Vacation rentals in Wailea, HI

200 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Wailea, HI

Budget Friendly Condo Overlooking the Pool - Wailea, HI

Budget Friendly Condo Overlooking the Pool

Condo, Wailea

Budget Friendly Condo Overlooking the Pool is a condo in Wailea, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Budget Friendly Condo Overlooking the Pool

Budget Friendly Condo Overlooking the Pool 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: free cancellation, pool, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,477.

From$103/night
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Maui Vista 3-102 - Updated, Ground Level, Steps to the Pool, Walk to Everything! - Wailea, HI

Maui Vista 3-102 - Updated, Ground Level, Steps to the Pool, Walk to Everything!

Condo, Wailea

Maui Vista 3-102 - Updated, Ground Level, Steps to the Pool, Walk to Everything! is a condo in Wailea, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Maui Vista 3-102 - Updated, Ground Level, Steps to the Pool, Walk to Everything!

Maui Vista 3-102 - Updated, Ground Level, Steps to the Pool, Walk to Everything! is a condo in Wailea, with pool access, parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,501.

From$115/night
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Maui Vista 3214 Kihei condo w/ 3 pools and free parking, summer deal - Wailea, HI

Maui Vista 3214 Kihei condo w/ 3 pools and free parking, summer deal

Condo, Wailea

Maui Vista 3214 Kihei condo w/ 3 pools and free parking, summer deal is a condo in Wailea, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Maui Vista 3214 Kihei condo w/ 3 pools and free parking, summer deal

Maui Vista 3214 Kihei condo w/ 3 pools and free parking, summer deal is a condo in Wailea, with pool access, parking, 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,469.

From$120/night
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Maui Vista 2207 - Wailea, HI

Maui Vista 2207

Apartment, Wailea

Maui Vista 2207 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 2207

Maui Vista 2207 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,523.

From$123/night
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Browse 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.

Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing! - Wailea, HI

Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!

Condo, Wailea

Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing! is a condo in Wailea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!

Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing! 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, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,165.

From$204/night
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Wailea Serenity - 2BD - Private, Quiet; the tropic - Wailea, HI

Wailea Serenity - 2BD - Private, Quiet; the tropic

Condo, Wailea

Wailea Serenity - 2BD - Private, Quiet; the tropic is a condo in Wailea, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Wailea Serenity - 2BD - Private, Quiet; the tropic

Wailea Serenity - 2BD - Private, Quiet; the tropic is a condo in Wailea, with pool access, kitchen access, and a quieter setting. 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, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,287.

From$204/night
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Grand Champions #48 Stunning 180 Degree Ocean Views Top Floor Paradise Home. - Wailea, HI

Grand Champions #48 Stunning 180 Degree Ocean Views Top Floor Paradise Home.

Condo, Wailea

Grand Champions #48 Stunning 180 Degree Ocean Views Top Floor Paradise Home. is a condo in Wailea, with pool access and easy beach access. This stay gives travelers a comfortable base for…

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About Grand Champions #48 Stunning 180 Degree Ocean Views Top Floor Paradise Home.

Grand Champions #48 Stunning 180 Degree Ocean Views Top Floor Paradise Home. is a condo 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,447.

From$214/night
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Summer Deal Wailea Condo with Golf Course Views Pool and Hot Tub - Wailea, HI

Summer Deal Wailea Condo with Golf Course Views Pool and Hot Tub

Condo, Wailea

Summer Deal Wailea Condo with Golf Course Views Pool and Hot Tub is a condo in Wailea, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Summer Deal Wailea Condo with Golf Course Views Pool and Hot Tub

Summer Deal Wailea Condo with Golf Course Views Pool and Hot Tub 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,378.

From$214/night
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Best Wailea, HI vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Escape to Paradise at the Maui Vista \"3rd Bld 1b/1b\" - Wailea, HI

Escape to Paradise at the Maui Vista \"3rd Bld 1b/1b\"

Condo, Wailea

Escape to Paradise at the Maui Vista \"3rd Bld 1b/1b\" is a condo in Wailea, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Escape to Paradise at the Maui Vista \"3rd Bld 1b/1b\"

Escape to Paradise at the Maui Vista \"3rd Bld 1b/1b\" is a condo in Wailea, with pool access, parking, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,453.

