Vacation rentals in Wailea, HI

Best vacation rentals and Airbnb offers in Wailea, HI

10 ★ 4 reviews

Grand Champions by KBM

Condo, Wailea

Grand Champions by KBM is a condo in Wailea, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Grand Champions by KBM

Grand Champions by KBM is a condo in Wailea, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, with kitchen, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $6,321.

From$594/night

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10 ★ 2 reviews

Polo Beach Club Vacation Rentals - APlus Resorts

Condo, Wailea

Polo Beach Club Vacation Rentals - APlus Resorts is a condo in Wailea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Polo Beach Club Vacation Rentals - APlus Resorts

Polo Beach Club Vacation Rentals - APlus Resorts is a condo in Wailea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, with kitchen, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $6,867.

From$673/night

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9.6 ★ 254 reviews

Wailea Elua- CoralTree Residence Collection

Apartment, Wailea

Wailea Elua- CoralTree Residence Collection is a apartment in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Wailea Elua- CoralTree Residence Collection

Wailea Elua- CoralTree Residence Collection is a apartment in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,519.

From$575/night

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9 ★ 64 reviews

Polo Beach - CoralTree Residence Collection

Apartment, Wailea

Polo Beach - CoralTree Residence Collection is a apartment in Wailea, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Polo Beach - CoralTree Residence Collection

Polo Beach - CoralTree Residence Collection is a apartment in Wailea, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,234.

From$765/night

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Pet-friendly vacation rentals in Wailea, HI

Bring your pet along with stays that welcome four-legged travelers.

9 ★ 2 reviews

Maalaea Banyans by Coldwell Banker Island Vacations

Condo, Wailea

Maalaea Banyans by Coldwell Banker Island Vacations is a condo in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Maalaea Banyans by Coldwell Banker Island Vacations

Maalaea Banyans by Coldwell Banker Island Vacations is a condo in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, free wifi, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,135.

From$249/night

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Maui Vista by Coldwell Banker Island Vacations

Condo, Wailea

Maui Vista by Coldwell Banker Island Vacations is a condo in Wailea, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Maui Vista by Coldwell Banker Island Vacations

Maui Vista by Coldwell Banker Island Vacations is a condo in Wailea, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,628.

From$190/night

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Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations

Condo, Wailea

Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations is a condo in Wailea, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations

Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations is a condo in Wailea, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, gym, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,440.

From$279/night

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Wailea Elua by Coldwell Banker Island Vacations

Condo, Wailea

Wailea Elua by Coldwell Banker Island Vacations is a condo in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Wailea Elua by Coldwell Banker Island Vacations

Wailea Elua by Coldwell Banker Island Vacations is a condo in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, free wifi, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,578.

From$705/night

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Vacation rentals with a pool in Wailea, HI

Add a pool to the search when you want an easy place to cool off between outings.

9.4 ★ 110 reviews

Makena Surf - CoralTree Residence Collection

Condo, Wailea

Makena Surf - CoralTree Residence Collection is a condo in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Makena Surf - CoralTree Residence Collection

Makena Surf - CoralTree Residence Collection is a condo in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, free wifi, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,337.

From$794/night

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Maui Vista 2422

Apartment, Wailea

Maui Vista 2422 is a apartment in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Maui Vista 2422

Maui Vista 2422 is a apartment in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and ourdoor pool.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,465.

From$222/night

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Maui Vista 1114

Apartment, Wailea

Maui Vista 1114 is a apartment in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Maui Vista 1114

Maui Vista 1114 is a apartment in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and ourdoor pool.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,665.

From$139/night

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Maui Vista 1121

Apartment, Wailea

Maui Vista 1121 is a apartment in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Maui Vista 1121

Maui Vista 1121 is a apartment in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and ourdoor pool.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,760.

From$150/night

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Vacation rentals with parking in Wailea, HI

Find vacation rentals that make arriving by car easier.

Maui-LICIOUS by the Beach

Apartment, Wailea

Maui-LICIOUS by the Beach is a apartment in Wailea, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Maui-LICIOUS by the Beach

Maui-LICIOUS by the Beach is a apartment in Wailea, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,730.

From$300/night

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South Maui 1 BR Guest Suite - Kamaole Beach Area

Apartment, Wailea

South Maui 1 BR Guest Suite - Kamaole Beach Area is a apartment in Wailea, with easy beach access, parking, and room for a group. This stay gives travelers a comfortable base for exploring…

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About South Maui 1 BR Guest Suite - Kamaole Beach Area

South Maui 1 BR Guest Suite - Kamaole Beach Area is a apartment in Wailea, with easy beach access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,167.

From$238/night

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Koa Resort 4I

Holiday Home, Wailea

Koa Resort 4I is a holiday home in Wailea, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Koa Resort 4I

Koa Resort 4I is a holiday home in Wailea, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,262.

From$318/night

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Pacific Shores B-409 - Beautifully Renovated Ocean View, 2 BD / 2 BA, Split AC!

Apartment, Wailea

Pacific Shores B-409 - Beautifully Renovated Ocean View, 2 BD / 2 BA, Split AC! is a apartment in Wailea, with easy beach access and parking. This stay gives travelers a comfortable base…

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About Pacific Shores B-409 - Beautifully Renovated Ocean View, 2 BD / 2 BA, Split AC!

Pacific Shores B-409 - Beautifully Renovated Ocean View, 2 BD / 2 BA, Split AC! is a apartment in Wailea, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: parking, onsite parking, washer, and dryer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,048.

From$193/night

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