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Holiday Rentals in Wailea

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5 km
357 rentals in Wailea.
Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!, holiday rental in Wailea
Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!, holiday rental in Wailea
Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!, holiday 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, holiday rental in Wailea
Wailea Ekolu #105 Partial Ocean view, Sleeps 4, holiday rental in Wailea
Wailea Ekolu #105 Partial Ocean view, Sleeps 4, holiday 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, holiday rental in Wailea
Stunning Ocean View Wailea Beach Villa- Book & Save, holiday rental in Wailea
Stunning Ocean View Wailea Beach Villa- Book & Save, holiday rental in Wailea

Stunning Ocean View Wailea Beach Villa- Book & Save

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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�Georgeous 5-STAR Wailea Retreat!Tranquil Corner unit, Top tier Upgrades�, holiday rental in Wailea
�Georgeous 5-STAR Wailea Retreat!Tranquil Corner unit, Top tier Upgrades�, holiday rental in Wailea
�Georgeous 5-STAR Wailea Retreat!Tranquil Corner unit, Top tier Upgrades�, holiday 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., holiday rental in Wailea
Stunning views with walking distance to the beach! Wailea Ekahi 49F., holiday rental in Wailea
Stunning views with walking distance to the beach! Wailea Ekahi 49F., holiday 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, holiday rental in Wailea
Palms at Wailea 303 will be your new favorite! Clean & beautifully remodeled, holiday rental in Wailea
Palms at Wailea 303 will be your new favorite! Clean & beautifully remodeled, holiday 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, holiday rental in Wailea
Ocean View,  Steps away from the pool, holiday rental in Wailea
Ocean View,  Steps away from the pool, holiday 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, holiday rental in Wailea
Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach, holiday rental in Wailea
Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach, holiday 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!, holiday rental in Wailea
Direct Ocean Front Polo Beach 805!, holiday rental in Wailea
Direct Ocean Front Polo Beach 805!, holiday 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, holiday rental in Wailea
New! Luxurious 3bd Villa at Wailea Beach Villas, holiday rental in Wailea
New! Luxurious 3bd Villa at Wailea Beach Villas, holiday 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, holiday rental in Wailea
Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms, holiday rental in Wailea
Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms, holiday 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!, holiday rental in Wailea
WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!, holiday rental in Wailea
WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!, holiday rental in Wailea

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

Holiday Rental House
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, holiday rental in Wailea
Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai, holiday rental in Wailea
Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai, holiday rental in Wailea

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!, holiday rental in Wailea
14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!, holiday rental in Wailea
14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!, holiday 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, holiday rental in Wailea
Kihei Surfside #609: Oceanfront Gem with Stunning Views and Comfort, holiday rental in Wailea
Kihei Surfside #609: Oceanfront Gem with Stunning Views and Comfort, holiday 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, holiday rental in Wailea
COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING, holiday rental in Wailea
COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING, holiday 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, holiday rental in Wailea
Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4, holiday rental in Wailea
Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4, holiday 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!, holiday rental in Wailea
Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!, holiday rental in Wailea
Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!, holiday 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!, holiday rental in Wailea
Direct ocean front, Polo Beach Club 705!, holiday rental in Wailea
Direct ocean front, Polo Beach Club 705!, holiday 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!!, holiday rental in Wailea
Palms at Wailea 603 2bd 2ba Sleeps 6  Great Rates!!, holiday rental in Wailea
Palms at Wailea 603 2bd 2ba Sleeps 6  Great Rates!!, holiday 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, holiday rental in Wailea
Charming Wailea Ekahi Condominium, holiday rental in Wailea
Charming Wailea Ekahi Condominium, holiday 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, holiday rental in Wailea
Palms at Wailea #307 Elegantly Remodeled, Ground Floor Unit, Ocean View, Wifi, holiday rental in Wailea
Palms at Wailea #307 Elegantly Remodeled, Ground Floor Unit, Ocean View, Wifi, holiday 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, holiday rental in Wailea
Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A/C, holiday rental in Wailea
Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A/C, holiday 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, holiday rental in Wailea
Amazing location!   Hear the waves from the quiet and private lanai!  19C, holiday rental in Wailea
Amazing location!   Hear the waves from the quiet and private lanai!  19C, holiday rental in Wailea

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Wailea Ekahi Village | 38F, holiday rental in Wailea
Wailea Ekahi Village | 38F, holiday rental in Wailea
Wailea Ekahi Village | 38F, holiday 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!, holiday rental in Wailea
Wailea Ekahi 52B | Resort Level Amenities!, holiday rental in Wailea
Wailea Ekahi 52B | Resort Level Amenities!, holiday 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, holiday rental in Wailea
Wailea Ekahi Studio #48-D Gorgeous Studio,  Keawakapu Beach, holiday rental in Wailea
Wailea Ekahi Studio #48-D Gorgeous Studio,  Keawakapu Beach, holiday rental in Wailea

