Vacation rentals in Wailea-Makena, HI

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in Wailea-Makena, HI

Maui Vista by Coldwell Banker Island Vacations - Wailea-Makena, HI

Maui Vista by Coldwell Banker Island Vacations

Condo, Wailea-Makena

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

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About Maui Vista by Coldwell Banker Island Vacations

Maui Vista by Coldwell Banker Island Vacations is a condo in Wailea-Makena, 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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Island escape, beachside bliss - Wailea-Makena, HI

Island escape, beachside bliss

Condo, Wailea-Makena

Island escape, beachside bliss is a condo in Wailea-Makena, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Island escape, beachside bliss

Island escape, beachside bliss is a condo in Wailea-Makena, 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 free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,120.

From$160/night
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Soothing 1-bedroom condo with AC in lovely Kihei - Wailea-Makena, HI

Soothing 1-bedroom condo with AC in lovely Kihei

Condo, Wailea-Makena

Soothing 1-bedroom condo with AC in lovely Kihei is a condo in Wailea-Makena, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Soothing 1-bedroom condo with AC in lovely Kihei

Soothing 1-bedroom condo with AC in lovely Kihei is a condo in Wailea-Makena, with 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,226.

From$175/night
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Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach - Wailea-Makena, HI

Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach

Cottage, Wailea-Makena

Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach is a cottage in Wailea-Makena, with easy beach access, kitchen access, and room for a group. This stay gives travelers a…

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About Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach

Private Modern 1BR/1BA Tropical Kihei Maui Cottage by the Beach is a cottage in Wailea-Makena, with easy beach access, kitchen 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: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,245.

From$178/night
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Vacation rentals with a pool in Wailea-Makena, HI

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

Beautiful remodeled Kihei Condo next to the Beach! - Wailea-Makena, HI

Beautiful remodeled Kihei Condo next to the Beach!

Condo, Wailea-Makena

Beautiful remodeled Kihei Condo next to the Beach! is a condo in Wailea-Makena, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About Beautiful remodeled Kihei Condo next to the Beach!

Beautiful remodeled Kihei Condo next to the Beach! is a condo in Wailea-Makena, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,402.

From$200/night
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Pacific Shores B203 2 Bedroom Condo - Wailea-Makena, HI

Pacific Shores B203 2 Bedroom Condo

Condo, Wailea-Makena

Pacific Shores B203 2 Bedroom Condo is a condo in Wailea-Makena, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Pacific Shores B203 2 Bedroom Condo

Pacific Shores B203 2 Bedroom Condo is a condo in Wailea-Makena, 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 $3,734.

From$212/night
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Maui Banyan - 1BR Partial Ocean View - No Cleaning Fee/ Full Kitchen - Wailea-Makena, HI

Maui Banyan - 1BR Partial Ocean View - No Cleaning Fee/ Full Kitchen

Condo, Wailea-Makena

Maui Banyan - 1BR Partial Ocean View - No Cleaning Fee/ Full Kitchen is a condo in Wailea-Makena, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Maui Banyan - 1BR Partial Ocean View - No Cleaning Fee/ Full Kitchen

Maui Banyan - 1BR Partial Ocean View - No Cleaning Fee/ Full Kitchen is a condo in Wailea-Makena, 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 $1,678.

From$240/night
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Kamaole Sands, Bldg 5, Inner Courtyard, Sleeps 4 / King Bed & NEW Sofa Sleeper - Wailea-Makena, HI

Kamaole Sands, Bldg 5, Inner Courtyard, Sleeps 4 / King Bed & NEW Sofa Sleeper

Condo, Wailea-Makena

Kamaole Sands, Bldg 5, Inner Courtyard, Sleeps 4 / King Bed & NEW Sofa Sleeper is a condo in Wailea-Makena, with pool access and room for a group. This stay gives travelers a comfortable…

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About Kamaole Sands, Bldg 5, Inner Courtyard, Sleeps 4 / King Bed & NEW Sofa Sleeper

Kamaole Sands, Bldg 5, Inner Courtyard, Sleeps 4 / King Bed & NEW Sofa Sleeper is a condo in Wailea-Makena, 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 $1,696.

From$242/night
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Vacation rentals with parking in Wailea-Makena, HI

Find vacation rentals that make arriving by car easier.

