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Wailea Villas

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5 mi
356 rentals in Wailea.
Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!, vacation rental in Wailea
Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!, vacation rental in Wailea
Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!, vacation rental in Wailea

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
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Wailea Ekolu #105 Partial Ocean view, Sleeps 4, vacation rental in Wailea
Wailea Ekolu #105 Partial Ocean view, Sleeps 4, vacation rental in Wailea
Wailea Ekolu #105 Partial Ocean view, Sleeps 4, vacation rental in Wailea

Wailea Ekolu #105 Partial Ocean view, Sleeps 4

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Ocean View Wailea Beach Villa- Book & Save, vacation rental in Wailea
Stunning Ocean View Wailea Beach Villa- Book & Save, vacation rental in Wailea
Stunning Ocean View Wailea Beach Villa- Book & Save, vacation rental in Wailea

Stunning Ocean View Wailea Beach Villa- Book & Save

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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�Georgeous 5-STAR Wailea Retreat!Tranquil Corner unit, Top tier Upgrades�, vacation rental in Wailea
�Georgeous 5-STAR Wailea Retreat!Tranquil Corner unit, Top tier Upgrades�, vacation rental in Wailea
�Georgeous 5-STAR Wailea Retreat!Tranquil Corner unit, Top tier Upgrades�, vacation rental in Wailea

�Georgeous 5-STAR Wailea Retreat!Tranquil Corner unit, Top tier Upgrades�

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning views with walking distance to the beach! Wailea Ekahi 49F., vacation rental in Wailea
Stunning views with walking distance to the beach! Wailea Ekahi 49F., vacation rental in Wailea
Stunning views with walking distance to the beach! Wailea Ekahi 49F., vacation rental in Wailea

Stunning views with walking distance to the beach! Wailea Ekahi 49F.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Palms at Wailea 303 will be your new favorite! Clean & beautifully remodeled, vacation rental in Wailea
Palms at Wailea 303 will be your new favorite! Clean & beautifully remodeled, vacation rental in Wailea
Palms at Wailea 303 will be your new favorite! Clean & beautifully remodeled, vacation rental in Wailea

Palms at Wailea 303 will be your new favorite! Clean & beautifully remodeled

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean View,  Steps away from the pool, vacation rental in Wailea
Ocean View,  Steps away from the pool, vacation rental in Wailea
Ocean View,  Steps away from the pool, vacation rental in Wailea

Ocean View, Steps away from the pool

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach, vacation rental in Wailea
Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach, vacation rental in Wailea
Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach, vacation rental in Wailea

Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Direct Ocean Front Polo Beach 805!, vacation rental in Wailea
Direct Ocean Front Polo Beach 805!, vacation rental in Wailea
Direct Ocean Front Polo Beach 805!, vacation rental in Wailea

Direct Ocean Front Polo Beach 805!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New! Luxurious 3bd Villa at Wailea Beach Villas, vacation rental in Wailea
New! Luxurious 3bd Villa at Wailea Beach Villas, vacation rental in Wailea
New! Luxurious 3bd Villa at Wailea Beach Villas, vacation rental in Wailea

New! Luxurious 3bd Villa at Wailea Beach Villas

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms, vacation rental in Wailea
Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms, vacation rental in Wailea
Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms, vacation rental in Wailea

Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!, vacation rental in Wailea
WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!, vacation rental in Wailea
WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!, vacation rental in Wailea

WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai, vacation rental in Wailea
Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai, vacation rental in Wailea
Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai, vacation rental in Wailea

Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai

Condo/Apartment
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!, vacation rental in Wailea
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!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Kihei Surfside #609: Oceanfront Gem with Stunning Views and Comfort, vacation rental in Wailea
Kihei Surfside #609: Oceanfront Gem with Stunning Views and Comfort, vacation rental in Wailea
Kihei Surfside #609: Oceanfront Gem with Stunning Views and Comfort, vacation rental in Wailea

Kihei Surfside #609: Oceanfront Gem with Stunning Views and Comfort

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING, vacation rental in Wailea
COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING, vacation rental in Wailea
COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING, vacation rental in Wailea

COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4, vacation rental in Wailea
Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4, vacation rental in Wailea
Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4, vacation rental in Wailea

Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!, vacation rental in Wailea
Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!, vacation rental in Wailea
Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!, vacation rental in Wailea

Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Direct ocean front, Polo Beach Club 705!, vacation rental in Wailea
Direct ocean front, Polo Beach Club 705!, vacation rental in Wailea
Direct ocean front, Polo Beach Club 705!, vacation rental in Wailea

Direct ocean front, Polo Beach Club 705!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palms at Wailea 603 2bd 2ba Sleeps 6  Great Rates!!, vacation rental in Wailea
Palms at Wailea 603 2bd 2ba Sleeps 6  Great Rates!!, vacation rental in Wailea
Palms at Wailea 603 2bd 2ba Sleeps 6  Great Rates!!, vacation rental in Wailea