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Ekahi 48B Garden View Studio, holiday rental in Wailea
Ekahi 48B Garden View Studio, holiday rental in Wailea
Ekahi 48B Garden View Studio, holiday 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, holiday rental in Wailea
Wailea Elua Village | 2004, holiday rental in Wailea
Wailea Elua Village | 2004, holiday 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, holiday rental in Wailea
Wailea Ekahi Village | 12E, holiday rental in Wailea
Wailea Ekahi Village | 12E, holiday 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, holiday rental in Wailea
Wailea Elua Village | 2012, holiday rental in Wailea
Wailea Elua Village | 2012, holiday rental in Wailea

Wailea Elua Village | 2012

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Wailea Elua Village | 1301, holiday rental in Wailea
Wailea Elua Village | 1301, holiday rental in Wailea
Wailea Elua Village | 1301, holiday rental in Wailea

Wailea Elua Village | 1301

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Wailea Elua Village | 1102, holiday rental in Wailea
Wailea Elua Village | 1102, holiday rental in Wailea
Wailea Elua Village | 1102, holiday rental in Wailea

Wailea Elua Village | 1102

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Updated Wailea Condo in Oceanfront Complex!, holiday rental in Wailea
Updated Wailea Condo in Oceanfront Complex!, holiday rental in Wailea
Updated Wailea Condo in Oceanfront Complex!, holiday 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, holiday rental in Wailea
Romantic 1 BR Condo with King Tempurpedic, holiday rental in Wailea
Romantic 1 BR Condo with King Tempurpedic, holiday 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, holiday rental in Wailea
Beaut Secluded Resort in Renowned  Gently Sloping Hills & Verdant Norfolk Pines, holiday rental in Wailea
Beaut Secluded Resort in Renowned  Gently Sloping Hills & Verdant Norfolk Pines, holiday rental in Wailea

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular Oceanfront Views - Cool off W/ AC – Ground Level Kihei Surfside 109, holiday rental in Wailea
Spectacular Oceanfront Views - Cool off W/ AC – Ground Level Kihei Surfside 109, holiday rental in Wailea
Spectacular Oceanfront Views - Cool off W/ AC – Ground Level Kihei Surfside 109, holiday 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!, holiday rental in Wailea
Maui Retreat Ekahi 50F,  All YOU Need!, holiday rental in Wailea
Maui Retreat Ekahi 50F,  All YOU Need!, holiday 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, holiday rental in Wailea
Aloha Moon - The Honeymoon Hideaway, holiday rental in Wailea
Aloha Moon - The Honeymoon Hideaway, holiday 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, holiday rental in Wailea
Experience the Magic of Maui at Ekahi 13C, holiday rental in Wailea
Experience the Magic of Maui at Ekahi 13C, holiday 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, holiday rental in Wailea
Wailea Ekahi Village | 54B, holiday rental in Wailea
Wailea Ekahi Village | 54B, holiday 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, holiday rental in Wailea
Ekahi 49D, Big Ocean Views, 2nd floor, holiday rental in Wailea
Ekahi 49D, Big Ocean Views, 2nd floor, holiday 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!, holiday rental in Wailea
Tranquil Oceanview Corner Unit with Dual Lanais - Ekahi 22D - Soak Up the Sun!, holiday rental in Wailea
Tranquil Oceanview Corner Unit with Dual Lanais - Ekahi 22D - Soak Up the Sun!, holiday 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, holiday rental in Wailea
Rare Ocean Front 1 Bdrm w/ AC! - Starting * $234.00/night - Royal Mauian #209, holiday rental in Wailea
Rare Ocean Front 1 Bdrm w/ AC! - Starting * $234.00/night - Royal Mauian #209, holiday 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, holiday rental in Wailea
Ekahi 49E Sweeping Ocean Views, holiday rental in Wailea
Ekahi 49E Sweeping Ocean Views, holiday rental in Wailea

Ekahi 49E Sweeping Ocean Views

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Polo Beach Club  |  102, holiday rental in Wailea
Polo Beach Club  |  102, holiday rental in Wailea
Polo Beach Club  |  102, holiday 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, holiday rental in Wailea
Amazing Ocean Views, AC in every room, remodeled,  #504, holiday rental in Wailea
Amazing Ocean Views, AC in every room, remodeled,  #504, holiday 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!, holiday rental in Wailea
Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!, holiday rental in Wailea
Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!, holiday 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, holiday rental in Wailea
Luxurious Tropical Retreat  Wailea Ekahi Unit - 31 D, holiday rental in Wailea
Luxurious Tropical Retreat  Wailea Ekahi Unit - 31 D, holiday rental in Wailea

Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D

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

Gorgeously Updated - Kihei Surfside #113 - Groundlevel Oceanfront Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 357
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