Quiet & Private S. Kihei 1BR Guest Suite - 10 minute walk to Kamaole Beach II - Wailea-Makena, HI

Quiet & Private S. Kihei 1BR Guest Suite - 10 minute walk to Kamaole Beach II

Apartment, Wailea-Makena

Quiet & Private S. Kihei 1BR Guest Suite - 10 minute walk to Kamaole Beach II is a apartment in Wailea-Makena, with easy beach access, parking, and kitchen access. This stay gives travelers…

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About Quiet & Private S. Kihei 1BR Guest Suite - 10 minute walk to Kamaole Beach II

Quiet & Private S. Kihei 1BR Guest Suite - 10 minute walk to Kamaole Beach II is a apartment in Wailea-Makena, with easy beach 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,630.

From$233/night
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Near the Beach - Wailea-Makena, HI

Near the Beach

Condo, Wailea-Makena

Near the Beach is a condo in Wailea-Makena, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Near the Beach

Near the Beach is a condo in Wailea-Makena, 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 $1,632.

From$233/night
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South Maui 1 BR Guest Suite - Kamaole Beach Area - Wailea-Makena, HI

South Maui 1 BR Guest Suite - Kamaole Beach Area

Apartment, Wailea-Makena

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

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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-Makena, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,167.

From$238/night
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Well-maintained lofted 2 Bedroom - Maui Vista 2411 - Wailea-Makena, HI

Well-maintained lofted 2 Bedroom - Maui Vista 2411

Condo, Wailea-Makena

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

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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-Makena, 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 $1,873.

From$268/night
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Pet-friendly vacation rentals in Wailea-Makena, HI

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

Spacious, Great Location. Close to Beaches! - 1 bedroom condo - Pool, WiFi, AC! - Wailea-Makena, HI

Spacious, Great Location. Close to Beaches! - 1 bedroom condo - Pool, WiFi, AC!

Condo, Wailea-Makena

Spacious, Great Location. Close to Beaches! - 1 bedroom condo - Pool, WiFi, AC! is a condo in Wailea-Makena, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Spacious, Great Location. Close to Beaches! - 1 bedroom condo - Pool, WiFi, AC!

Spacious, Great Location. Close to Beaches! - 1 bedroom condo - Pool, WiFi, AC! is a condo in Wailea-Makena, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,429.

From$204/night
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REDUCED RATES!! - PRIME KIHEI LOCATION!! ACROSS FROM POPULAR KAMAOLE II Beach - Wailea-Makena, HI

REDUCED RATES!! - PRIME KIHEI LOCATION!! ACROSS FROM POPULAR KAMAOLE II Beach

Condo, Wailea-Makena

REDUCED RATES!! - PRIME KIHEI LOCATION!! ACROSS FROM POPULAR KAMAOLE II Beach is a condo in Wailea-Makena, with pool access, easy beach access, and parking. This stay gives travelers a…

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About REDUCED RATES!! - PRIME KIHEI LOCATION!! ACROSS FROM POPULAR KAMAOLE II Beach

REDUCED RATES!! - PRIME KIHEI LOCATION!! ACROSS FROM POPULAR KAMAOLE II Beach is a condo in Wailea-Makena, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,856.

From$265/night
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Beautiful 1 bedroom/2 bath condo centrally located - Wailea-Makena, HI

Beautiful 1 bedroom/2 bath condo centrally located

Condo, Wailea-Makena

Beautiful 1 bedroom/2 bath condo centrally located is a condo in Wailea-Makena, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Beautiful 1 bedroom/2 bath condo centrally located

Beautiful 1 bedroom/2 bath condo centrally located is a condo in Wailea-Makena, 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 $1,879.

From$268/night
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Conveniently located two bedroom two bath HK319 - Wailea-Makena, HI

Conveniently located two bedroom two bath HK319

Apartment, Wailea-Makena

Conveniently located two bedroom two bath HK319 is a apartment in Wailea-Makena, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Conveniently located two bedroom two bath HK319

Conveniently located two bedroom two bath HK319 is a apartment in Wailea-Makena, with parking, kitchen 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,992.

From$285/night
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Vacation rentals with a kitchen in Wailea-Makena, HI

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

Maui Vista Resort Paradise! - Wailea-Makena, HI

Maui Vista Resort Paradise!