Palms at Wailea 603 2bd 2ba Sleeps 6 Great Rates!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Wailea Ekahi Condominium, vacation rental in Wailea
Charming Wailea Ekahi Condominium, vacation rental in Wailea
Charming Wailea Ekahi Condominium, vacation rental in Wailea

Charming Wailea Ekahi Condominium

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Palms at Wailea #307 Elegantly Remodeled, Ground Floor Unit, Ocean View, Wifi, vacation rental in Wailea
Palms at Wailea #307 Elegantly Remodeled, Ground Floor Unit, Ocean View, Wifi, vacation rental in Wailea
Palms at Wailea #307 Elegantly Remodeled, Ground Floor Unit, Ocean View, Wifi, vacation rental in Wailea

Palms at Wailea #307 Elegantly Remodeled, Ground Floor Unit, Ocean View, Wifi

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A/C, vacation rental in Wailea
Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A/C, vacation rental in Wailea
Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A/C, vacation rental in Wailea

Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A/C

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Amazing location!   Hear the waves from the quiet and private lanai!  19C, vacation rental in Wailea
Amazing location!   Hear the waves from the quiet and private lanai!  19C, vacation rental in Wailea
Amazing location!   Hear the waves from the quiet and private lanai!  19C, vacation rental in Wailea

Amazing location! Hear the waves from the quiet and private lanai! 19C

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Wailea Ekahi Village | 38F, vacation rental in Wailea
Wailea Ekahi Village | 38F, vacation rental in Wailea
Wailea Ekahi Village | 38F, vacation rental in Wailea

Wailea Ekahi Village | 38F

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wailea Ekahi 52B | Resort Level Amenities!, vacation rental in Wailea
Wailea Ekahi 52B | Resort Level Amenities!, vacation rental in Wailea
Wailea Ekahi 52B | Resort Level Amenities!, vacation rental in Wailea

Wailea Ekahi 52B | Resort Level Amenities!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Wailea Ekahi Studio #48-D Gorgeous Studio,  Keawakapu Beach, vacation rental in Wailea
Wailea Ekahi Studio #48-D Gorgeous Studio,  Keawakapu Beach, vacation rental in Wailea
Wailea Ekahi Studio #48-D Gorgeous Studio,  Keawakapu Beach, vacation rental in Wailea

Wailea Ekahi Studio #48-D Gorgeous Studio, Keawakapu Beach

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Ekahi 48B Garden View Studio, vacation rental in Wailea
Ekahi 48B Garden View Studio, vacation rental in Wailea
Ekahi 48B Garden View Studio, vacation rental in Wailea

Ekahi 48B Garden View Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wailea Elua Village | 2004, vacation rental in Wailea
Wailea Elua Village | 2004, vacation rental in Wailea
Wailea Elua Village | 2004, vacation rental in Wailea

Wailea Elua Village | 2004

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Wailea Ekahi Village | 12E, vacation rental in Wailea
Wailea Ekahi Village | 12E, vacation rental in Wailea
Wailea Ekahi Village | 12E, vacation rental in Wailea

Wailea Ekahi Village | 12E

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Wailea Elua Village | 2012, vacation rental in Wailea
Wailea Elua Village | 2012, vacation rental in Wailea
Wailea Elua Village | 2012, vacation rental in Wailea

Wailea Elua Village | 2012

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Wailea Elua Village | 1102, vacation rental in Wailea
Wailea Elua Village | 1102, vacation rental in Wailea
Wailea Elua Village | 1102, vacation rental in Wailea

Wailea Elua Village | 1102

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Wailea Elua Village | 1301, vacation rental in Wailea
Wailea Elua Village | 1301, vacation rental in Wailea
Wailea Elua Village | 1301, vacation rental in Wailea

Wailea Elua Village | 1301

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Updated Wailea Condo in Oceanfront Complex!, vacation rental in Wailea
Updated Wailea Condo in Oceanfront Complex!, vacation rental in Wailea
Updated Wailea Condo in Oceanfront Complex!, vacation rental in Wailea

Updated Wailea Condo in Oceanfront Complex!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Romantic 1 BR Condo with King Tempurpedic, vacation rental in Wailea
Romantic 1 BR Condo with King Tempurpedic, vacation rental in Wailea
Romantic 1 BR Condo with King Tempurpedic, vacation rental in Wailea

Romantic 1 BR Condo with King Tempurpedic

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beaut Secluded Resort in Renowned  Gently Sloping Hills & Verdant Norfolk Pines, vacation rental in Wailea
Beaut Secluded Resort in Renowned  Gently Sloping Hills & Verdant Norfolk Pines, vacation rental in Wailea
Beaut Secluded Resort in Renowned  Gently Sloping Hills & Verdant Norfolk Pines, vacation rental in Wailea

