maui Film Festival. See if you can catch one during your stay!

What to do

Avid golfers flock to Wailea just to play the Gold Course (one of the top golfing destinations in the country!). Robert Trent Jones II designed championship course that takes advantage of the natural surroundings, while incorporating stunning ocean views from every tee. A true thinking man’s course, and considered one of the best designed courses in the world.

Hawaii is, of course, all about surfing and Maui has its fair share of top spots where the pros come to catch big winter waves. But on the south of the island, the waves are around three feet in height, making them perfect for beginners.

Go hiking in the Haleakala National Park and climb to the top of the world’s largest dormant volcano, Haleakala, where you will be rewarded with fantastic views of the island.

Top Wailea travel tips

With almost perfect weather all year round, there is no bad time to visit Wailea.

For beach attire, avoid the fancy stores and ask the locals where they go shopping, instead. Consider buying a snorkel, mask, and fins as it can actually work out cheaper than renting.

Hawaii is a no-brainer for a tropical beach holiday, but with so many great amenities, Wailea truly is a world-class destination. To find your slice of paradise, Holiday Lettings has dozens of Wailea holiday rentals to suit all budgets.

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