From$136/night
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Well-maintained lofted 2 Bedroom - Maui Vista 2411 - Wailea, HI

Well-maintained lofted 2 Bedroom - Maui Vista 2411

Condo, Wailea

Well-maintained lofted 2 Bedroom - Maui Vista 2411 is a condo in Wailea, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Well-maintained lofted 2 Bedroom - Maui Vista 2411

Well-maintained lofted 2 Bedroom - Maui Vista 2411 is a condo in Wailea, with pool access, parking, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,178.

From$176/night
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Near the Beach - Wailea, HI

Near the Beach

Condo, Wailea

Near the Beach is a condo 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…

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About Near the Beach

Near the Beach is a condo 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, hot tub, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,909.

From$179/night
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Best Value in MAUI NOW!!! Specials - Wailea, HI

Best Value in MAUI NOW!!! Specials

Condo, Wailea

Best Value in MAUI NOW!!! Specials is a condo in Wailea, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Best Value in MAUI NOW!!! Specials

Best Value in MAUI NOW!!! Specials is a condo in Wailea, with pool access, parking, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,935.

From$180/night
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Best Pet-Friendly Vacation Rentals in Wailea, HI

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

Maui Vista by Coldwell Banker Island Vacations - Wailea, HI

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,868.

From$148/night
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Grand Champions One Bedrooms by Coldwell Banker Island Vacations - Wailea, HI

Grand Champions One Bedrooms by Coldwell Banker Island Vacations

Condo, Wailea

Grand Champions 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 Grand Champions One Bedrooms by Coldwell Banker Island Vacations

Grand Champions 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,579.

From$203/night
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Grand Champions #50, Great Location Near Pool and Hot Tub, AC Throughout - Wailea, HI

Grand Champions #50, Great Location Near Pool and Hot Tub, AC Throughout

Condo, Wailea

Grand Champions #50, Great Location Near Pool and Hot Tub, AC Throughout is a condo in Wailea, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Grand Champions #50, Great Location Near Pool and Hot Tub, AC Throughout

Grand Champions #50, Great Location Near Pool and Hot Tub, AC Throughout 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, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,558.

From$225/night
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Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations - Wailea, HI

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, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,477.

From$278/night
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Best Wailea, HI vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Maui Vista 3218 Kihei condo steps to sand and pools, summer deal - Wailea, HI

Maui Vista 3218 Kihei condo steps to sand and pools, summer deal

Condo, Wailea

Maui Vista 3218 Kihei condo steps to sand and pools, summer deal is a condo in Wailea, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Maui Vista 3218 Kihei condo steps to sand and pools, summer deal

Maui Vista 3218 Kihei condo steps to sand and pools, summer deal 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,607.

From$137/night
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Maui Vista 3401 2BR condo w/ ocean views and 3 pools, summer deal - Wailea, HI

Maui Vista 3401 2BR condo w/ ocean views and 3 pools, summer deal

Condo, Wailea

Maui Vista 3401 2BR condo w/ ocean views and 3 pools, summer deal is a condo in Wailea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Maui Vista 3401 2BR condo w/ ocean views and 3 pools, summer deal

Maui Vista 3401 2BR condo w/ ocean views and 3 pools, summer deal 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,691.

From$139/night
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Cozy condo with a view of famous Kamaole Beach II - Wailea, HI

Cozy condo with a view of famous Kamaole Beach II

Condo, Wailea

Cozy condo with a view of famous Kamaole Beach II 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 Cozy condo with a view of famous Kamaole Beach II

Cozy condo with a view of famous Kamaole Beach II 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: free cancellation, pool, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,694.

From$165/night
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Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112 - Wailea, HI

Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112

Condo, Wailea

Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112 is a condo in Wailea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112

Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,691.

From$222/night
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