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Wailea Rentals with Pools

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392 rentals in Wailea.
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Wailea Ekahi Ocean View 50A
1 bedroom
2 bathrooms
Sleeps 4
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New Listing! Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
3 bedrooms
4 bathrooms
Sleeps 8
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Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Golf Course. Sleeps 4.
1 bedroom
2 bathrooms
Sleeps 4
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Beautiful Wailea Condo Wailea Ekolu # 401
2 bedrooms
2 bathrooms
Sleeps 6
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Stunning Beach Front Condo Makena Surf Resort # E-204
2 bedrooms
2 bathrooms
Sleeps 6
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Elua Village # 701 - Luxury 2b/2b with Ocean View, and Newly Remodeled!
2 bedrooms
2 bathrooms
Sleeps 4
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Wailea Ekahi Village 29F Ocean Front
1 bedroom
2 bathrooms
Sleeps 4
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Beautiful Oceanfront Ground Floor Unit MAKENA SURF RESORT, #G-101
2 bedrooms
2 bathrooms
Sleeps 6
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One-of-a-Kind Maui Getaway!
4 bedrooms
4 bathrooms
Sleeps 10
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Prime Wailea 2 BDRM Condo Wailea Elua Village # 801
2 bedrooms
2 bathrooms
Sleeps 6
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Best Kihei Location; Oceanfront with Stunning Views; Spacious 2BR on the Beach!
2 bedrooms
2 bathrooms
Sleeps 6
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Lovely Ground Floor 2 BDRM Condo Wailea Elua Village # 105
2 bedrooms
2 bathrooms
Sleeps 6
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WAILEA ELUA, #0702
2 bedrooms
0 bathrooms
Sleeps 6
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Sweeping Ocean Views; Private High End Condo!
1 bedroom
2 bathrooms
Sleeps 4
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Aloha Kai Suite at Wailea Beach Villas PH 205
3 bedrooms
3 bathrooms
Sleeps 8
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WOW ! WHAT A GREAT VIEW ! ---Great Reviews !
2 bedrooms
2 bathrooms
Sleeps 6
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OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA
1 bedroom
2 bathrooms
Sleeps 3
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Wailea Ekahi 7G Luxury Ocean Front S Maui Condo
1 bedroom
2 bathrooms
Sleeps 2
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Wailea Ekahi 11f: Ocean View/Remodel 2 BR Condo
2 bedrooms
2 bathrooms
Sleeps 4
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Amazing Wailea Surf Villa at Wailea Beach Villas
2 bedrooms
2 bathrooms
Sleeps 6
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NEW REMODEL 2020-65”SONY 4K UHD LED LCD TV & BOSE SURROUND SOUND- GORGEOUS GEM
1 bedroom
2 bathrooms
Sleeps 4
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The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
2 bedrooms
2 bathrooms
Sleeps 6
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Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D
1 bedroom
2 bathrooms
Sleeps 2
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Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4
2 bedrooms
2 bathrooms
Sleeps 4
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Luxurious 2.5 Bedroom - Flexible Rebooking if Needed!
2 bedrooms
2 bathrooms
Sleeps 6
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SPECIAL $300/nt 1/30-5/18/21 Wailea Ekahi33A LuxResort, Beach-3 min walk,Remodel
1 bedroom
2 bathrooms
Sleeps 5
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Ekahi 40A - Walk to the Beach from a Quiet Private Garden Oasis
1 bedroom
2 bathrooms
Sleeps 4
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Wailea Luxurious Beachfront 2br,2ba on Polo Beach Unit #408
2 bedrooms
2 bathrooms
Sleeps 4
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Wow - Incredible Ocean Views - Beautifully Remodeled
1 bedroom
2 bathrooms
Sleeps 2
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Enjoy the Amazing View and have a Mai Tai too!
1 bedroom
2 bathrooms
Sleeps 4
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Stunning Ocean/Sunset View in Gorgeous, Updated Wailea Grand Champions 166
2 bedrooms
2 bathrooms
Sleeps 6
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Gorgeous 2 Bdrm Ocean Front - Makena Surf Resort #G-201
2 bedrooms
2 bathrooms
Sleeps 6
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Wailea, Oceanfront, Luxury, Polo Beach Club Condo #403
2 bedrooms
2 bathrooms
Sleeps 5
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Palms at Wailea #1101 Great Ocean Views! Large Sun Deck! 2/2 Great Rates!
2 bedrooms
2 bathrooms
Sleeps 6
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On the beach, totally renovated, 5 star everything
2 bedrooms
2 bathrooms
Sleeps 5
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Updated Spacious 3 Bdrm. Wailea Ocean View Condo
3 bedrooms
2 bathrooms
Sleeps 6
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Grand Champions #48: Stunning 180 Degree Ocean Views. Top Floor Paradise Home
2 bedrooms
2 bathrooms
Sleeps 6
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5D - One of the closest to the Beach, Recently remodeled and very well equipped.
1 bedroom
2 bathrooms
Sleeps 5
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Amazing view, Closest to the beach, Wailea Ekahi, Unit 20i.
1 bedroom
2 bathrooms
Sleeps 4
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Largest Two Bedroom/ Two Bath in the Village! Sleeps Eight. Close to the Beach.
2 bedrooms
2 bathrooms
Sleeps 8
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Privacy in Paradise! Ocean View 3 Bedrooms,. Completely Remodeled.
3 bedrooms
2 bathrooms
Sleeps 5
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Luxury at its Best W/ Big Ocean Views!!
2 bedrooms
2 bathrooms
Sleeps 4
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The Perfect Location for a Relaxing Getaway
1 bedroom
2 bathrooms
Sleeps 4
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Luxury, Fully Remodeled! Ocean & Golf Views! NEW Split AC & Local Gym Pass Incl
2 bedrooms
2 bathrooms
Sleeps 4
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1 BR Treetop Luxury from $150/nt
1 bedroom
1 bathroom
Sleeps 2
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Gorgeous Luxury Ocean View Top Floor Corner Unit w/A/C, Pool, Free Parking/Wifi
1 bedroom
2 bathrooms
Sleeps 4
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14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
1 bedroom
2 bathrooms
Sleeps 3
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Hawaiian Escape -Blue Golf Course
1 bedroom
2 bathrooms
Sleeps 4
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Mer Et Soleil K408 Wailea Beach Villas
4 bedrooms
3 bathrooms
Sleeps 8
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New Contemporary Elegant: 4 Bd, 3Ba, 3811S.F. & Office: Wailea Beach Villas 208.
4 bedrooms
3 bathrooms
Sleeps 8
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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.