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Wailea Luxury Rentals

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433 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
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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
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Owner Direct *Read Our Guest Reviews* Elua Village 701, Luxury 2BR, Ocean View
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury 2br/2ba Panoramic Ocean And White Water Views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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TOTAL REMODEL – REVIEWS ARE GREAT AND NOW HERE ARE THE PICTURES
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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BEACH LUX VILLA with AWESOME VIEW - Click on video for a tour!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Wow !! What a Great View!!--GREAT REVIEWS !
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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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
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Save time - get the best Wailea rentals sent straight to your email!
Perfect Couple Retreat! Enjoy Sweeping Ocean Views High End Top Floor Remodel
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Dec 7-16 2022 available Beautiful oceanview Palms at Wailea 503
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Ocean View Wailea Condo
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Wailea Ekahi Ocean View 50A
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Just Steps to Kamaole III Beach!!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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Maui Breeze Retreat....top row views! Ask about GW passes for 12/27-1/3 booking!
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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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
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Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Golf Course. Sleeps 4.
Rental Home
1 bedroom
2 bathrooms
Sleeps 4
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~ This is Wailea Living ~
Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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5D - One of the closest to the Beach, Recently remodeled and very well equipped.
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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On Wailea Blue Golf Course ⛳️with Ocean View. �
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Breathtaking Ocean View in Upscale Wailea
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Exclusive Listing! Gorgeous, High-end Wailea Suite!!!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Incredibly Large Palms at Wailea Polynesian Style Villa
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Newly Remodeled Spacious Ground Floor Unit -Wailea Ekahi #22B
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Grand Champions 120 Ocean View 2-Bedroom Condo. Bright and Very Clean.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Listing! Fully Renovated! STUNNING VIEWS!! Elua 2305
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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DEC 4-11, JAN & FEB OPENINGS Gorgeous Palms at Wailea, Updated, Full AC, 1st Fl.
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Ocean View, Steps away from the pool
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Elua Village - Beach Front Residential Resort- Luxury 2 bdrm - Great Ocean Views
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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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
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Magnificent Panoramic Views!! Gorgeous Completely Remodeled Private End Unit!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wailea Ekolu 304 - Luxurious Front-Row Unit with Amazing Ocean & Golf Views
Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Amazing Oceanview! Wailea Ekolu 1BR/2BA - Walk to Golf!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Luxurious, Fully Updated 2nd Floor 2Bd/2Ba Paradise with ultra quiet A/C
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2-4)
Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Fabulous Ocean & Fairway Views! Top Floor 3 BR! Grand Champions 170
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful December Escape!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Ocean View Studio
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Remodeled in 2021 - LAST MINUTE DEAL! Wailea Elua #2002 Ocean View Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quiet, Spacious1 Bdrm/2 Bath at Palms at Wailea!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Wailea Ekahi 51F Oceanview - Walk to Beach
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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STOP! LOOK NO FURTHER! Palms at Wailea #1503 Ocean View Best Location!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Ocean and Golf Course View 3 Bedroom - Close to the pool!
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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OMGosh! Incredible Value! Ekahi 47E!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Save $$$ - Best Value in Wailea
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Palms at Wailea 902 - Luxuriously Decorated, Spacious, and Very Private & Quiet
Rental Home
1 bedroom
2 bathrooms
Sleeps 4
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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.
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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.
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.