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Wailea Villas

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338 rentals in Wailea.
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Wailea Luxurious Beachfront  2br,2ba on Polo Beach Unit #408, vacation rental in Wailea

Wailea Luxurious Beachfront 2br,2ba on Polo Beach Unit #408

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Wailea Ekahi Ocean View 50A, vacation rental in Wailea

Wailea Ekahi Ocean View 50A

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Palms at Wailea #1101 Great Ocean Views! Large Sun Deck!  2/2 Great Rates!, vacation rental in Wailea

Palms at Wailea #1101 Great Ocean Views! Large Sun Deck! 2/2 Great Rates!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach-3 min walk, Remodeled, vacation rental in Wailea

Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach-3 min walk, Remodeled

1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Royal Mauian 411: Direct Oceanfront, Total Privacy, Best Location!! With A/C!, vacation rental in Wailea

Royal Mauian 411: Direct Oceanfront, Total Privacy, Best Location!! With A/C!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Grand Champions #48: Stunning 180 Degree Ocean Views. Top Floor Paradise Home, vacation rental in Wailea

Grand Champions #48: Stunning 180 Degree Ocean Views. Top Floor Paradise Home

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, vacation rental in Wailea

Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Elua Village # 701 - Luxury 2b/2b with Ocean View, and Newly Remodeled!, vacation rental in Wailea

Elua Village # 701 - Luxury 2b/2b with Ocean View, and Newly Remodeled!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Wailea Condo Wailea Ekolu # 401, vacation rental in Wailea

Beautiful Wailea Condo Wailea Ekolu # 401

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wailea Ekolu #105 2Bd/2Ba Scenic Ocean View Great Location, Full A/C Sleeps 4, vacation rental in Wailea

Wailea Ekolu #105 2Bd/2Ba Scenic Ocean View Great Location, Full A/C Sleeps 4

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Prime Wailea 2 BDRM Condo Wailea Elua Village # 801, vacation rental in Wailea

Prime Wailea 2 BDRM Condo Wailea Elua Village # 801

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunningly Remodeled Ocean View Unit  -Wailea Ekahi #22D, vacation rental in Wailea

Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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MAKENA SURF RESORT, #C-102, vacation rental in Wailea

MAKENA SURF RESORT, #C-102

2 bedrooms
0 bathrooms
Sleeps 6
Match: Sleeps
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Wailea Ekahi Village 29F Ocean Front, vacation rental in Wailea

Wailea Ekahi Village 29F Ocean Front

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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WAILEA ELUA, #0702, vacation rental in Wailea

WAILEA ELUA, #0702

2 bedrooms
0 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful 1 Bdrm Ocean Front Condo-Wailea Elua #1602, vacation rental in Wailea

Beautiful 1 Bdrm Ocean Front Condo-Wailea Elua #1602

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Best Kihei Location; Oceanfront with Stunning Views; Spacious 2BR on the Beach!, vacation rental in Wailea

Best Kihei Location; Oceanfront with Stunning Views; Spacious 2BR on the Beach!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Prime Oceanfront 3Bd/3Ba Condo Wailea Elua #1305, vacation rental in Wailea

Prime Oceanfront 3Bd/3Ba Condo Wailea Elua #1305

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Blue Horizons K308 Wailea Beach Villas, vacation rental in Wailea

Blue Horizons K308 Wailea Beach Villas

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Aloha Kai Suite at Wailea Beach Villas PH 205, vacation rental in Wailea

Aloha Kai Suite at Wailea Beach Villas PH 205

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Ground Floor 2 BDRM Condo Wailea Elua Village # 105, vacation rental in Wailea

Lovely Ground Floor 2 BDRM Condo Wailea Elua Village # 105

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WOW !  WHAT A GREAT VIEW ! ---Great Reviews !, vacation rental in Wailea

WOW ! WHAT A GREAT VIEW ! ---Great Reviews !

