Family Friendly Villas For Families - Vacation Rentals in Po'olenalena Beach

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From US $1,012

         

10.0 (199 Reviews)

Cottage

Hawaiian Cottage and Personal Paradise/BBKM 2013/0004

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $420

         

10.0 (1 Review)

House

Hale Hui Kai #112

• Pool
• View
• Wheelchair Accessible

• Hawaii
• Kihei

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From US $1,151

         

|

10.0 (7 Reviews)

Condo

Luxurious Wailea Ocean Vistas

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $548

         

10.0 (151 Reviews)

Cottage

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $518

         

New

House

Keawakapu by Coldwell Banker Island Vacations

• Parking
• Wheelchair Accessible
• Child Friendly

• Hawaii
• Kihei

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From US $2,289

         

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10.0 (2 Reviews)

Condo

Grand Champions Condos by KBM

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $672

         

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 US $2,512

         

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10.0 (4 Reviews)

Resort

Ho'olei at Grand Wailea

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $1,895

         

|

10.0 (2 Reviews)

Condo

Polo Beach Club Vacation Rentals - APlus Resorts

• Air Conditioner
• Pool
• TV

• Kihei
• Wailea

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From US $942

         

10.0 (130 Reviews)

Condo

5-StarMAUI Paradise:Newly Remodeled Ocean-End Beachfront Condo 30%off12/19-12/26

• Air Conditioner
• Parking
• Pool

• Hawaii
• Kihei

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From US $1,564

         

10.0 (113 Reviews)

Condo

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

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $1,563

         

10.0 (97 Reviews)

Condo

Beachfront Condo B303

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $560

         

10.0 (54 Reviews)

Condo

Maui Family Owned & Managed - Wailea Grand Champions Villa

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $840

         

9.8 (188 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 US $600

         

9.8 (156 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 US $480

         

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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From US $428

         

9.8 (102 Reviews)

Condo

Wailea Ekahi 51F Oceanview - Walk to Beach

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $788

         

9.8 (36 Reviews)

Condo

Beachfront Condo E 303/Incredible views/Spring Break 2026 Available/Pickleball

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $868

         

10.0 (80 Reviews)

Condo

Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $1,100

         

10.0 (64 Reviews)

Condo

Wailea Elua Resort Gorgeous Remodel #1507

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $617

         

9.6 (43 Reviews)

Condo

Beautifully Remodeled with Central A/C! Top Floor! Palms at Wailea 206

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $727

         

10.0 (53 Reviews)

Condo

Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $1,656

         

10.0 (42 Reviews)

Villa

I.P.M PRESENTS: HOOLEI 69-2: GREAT LOCATION + STUNNING NEW REMODEL! WOW!

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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From US $534

         

9.8 (113 Reviews)

Condo

Just another day in Paradise!

• Air Conditioner
• Parking
• Pool

• Kihei
• Wailea

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