Beaut Secluded Resort in Renowned Gently Sloping Hills & Verdant Norfolk Pines

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular Oceanfront Views - Cool off W/ AC – Ground Level Kihei Surfside 109, vacation rental in Wailea
Spectacular Oceanfront Views - Cool off W/ AC – Ground Level Kihei Surfside 109, vacation rental in Wailea
Spectacular Oceanfront Views - Cool off W/ AC – Ground Level Kihei Surfside 109, vacation rental in Wailea

Spectacular Oceanfront Views - Cool off W/ AC – Ground Level Kihei Surfside 109

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Maui Retreat Ekahi 50F,  All YOU Need!, vacation rental in Wailea
Maui Retreat Ekahi 50F,  All YOU Need!, vacation rental in Wailea
Maui Retreat Ekahi 50F,  All YOU Need!, vacation rental in Wailea

Maui Retreat Ekahi 50F, All YOU Need!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Aloha Moon - The Honeymoon Hideaway, vacation rental in Wailea
Aloha Moon - The Honeymoon Hideaway, vacation rental in Wailea
Aloha Moon - The Honeymoon Hideaway, vacation rental in Wailea

Aloha Moon - The Honeymoon Hideaway

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Experience the Magic of Maui at Ekahi 13C, vacation rental in Wailea
Experience the Magic of Maui at Ekahi 13C, vacation rental in Wailea
Experience the Magic of Maui at Ekahi 13C, vacation rental in Wailea

Experience the Magic of Maui at Ekahi 13C

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Wailea Ekahi Village | 54B, vacation rental in Wailea
Wailea Ekahi Village | 54B, vacation rental in Wailea
Wailea Ekahi Village | 54B, vacation rental in Wailea

Wailea Ekahi Village | 54B

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Ekahi 49D, Big Ocean Views, 2nd floor, vacation rental in Wailea
Ekahi 49D, Big Ocean Views, 2nd floor, vacation rental in Wailea
Ekahi 49D, Big Ocean Views, 2nd floor, vacation rental in Wailea

Ekahi 49D, Big Ocean Views, 2nd floor

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Tranquil Oceanview Corner Unit with Dual Lanais - Ekahi 22D - Soak Up the Sun!, vacation rental in Wailea
Tranquil Oceanview Corner Unit with Dual Lanais - Ekahi 22D - Soak Up the Sun!, vacation rental in Wailea
Tranquil Oceanview Corner Unit with Dual Lanais - Ekahi 22D - Soak Up the Sun!, vacation rental in Wailea

Tranquil Oceanview Corner Unit with Dual Lanais - Ekahi 22D - Soak Up the Sun!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Rare Ocean Front 1 Bdrm w/ AC! - Starting * $234.00/night - Royal Mauian #209, vacation rental in Wailea
Rare Ocean Front 1 Bdrm w/ AC! - Starting * $234.00/night - Royal Mauian #209, vacation rental in Wailea
Rare Ocean Front 1 Bdrm w/ AC! - Starting * $234.00/night - Royal Mauian #209, vacation rental in Wailea

Rare Ocean Front 1 Bdrm w/ AC! - Starting * $234.00/night - Royal Mauian #209

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ekahi 49E Sweeping Ocean Views, vacation rental in Wailea
Ekahi 49E Sweeping Ocean Views, vacation rental in Wailea
Ekahi 49E Sweeping Ocean Views, vacation rental in Wailea

Ekahi 49E Sweeping Ocean Views

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Polo Beach Club  |  102, vacation rental in Wailea
Polo Beach Club  |  102, vacation rental in Wailea
Polo Beach Club  |  102, vacation rental in Wailea

Polo Beach Club | 102

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Ocean Views, AC in every room, remodeled,  #504, vacation rental in Wailea
Amazing Ocean Views, AC in every room, remodeled,  #504, vacation rental in Wailea
Amazing Ocean Views, AC in every room, remodeled,  #504, vacation rental in Wailea

Amazing Ocean Views, AC in every room, remodeled, #504

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!, vacation rental in Wailea
Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!, vacation rental in Wailea
Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!, vacation rental in Wailea

Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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, vacation rental in Wailea
Luxurious Tropical Retreat  Wailea Ekahi Unit - 31 D, vacation rental in Wailea

Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Gorgeously Updated - Kihei Surfside #113 - Groundlevel Oceanfront Condo, vacation rental in Wailea
Gorgeously Updated - Kihei Surfside #113 - Groundlevel Oceanfront Condo, vacation rental in Wailea
Gorgeously Updated - Kihei Surfside #113 - Groundlevel Oceanfront Condo, vacation rental in Wailea

Gorgeously Updated - Kihei Surfside #113 - Groundlevel Oceanfront Condo

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 356
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.
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.
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