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Holiday Rentals in Wailea

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266 rentals in Wailea.
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Grand Champions #51 is a 2Bd 2Ba is a large condo that sleeps 6. Great Rates!, holiday rental in Wailea

Grand Champions #51 is a 2Bd 2Ba is a large condo that sleeps 6. Great Rates!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wailea Ekolu #1207 2Bd/2Ba Ground Floor, Ocean View, Full A/C, Sleeps 6, holiday rental in Wailea

Wailea Ekolu #1207 2Bd/2Ba Ground Floor, Ocean View, Full A/C, Sleeps 6

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunny Surf E301 at Makena Surf, holiday rental in Wailea

Sunny Surf E301 at Makena Surf

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Upgraded Hoo'lei Vacation Rental- Spacious Interior- Easy Beach Access- Hoo'lei, holiday rental in Wailea

Upgraded Hoo'lei Vacation Rental- Spacious Interior- Easy Beach Access- Hoo'lei

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

Aloha Kai Suite at Wailea Beach Villas PH 205

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Remodeled Ocean Front Condo - Makena Surf Resort G-206, holiday rental in Wailea

Gorgeous Remodeled Ocean Front Condo - Makena Surf Resort G-206

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning, Remodeled, 2 Bedroom WAILEA EKOLU, #914, holiday rental in Wailea

Stunning, Remodeled, 2 Bedroom WAILEA EKOLU, #914

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA, holiday rental in Wailea

OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Wailea Ekahi 11f:  Ocean View/Remodel 2 BR Condo, holiday rental in Wailea

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Elua Village # 701 - Luxury 2b/2b with Ocean View, and Newly Remodeled!, holiday 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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Wailea Ekahi Ocean View 50A, holiday rental in Wailea

Wailea Ekahi Ocean View 50A

1 bedroom
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, holiday 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, holiday rental in Wailea

Amazing Wailea Surf Villa at Wailea Beach Villas

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WAILEA ELUA, #0702, holiday rental in Wailea

WAILEA ELUA, #0702

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

Luxurious 2.5 Bedroom - Flexible Rebooking if Needed!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Panoramic Ocean View In The Heart Of Wailea On Golf Course, holiday rental in Wailea

Panoramic Ocean View In The Heart Of Wailea On Golf Course

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy the Amazing View and have a Mai Tai too!, holiday 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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Ekahi 40A - Walk to the Beach from a Quiet Private Garden Oasis, holiday 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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Wailea Luxurious Beachfront  2br,2ba on Polo Beach Unit #408, holiday 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, Oceanfront, Luxury, Polo Beach Club Condo #403, holiday rental in Wailea

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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�GEORGEOUS Wailea Retreat!�Top tier UPGRADES. Very Spacious and Peaceful!�, holiday rental in Wailea

�GEORGEOUS Wailea Retreat!�Top tier UPGRADES. Very Spacious and Peaceful!�

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach-3 min walk, Remodeled, holiday 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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Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4, holiday 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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Stunning Ocean/Sunset View in Gorgeous, Updated Wailea Grand Champions 166, holiday 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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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!

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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New Contemporary Elegant: 4 Bd, 3Ba, 3811S.F. & Office: Wailea Beach Villas 208., holiday 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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The Perfect Location for a Relaxing Getaway, holiday rental in Wailea

The Perfect Location for a Relaxing Getaway

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!, holiday 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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Luxury, Fully Remodeled! Ocean & Golf Views! NEW Split AC & Local Gym Pass Incl, holiday 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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Amazing view, Closest to the beach, Wailea Ekahi, Unit 20i., holiday 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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GET-A-WAY WINTER AVAILABLE Luxury Wailea Dream Location, Full AC, BBQ and more, holiday rental in Wailea

GET-A-WAY WINTER AVAILABLE Luxury Wailea Dream Location, Full AC, BBQ and more

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

Luxury at its Best W/ Big Ocean Views!!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern Spacious Beachfront Luxury rental in Ekahi Village - Apartment 39F, holiday rental in Wailea

Modern Spacious Beachfront Luxury rental in Ekahi Village - Apartment 39F

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Grand Champions #48: Stunning 180 Degree Ocean Views. Top Floor Paradise Home, holiday 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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Largest Two Bedroom/ Two Bath in the Village! Sleeps Eight. Close to the Beach., holiday 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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April 5 to April 16 is still available!-Wailea Ekolu Oceanview 2B/, holiday rental in Wailea

April 5 to April 16 is still available!-Wailea Ekolu Oceanview 2B/

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ocean View,  Steps away from the pool, holiday rental in Wailea

Ocean View, Steps away from the pool

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

1 BR Treetop Luxury from $150/nt

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beachfront Section Immaculate Wailea Ekahi 1 Bd/2Ba Paradise Condominium 8E, holiday rental in Wailea

Beachfront Section Immaculate Wailea Ekahi 1 Bd/2Ba Paradise Condominium 8E

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Million Dollar Ocean & Golf Course Views from this beautiful 2 bed 2 bath Condo, holiday rental in Wailea

Million Dollar Ocean & Golf Course Views from this beautiful 2 bed 2 bath Condo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hear the waves from the lanai!  Very quiet and private unit!  Flat walk!  19C, holiday rental in Wailea

Hear the waves from the lanai! Very quiet and private unit! Flat walk! 19C

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Availability in this Quiet, Spacious 1 Bdrm/2 Bath!, holiday rental in Wailea

Availability in this Quiet, Spacious 1 Bdrm/2 Bath!

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Gorgeous Luxury Ocean View Top Floor Corner Unit w/A/C, Pool, Free Parking/Wifi, holiday 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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Treetop Studio from $120/night, holiday rental in Wailea

Treetop Studio from $120/night

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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COMPLETE REMODEL!  EVERY ITEM BRAND NEW!!! AC and POOL!, holiday rental in Wailea

COMPLETE REMODEL! EVERY ITEM BRAND NEW!!! AC and POOL!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Remodeled Spacious Ground Floor Unit -Wailea Ekahi #22B, holiday rental in Wailea

Newly Remodeled Spacious Ground Floor Unit -Wailea Ekahi #22B

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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FULL OCEAN VIEW WAILEA, holiday rental in Wailea

FULL OCEAN VIEW WAILEA

2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Oceanview Beautifully Renovated Kihei Condo D206, holiday rental in Wailea

Oceanview Beautifully Renovated Kihei Condo D206

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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