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Wailea Rentals with Pools

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306 rentals in Wailea.
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Our living room includes a beautiful lydesigned koa entertainment system with plasma tv and stereo.
Granite counter tops and high end kitchen appliances
Front entrance with private 2nd bedroom suite entrance
Wailea Ekahi 11f: Ocean View/Remodel 2 BR Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Updated lanai with Haleakala and small ocean view
NEW REMODEL 2020-65”SONY 4K UHD LED LCD TV & BOSE SURROUND SOUND- GORGEOUS GEM
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Stunning Remodel, Fantastic Lower Village Location, 1 Minute to Pool & Beach! 6C
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps, All pools
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The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Hula On In to Beach House Chic Style, Click on Video tour!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Ocean View, Close to Beach&Pool Sleeps 10
Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach-3 min walk, Remodeled
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Wailea Ekahi 40A - Walk to the Beach from a Quiet Private Garden Oasis
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Wailea Ekahi Ocean View 50A
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Stunning Ocean/Sunset View in Gorgeous, Updated Wailea Grand Champions 166
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Modern Spacious Beachfront Luxury rental in Ekahi Village - Apartment 39F
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Amazing view, Closest to the beach, Wailea Ekahi Unit 20i
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Newly Remodeled Spacious Ground Floor Unit -Wailea Ekahi #22B
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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5 Star Ocean View, Beach House Chic, Click on Video tour!
Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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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
Match: Sleeps, All pools
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Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Enjoy Beautiful Sunsets with this Ocean View!!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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GORGEOUS Palms at Wailea 207, 1st Fl, Updated, Full AC, Pool, Walk to beach....
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century Modern
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, All pools
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Grand Champions #48: Stunning 180 Degree Ocean Views. Top Floor Paradise Home
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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5 Star Reviews! Guests say: 'Location, Location & Everything you could ask for'!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Ekahi 36a, 1BR 2BA, Sleeps 4, Stunning Renovation - Canadian discounts available
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Wailea Ekolu #105 Partial Ocean view, Sleeps 4
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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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
Match: Sleeps, All pools
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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
Match: Sleeps, All pools
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COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Beautiful Ocean /Golf Course Views, Remodeled, Vaulted Ceiling
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, All pools
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Beautiful Ocean View Studio
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Availability in this Quiet, Spacious 1 Bdrm/2 Bath!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps, All pools
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Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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NEW RENOVATION WITH FULL OCEAN VIEW WAILEA
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps, All pools
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Million Dollar Ocean & Golf Course Views from this beautiful 2 bed 2 bath Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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OMGosh! Incredible Value! Ekahi 47E!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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SPECTACULAR �OCEAN & � SUNSET VIEWS, 3br/2ba Villa in Wailea
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Prime Oceanfront 3Bd/3Ba Condo Wailea Elua #1305
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Wailea Sunset View. Modern, Relaxing, Quiet & Clean Wailea Grand Champions 174
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Fantastic Beach & Tropical Gardens
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Treetop Studio from $130/night
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Upgraded Unit w/ Beautiful Ocean Views Makena Surf Resort # C-103
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Tropical Paradise- Maui Vista’s biggest 2B/2 bath
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Palms at Wailea #1508, Panoramic Ocean View 2Bd/2Ba, Sleeps 6, Great Rates!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Grand Seascape K407 Wailea Beach Villas
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Fantastic Wailea Ekahi Beachfront Condo 45F
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, All pools
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Floral Gardens Villa G102 Wailea Beach Villas
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Maluhia at Ho'olei Grand Wailea Resort -DELUXE Ocean View with Resort Privileges
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Exquisite Remodel. Stunning Ocean Views with Beachfront Access
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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*Labor Day Special* Modern and Luxurious Beachfront Property
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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SPECIAL $230 9/18-25 Ekahi33A 1bd/2bth, Luxury Condo, Beach 3 min walk,Remodel
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Wailea Vacation Rentals
Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.
More
Wailea Vacation Rentals
Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.
A Wailea Vacation
No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.
Family-Friendly Wailea
From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.