Castleinhawaii - Vacation Rentals in Maui's Winery

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From $420

         

10.0 (1 Review)

House

Hale Hui Kai #112

• Pool
• View
• Wheelchair Accessible

• Hawaii
• Kihei

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From $1,006

         

10.0 (196 Reviews)

Cottage

Hawaiian Cottage and Personal Paradise/BBKM 2013/0004

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $778

         

|

10.0 (122 Reviews)

Condo

130 m² Condo ∙ 3 bedrooms ∙ 8 guests

• 1395 ft² Condo
• Air Conditioner
• Parking
• Pool

• Hawaii
• Kihei

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From $336

         

|

10.0 (8 Reviews)

Bed & Breakfast

Papaya Suite

• Air Conditioner
• Parking
• TV

• Hawaii
• Kihei

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From $518

         

New

House

Keawakapu by Coldwell Banker Island Vacations

• Parking
• Wheelchair Accessible
• Child Friendly

• Hawaii
• Kihei

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From $557

         

10.0 (148 Reviews)

Cottage

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $1,016

         

|

10.0 (119 Reviews)

Villa

225 m² Villa ∙ 3 bedrooms ∙ 10 guests

• 2426 ft² Villa
• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $1,151

         

|

10.0 (7 Reviews)

Condo

Luxurious Wailea Ocean Vistas

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $2,512

         

|

10.0 (5 Reviews)

Resort

Ho'olei at Grand Wailea

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $654

         

10.0 (131 Reviews)

Condo

Amazing view, Close to the beach, Wailea Ekahi Unit 20i

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $750

         

|

10.0 (115 Reviews)

Condo

130 m² Condo ∙ 3 bedrooms ∙ 8 guests

• 1395 ft² Condo
• Air Conditioner
• Parking
• Pool

• Hawaii
• Kihei

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From $298

         

|

10.0 (4 Reviews)

Bed & Breakfast

Maui What A Wonderful B&B Pineapple Ste

• Air Conditioner
• Parking
• TV

• Hawaii
• Kihei

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From $511

         

|

10.0 (4 Reviews)

Apartment

Wailea Ekahi 21F

• Pool
• Security/Safety
• Guest Services

• Kihei
• Wailea

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From $964

         

10.0 (128 Reviews)

Condo

New Luxury Remodel, Ocean End, On the Beach! 5-STAR Luxury Condo In Resort

• Air Conditioner
• Parking
• Pool

• Hawaii
• Kihei

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From $184

         

10.0 (4 Reviews)

House

Keawakapu 206

• Parking
• View
• Security/Safety

• Hawaii
• Kihei

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From $1,106

         

10.0 (109 Reviews)

Condo

F207 Spectacular Ocean Views - Beautifully Renovated Condo - 2 New Pools

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $1,490

         

|

10.0 (2 Reviews)

Apartment

Grand Champions by KBM Resorts

• Air Conditioner
• Parking
• Pet Friendly

• Kihei
• Wailea

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From $786

         

10.0 (93 Reviews)

Condo

Beachfront Condo B303 - Oct 9-22 still available

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $803

         

|

10.0 (2 Reviews)

House

Elua 406

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $591

         

10.0 (53 Reviews)

Condo

Maui Family Owned & Managed - Wailea Grand Champions Villa

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $689

         

|

10.0 (2 Reviews)

Apartment

Luxurious & Spacious Ocean Vistas

• Air Conditioner
• Parking
• Pool

• Hawaii
• Kihei

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From $875

         

9.8 (187 Reviews)

Condo

Largest Two Bedroom/Two Bath in the Village, Sleeps Eight & Close to the Beach

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $519

         

9.8 (155 Reviews)

Condo

Soooooo Close to the Beach & Completely Remodeled! Relax to the Sound of Waves

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From $490

         

9.8 (102 Reviews)

Condo

Vacation in Paradise at our charming condo by the best of everything Maui offers

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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★ Pro Tip: Castleinhawaii makes it easy to compare the best listings on Castleinhawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Castleinhawaii homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Maui's Winery.