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Wailea Villas

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423 rentals in Wailea.
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Wailea Ekolu #805 Deluxe 2Bd/2Ba, Ocean View Townhouse! Full A/C, Sleeps 4
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Grand Seascape K407 Wailea Beach Villas
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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2 Bedroom, 2 Bath Oceanview Penthouse Condo! Walk to the Beach!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
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Upgraded Unit w/ Beautiful Ocean Views Makena Surf Resort # C-103
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Beach Front Luxury Corner Unit MAKENA SURF RESORT, #E-206
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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MAKENA SURF RESORT, #C-102
Condo/Apartment
2 bedrooms
0 bathrooms
Sleeps 6
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Aloha Kai Suite at Wailea Beach Villas PH 205
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Ground Floor 1 Bed/2 bath WAILEA ELUA, #807
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
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Wailea Ekahi 11f: Ocean View/Remodel 2 BR Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Wailea Ekahi Ocean View 50A
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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NEW REMODEL 2020-65”SONY 4K UHD LED LCD TV & BOSE SURROUND SOUND- GORGEOUS GEM
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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Fantastic Private Location Super Close to Pool & Beach!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
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Amazing Wailea Surf Villa at Wailea Beach Villas
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
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Luxurious 2.5 Bedroom - Flexible Rebooking if Needed!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Panoramic Ocean View In The Heart Of Wailea On Golf Course
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Keep Calm and Hula On In to Beach House Chic Style
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Ocean View, Close to Beach&Pool Sleeps 10
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
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5 Star Reviews! Wailea Ekolu with Ocean Views & Great Location!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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Enhanced Cleaning, Big Discounts & Sweeping Ocean Views from thisTop Floor Condo
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
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Ekahi 40A - Walk to the Beach from a Quiet Private Garden Oasis
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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Enjoy the Amazing View and have a Mai Tai too!
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach-3 min walk, Remodeled
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
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Monthly Discounts through April 2021 at our beautiful Palms at Wailea 503 condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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�GEORGEOUS Wailea Retreat!�Top tier UPGRADES. Very Spacious and Peaceful!�
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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Upscale Modern & Renovated with Designer Showers 1148 sq ft with 224 sq ft lanai
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Golf Course. Sleeps 4.
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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Stunning Ocean/Sunset View in Gorgeous, Updated Wailea Grand Champions 166
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Wailea, Oceanfront, Luxury, Polo Beach Club Condo #403
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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The Perfect Location for a Relaxing Getaway
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
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WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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5 Star Ocean View Villa, Ground Floor, Beach House Chic Decor
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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New Contemporary Elegant: 4 Bd, 3Ba, 3811S.F. & Office: Wailea Beach Villas 208.
Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
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Amazing view, Closest to the beach, Wailea Ekahi, Unit 20i.
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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Luxury, Fully Remodeled! Ocean & Golf Views! NEW Split AC & Local Gym Pass Incl
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Exclusive Listing! Gorgeous, High-end Wailea Suite!!!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
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Wailea Ekolu #406 2 BD 2BA Panoramic Ocean View, Full A/C, Sleeps 4
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Modern Spacious Beachfront Luxury rental in Ekahi Village - Apartment 39F
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Summer Travel Guarantee–Cancel up to 14 days before your arrival for full refund
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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Enjoy Beautiful Sunsets with this Ocean View!!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Incredibly Large Palms at Wailea Polynesian Style Villa
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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GET-A-WAY WINTER AVAILABLE Luxury Wailea Dream Location, Full AC, BBQ and more
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Palms at Wailea #1101 Great Ocean Views! Large Sun Deck! 2/2 Great Rates!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Luxury at its Best W/ Big Ocean Views!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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5 Star Reviews! Guests say: 'Location, Location & Everything you could ask for'!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Largest Two Bedroom/ Two Bath in the Village! Sleeps Eight. Close to the Beach.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
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Ekahi 36a, 1BR 2BA, Sleeps 4, Stunning Renovation - Canadian discounts available
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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Wailea Holiday Rentals
If you're flying halfway around the world to visit Hawaii then you'll want to have a comfortable stay once you get there, and there are a huge number of holiday rental properties where you can make yourself at home completely and relax and enjoy your holiday in the volcanic island paradise. Wailea is in the south of Maui, Hawaii's second biggest island, and you will need at least a week to sample all the activities that the region has to offer. Hawaii is probably not the first place you would think of for a family friendly holiday, but with beachfront condos and villas available for less than $1,000 a week, and dozens of amazing beaches all around, Wailea is great for kids and can certainly work out as a money saving option compared to the highly expensive hotels of Wailea resort.
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Wailea Holiday Rentals
If you're flying halfway around the world to visit Hawaii then you'll want to have a comfortable stay once you get there, and there are a huge number of holiday rental properties where you can make yourself at home completely and relax and enjoy your holiday in the volcanic island paradise. Wailea is in the south of Maui, Hawaii's second biggest island, and you will need at least a week to sample all the activities that the region has to offer. Hawaii is probably not the first place you would think of for a family friendly holiday, but with beachfront condos and villas available for less than $1,000 a week, and dozens of amazing beaches all around, Wailea is great for kids and can certainly work out as a money saving option compared to the highly expensive hotels of Wailea resort.
Things to do in Wailea
Obviously you will be wanting to hit the beach in Hawaii, and there are many from which you can choose, such as Keawakapu Beach, surrounded by golf courses. If you don't want to spend all your time lying on one of the many south-facing beaches but aren't quite brave enough to go and climb a volcano, Wailea has many things to do for all ages, from playing golf and tennis to the inevitable shops and restaurants, all in an incredible Pacific climate. Wailea is fairly sparsely populated, with around 6,000 inhabitants, so you can also have a great time exploring the countryside nearby.
Renting villas and condos in Wailea
Wailea Resort is a wonderful place to visit and stay, but its planning is a bit contrived - the Wailea Community Association issue guidelines for new buildings aiming to preserve the island feel of Maui. With the additional aim of low population density, this does mean that prices even for holiday rentals may be higher than in other parts of the Hawaii island chain. But with the scary prices charged by hotels, and the extra flexibility associated with renting your own villa or condo for your family, Wailea holiday rentals still represent fantastic value for money. With air conditioning thankfully coming as virtually standard, and difficult choices of whether you'd prefer views of a volcano, a golf course, or perhaps a beach, it's an idyllic place to enjoy a great family holiday. And if you are looking for a low cost Pacific break, nothing beats buying local produce and cooking it up in your very own kitchen for the week, rather than relying on a hotel's expensive restaurants.