Vacation rentals in Maalaea, HI

Best Vacation rentals and Airbnb offers in Maalaea, HI

Oceanfront 3rd Floor Unit at Maalaea Kai Complex

Condo, Maalaea

Oceanfront 3rd Floor Unit at Maalaea Kai Complex is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Oceanfront 3rd Floor Unit at Maalaea Kai Complex

Oceanfront 3rd Floor Unit at Maalaea Kai Complex is a condo in Maalaea, 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 $1,465.

From$108/night

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Scenic 2BR Retreat Near Maalaea's Pristine Waters

Condo, Maalaea

Scenic 2BR Retreat Near Maalaea's Pristine Waters is a condo in Maalaea, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Scenic 2BR Retreat Near Maalaea's Pristine Waters

Scenic 2BR Retreat Near Maalaea's Pristine Waters is a condo in Maalaea, with pool 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,924.

From$140/night

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Wake to Haleakalā Sunrises and Endless Ocean Views

Condo, Maalaea

Wake to Haleakalā Sunrises and Endless Ocean Views is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Wake to Haleakalā Sunrises and Endless Ocean Views

Wake to Haleakalā Sunrises and Endless Ocean Views is a condo in Maalaea, 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 $1,814.

From$140/night

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Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool.

Condo, Maalaea

Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool. is a condo in Maalaea, with pool access, easy beach access, and parking. This stay gives…

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About Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool.

Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool. is a condo in Maalaea, 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 $1,755.

From$153/night

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Browse Vacation Rentals with a Pool in Maalaea, HI

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

Kealia Resort 608 Oceanfront Complex, Ocean View from Lanai

Condo, Maalaea

Kealia Resort 608 Oceanfront Complex, Ocean View from Lanai is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Kealia Resort 608 Oceanfront Complex, Ocean View from Lanai

Kealia Resort 608 Oceanfront Complex, Ocean View from Lanai is a condo in Maalaea, 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 $1,555.

From$135/night

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A Slice of Paradise in Oceanfront Condo (Island Sands)

Condo, Maalaea

A Slice of Paradise in Oceanfront Condo (Island Sands) is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About A Slice of Paradise in Oceanfront Condo (Island Sands)

A Slice of Paradise in Oceanfront Condo (Island Sands) is a condo in Maalaea, 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 $1,896.

From$180/night

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Ma'alaea studio just a few steps from the ocean, beach, and harbor.

Condo, Maalaea

Ma'alaea studio just a few steps from the ocean, beach, and harbor. is a condo in Maalaea, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Ma'alaea studio just a few steps from the ocean, beach, and harbor.

Ma'alaea studio just a few steps from the ocean, beach, and harbor. is a condo in Maalaea, 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 $1,991.

From$185/night

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Milowai 302 Oceanfront 2BD w Ocean Views Whale Watch

Condo, Maalaea

Milowai 302 Oceanfront 2BD w Ocean Views Whale Watch is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Milowai 302 Oceanfront 2BD w Ocean Views Whale Watch

Milowai 302 Oceanfront 2BD w Ocean Views Whale Watch is a condo in Maalaea, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,422.

From$186/night

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Best Maalaea, HI vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Budget Downtown Studio C w/European Twin Bunk Beds, AC, WIFI & free Streamers!

Apartment, Maalaea

Budget Downtown Studio C w/European Twin Bunk Beds, AC, WIFI & free Streamers! is a apartment in Maalaea, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Budget Downtown Studio C w/European Twin Bunk Beds, AC, WIFI & free Streamers!

Budget Downtown Studio C w/European Twin Bunk Beds, AC, WIFI & free Streamers! is a apartment in Maalaea, with 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $845.

From$95/night

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Budget Downtown Studio-F Queen, AC, WIFI & 4 free Streamers!

Apartment, Maalaea

Budget Downtown Studio-F Queen, AC, WIFI & 4 free Streamers! is a apartment in Maalaea, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Budget Downtown Studio-F Queen, AC, WIFI & 4 free Streamers!

Budget Downtown Studio-F Queen, AC, WIFI & 4 free Streamers! is a apartment in Maalaea, with 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 $845.

From$95/night

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Best Oceanfront Value in Kihei - Kealia Resort!

Condo, Maalaea

Best Oceanfront Value in Kihei - Kealia Resort! is a condo in Maalaea, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Best Oceanfront Value in Kihei - Kealia Resort!

Best Oceanfront Value in Kihei - Kealia Resort! is a condo in Maalaea, 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, beachfront, beach front, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,512.