Condo, Wailea-Makena

Maui Vista Resort Paradise! is a condo in Wailea-Makena, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Maui Vista Resort Paradise!

Maui Vista Resort Paradise! is a condo in Wailea-Makena, 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 $1,629.

From$233/night
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Pacific Shores B-409 - Beautifully Renovated Ocean View, 2 BD / 2 BA, Split AC! - Wailea-Makena, HI

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

Apartment, Wailea-Makena

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

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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-Makena, 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 $1,676.

From$239/night
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Maui Banyan Kihei condo across Charley Young Beach, summer deal - Wailea-Makena, HI

Maui Banyan Kihei condo across Charley Young Beach, summer deal

Condo, Wailea-Makena

Maui Banyan Kihei condo across Charley Young Beach, summer deal is a condo in Wailea-Makena, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Maui Banyan Kihei condo across Charley Young Beach, summer deal

Maui Banyan Kihei condo across Charley Young Beach, summer deal is a condo in Wailea-Makena, 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 $1,739.

From$248/night
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Time Beach @ Grand Van Kleef - Wailea-Makena, HI

Time Beach @ Grand Van Kleef

Condo, Wailea-Makena

Time Beach @ Grand Van Kleef is a condo in Wailea-Makena, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Time Beach @ Grand Van Kleef

Time Beach @ Grand Van Kleef is a condo in Wailea-Makena, 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 $1,813.

From$259/night
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Family-friendly vacation rentals in Wailea-Makena, HI

Plan a trip with stays that give families more room to spread out.

Colorful Kamaole Sands Condo, Kihei, with Family Friendly Pool, Steps from Beach - Wailea-Makena, HI

Colorful Kamaole Sands Condo, Kihei, with Family Friendly Pool, Steps from Beach

Condo, Wailea-Makena

Colorful Kamaole Sands Condo, Kihei, with Family Friendly Pool, Steps from Beach is a condo in Wailea-Makena, with pool access, easy beach access, and room for a group. This stay gives…

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About Colorful Kamaole Sands Condo, Kihei, with Family Friendly Pool, Steps from Beach

Colorful Kamaole Sands Condo, Kihei, with Family Friendly Pool, Steps from Beach is a condo in Wailea-Makena, with pool access, easy beach 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 $1,639.

From$234/night
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PARADISE IS CALLING-Oceanview Family Size-Resort Zoned-King Beds-No Cleaning Fee - Wailea-Makena, HI

PARADISE IS CALLING-Oceanview Family Size-Resort Zoned-King Beds-No Cleaning Fee

Condo, Wailea-Makena

PARADISE IS CALLING-Oceanview Family Size-Resort Zoned-King Beds-No Cleaning Fee is a condo in Wailea-Makena, with pool access, easy beach access, and room for a group. This stay gives…

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About PARADISE IS CALLING-Oceanview Family Size-Resort Zoned-King Beds-No Cleaning Fee

PARADISE IS CALLING-Oceanview Family Size-Resort Zoned-King Beds-No Cleaning Fee is a condo in Wailea-Makena, with pool access, easy beach 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 $2,114.

From$302/night
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Private Ocean View Cottage Overlooking Wailea - Wailea-Makena, HI

Private Ocean View Cottage Overlooking Wailea

Cottage, Wailea-Makena

Private Ocean View Cottage Overlooking Wailea is a cottage in Wailea-Makena, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Private Ocean View Cottage Overlooking Wailea

Private Ocean View Cottage Overlooking Wailea is a cottage in Wailea-Makena, with easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,174.

From$311/night
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Rainbow Deluxe - 2 BR/2 BA Cottage - Simply Wonderful! - Wailea-Makena, HI

Rainbow Deluxe - 2 BR/2 BA Cottage - Simply Wonderful!

Holiday Home, Wailea-Makena

Rainbow Deluxe - 2 BR/2 BA Cottage - Simply Wonderful! is a holiday home in Wailea-Makena, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Rainbow Deluxe - 2 BR/2 BA Cottage - Simply Wonderful!

Rainbow Deluxe - 2 BR/2 BA Cottage - Simply Wonderful! is a holiday home in Wailea-Makena, with kitchen 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,685.

From$384/night
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