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Holiday Rentals in Wailea

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330 rentals in Wailea.
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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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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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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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Royal Mauian 411: Direct Oceanfront, Total Privacy, Best Location!! With A/C!, holiday 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 #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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Palms at Wailea #1902 Garden View 2Bd/2Ba, Fully Air Conditioned, Sleeps 6, holiday rental in Wailea

Palms at Wailea #1902 Garden View 2Bd/2Ba, Fully Air Conditioned, Sleeps 6

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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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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Beautiful Wailea Condo Wailea Ekolu # 401, holiday 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, holiday 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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MAKENA SURF RESORT, #C-102, holiday rental in Wailea

MAKENA SURF RESORT, #C-102

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

Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D

1 bedroom
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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Prime Wailea 2 BDRM Condo Wailea Elua Village # 801, holiday rental in Wailea

Prime Wailea 2 BDRM Condo Wailea Elua Village # 801

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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Wailea Ekahi Village 29F Ocean Front, holiday rental in Wailea

Wailea Ekahi Village 29F Ocean Front

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury 2 Bedroom 2nd Floor Condo Wailea Elua #2204, holiday rental in Wailea

Luxury 2 Bedroom 2nd Floor Condo Wailea Elua #2204

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful 1 Bdrm Ocean Front Condo-Wailea Elua #1602, holiday rental in Wailea

Beautiful 1 Bdrm Ocean Front Condo-Wailea Elua #1602

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Spectacular Ground Floor Unit - Wailea Grand Champions #173, holiday rental in Wailea

Spectacular Ground Floor Unit - Wailea Grand Champions #173

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

Blue Horizons K308 Wailea Beach Villas

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Best Kihei Location; Oceanfront with Stunning Views; Spacious 2BR on the Beach!, holiday 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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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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WOW !  WHAT A GREAT VIEW ! ---Great Reviews !, holiday 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, 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 7G Luxury Ocean Front S Maui Condo, holiday 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, 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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Wailea Sunset Estate, holiday rental in Wailea

Wailea Sunset Estate

5 bedrooms
6 bathrooms
Sleeps 10
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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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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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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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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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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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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Wow - Incredible Ocean Views - Beautifully Remodeled, holiday 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, 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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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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On the beach, totally renovated, 5 star everything, holiday rental in Wailea

On the beach, totally renovated, 5 star everything

2 bedrooms
2 bathrooms
Sleeps 5
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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5D - One of the closest to the Beach, Recently remodeled and very well equipped., holiday 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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Azure Azul M212 at Wailea Beach Villas, holiday rental in Wailea

Azure Azul M212 at Wailea Beach Villas

3 bedrooms
3 bathrooms
Sleeps 6
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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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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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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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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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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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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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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