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA, vacation rental in Wailea

OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Wailea Ekahi 7G Luxury Ocean Front S Maui Condo, vacation rental in Wailea

Wailea Ekahi 7G Luxury Ocean Front S Maui Condo

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Wailea Ekahi 11f:  Ocean View/Remodel 2 BR Condo, vacation rental in Wailea

Wailea Ekahi 11f: Ocean View/Remodel 2 BR Condo

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW REMODEL 2020-65”SONY 4K UHD LED LCD TV & BOSE SURROUND SOUND- GORGEOUS GEM, vacation rental in Wailea

NEW REMODEL 2020-65”SONY 4K UHD LED LCD TV & BOSE SURROUND SOUND- GORGEOUS GEM

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Amazing Wailea Surf Villa at Wailea Beach Villas, vacation rental in Wailea

Amazing Wailea Surf Villa at Wailea Beach Villas

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!, vacation rental in Wailea

The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious Tropical Retreat  Wailea Ekahi Unit - 31 D, vacation rental in Wailea

Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Luxurious 2.5 Bedroom - Flexible Rebooking if Needed!, vacation rental in Wailea

Luxurious 2.5 Bedroom - Flexible Rebooking if Needed!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ekahi 40A - Walk to the Beach from a Quiet Private Garden Oasis, vacation rental in Wailea

Ekahi 40A - Walk to the Beach from a Quiet Private Garden Oasis

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy the Amazing View and have a Mai Tai too!, vacation rental in Wailea

Enjoy the Amazing View and have a Mai Tai too!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Wow - Incredible Ocean Views - Beautifully Remodeled, vacation rental in Wailea

Wow - Incredible Ocean Views - Beautifully Remodeled

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Stunning Ocean/Sunset View in Gorgeous, Updated Wailea Grand Champions 166, vacation rental in Wailea

Stunning Ocean/Sunset View in Gorgeous, Updated Wailea Grand Champions 166

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wailea, Oceanfront, Luxury, Polo Beach Club Condo #403, vacation rental in Wailea

Wailea, Oceanfront, Luxury, Polo Beach Club Condo #403

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Azure Azul M212 at Wailea Beach Villas, vacation rental in Wailea

Azure Azul M212 at Wailea Beach Villas

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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On the beach, totally renovated, 5 star everything, vacation rental in Wailea

On the beach, totally renovated, 5 star everything

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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5D - One of the closest to the Beach, Recently remodeled and very well equipped., vacation rental in Wailea

5D - One of the closest to the Beach, Recently remodeled and very well equipped.

1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Largest Two Bedroom/ Two Bath in the Village! Sleeps Eight. Close to the Beach., vacation rental in Wailea

Largest Two Bedroom/ Two Bath in the Village! Sleeps Eight. Close to the Beach.

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing view, Closest to the beach, Wailea Ekahi, Unit 20i., vacation rental in Wailea

Amazing view, Closest to the beach, Wailea Ekahi, Unit 20i.

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury, Fully Remodeled! Ocean & Golf Views! NEW Split AC & Local Gym Pass Incl, vacation rental in Wailea

Luxury, Fully Remodeled! Ocean & Golf Views! NEW Split AC & Local Gym Pass Incl

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury at its Best W/ Big Ocean Views!!, vacation rental in Wailea

Luxury at its Best W/ Big Ocean Views!!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Perfect Location for a Relaxing Getaway, vacation rental in Wailea

The Perfect Location for a Relaxing Getaway

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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1 BR Treetop Luxury from $150/nt, vacation rental in Wailea

1 BR Treetop Luxury from $150/nt

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gorgeous Luxury Ocean View Top Floor Corner Unit w/A/C, Pool, Free Parking/Wifi, vacation rental in Wailea

Gorgeous Luxury Ocean View Top Floor Corner Unit w/A/C, Pool, Free Parking/Wifi

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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New Contemporary Elegant: 4 Bd, 3Ba, 3811S.F. & Office: Wailea Beach Villas 208., vacation rental in Wailea

New Contemporary Elegant: 4 Bd, 3Ba, 3811S.F. & Office: Wailea Beach Villas 208.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Ground Floor 2 Bedroom Wailea Elua #307, vacation rental in Wailea

Stunning Ground Floor 2 Bedroom Wailea Elua #307

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Hawaiian Escape -Blue Golf Course, vacation rental in Wailea

Hawaiian Escape -Blue Golf Course

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!, vacation rental in Wailea

14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Frequently Asked Questions about Wailea

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.