From$141/night

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Maalaea Kai 311: Direct Ocean Front, Couples Retreat, Incredible Views, Split AC

Condo, Maalaea

Maalaea Kai 311: Direct Ocean Front, Couples Retreat, Incredible Views, Split AC is a condo in Maalaea, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Maalaea Kai 311: Direct Ocean Front, Couples Retreat, Incredible Views, Split AC

Maalaea Kai 311: Direct Ocean Front, Couples Retreat, Incredible Views, Split AC is a condo in Maalaea, 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, parking, onsite parking, accessible, and elevator.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,966.

From$191/night

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Best Pet-Friendly Vacation Rentals in Maalaea, HI

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

Robbins Estate

Guest House, Maalaea

Robbins Estate is a guest house in Maalaea, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Robbins Estate

Robbins Estate is a guest house in Maalaea, with pet-friendly space and 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $873.

From$94/night

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Maui Vista by Coldwell Banker Island Vacations

Condo, Maalaea

Maui Vista by Coldwell Banker Island Vacations is a condo in Maalaea, 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 Maalaea, 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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Beautiful, Luxury Oceanfront Condo- Great View, A/C, Wi-Fi, Central Location

Condo, Maalaea

Beautiful, Luxury Oceanfront Condo- Great View, A/C, Wi-Fi, Central Location is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Beautiful, Luxury Oceanfront Condo- Great View, A/C, Wi-Fi, Central Location

Beautiful, Luxury Oceanfront Condo- Great View, A/C, Wi-Fi, Central Location is a condo in Maalaea, 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 $2,467.

From$242/night

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BEAUTIFUL OCEANFRONT CONDO* EXCELLENT VIEW* PERFECT LOCATION & A/C

Condo, Maalaea

BEAUTIFUL OCEANFRONT CONDO* EXCELLENT VIEW* PERFECT LOCATION & A/C is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About BEAUTIFUL OCEANFRONT CONDO* EXCELLENT VIEW* PERFECT LOCATION & A/C

BEAUTIFUL OCEANFRONT CONDO* EXCELLENT VIEW* PERFECT LOCATION & A/C is a condo in Maalaea, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,713.

From$250/night

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Best Maalaea, HI vacation rentals with a kitchen

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

Kealia Resort 304 - Stunning Ocean Views from Both Bedrooms - Beachfront Gem!

Condo, Maalaea

Kealia Resort 304 - Stunning Ocean Views from Both Bedrooms - Beachfront Gem! is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Kealia Resort 304 - Stunning Ocean Views from Both Bedrooms - Beachfront Gem!

Kealia Resort 304 - Stunning Ocean Views from Both Bedrooms - Beachfront Gem! is a condo in Maalaea, 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 $2,260.

From$179/night

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Island Sands 500, Steps from the Beach with Ocean Views and Spacious Lanai & AC

Condo, Maalaea

Island Sands 500, Steps from the Beach with Ocean Views and Spacious Lanai & AC is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Island Sands 500, Steps from the Beach with Ocean Views and Spacious Lanai & AC

Island Sands 500, Steps from the Beach with Ocean Views and Spacious Lanai & AC is a condo in Maalaea, 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, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,196.

From$191/night

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Where Oceans Whisper Maalaea Oceanfront Condo Lanai Ocean Views and Pool

Condo, Maalaea

Where Oceans Whisper Maalaea Oceanfront Condo Lanai Ocean Views and Pool is a condo in Maalaea, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Where Oceans Whisper Maalaea Oceanfront Condo Lanai Ocean Views and Pool

Where Oceans Whisper Maalaea Oceanfront Condo Lanai Ocean Views and Pool is a condo in Maalaea, 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 $1,987.

From$193/night

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Beautiful Oceanfront Condo, Huge Views near Harbor, AC!

Condo, Maalaea

Beautiful Oceanfront Condo, Huge Views near Harbor, AC! is a condo in Maalaea, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About Beautiful Oceanfront Condo, Huge Views near Harbor, AC!

Beautiful Oceanfront Condo, Huge Views near Harbor, AC! is a condo in Maalaea, 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 $2,346.

From$199/night

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Our Favorite Family-Friendly Vacation Rentals in Maalaea, HI

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

1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!

Cottage, Maalaea

1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town! is a cottage in Maalaea, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About 1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town!

1BR Wailuku House; Renovated Plantation Home; Walk into Wailuku Town! is a cottage in Maalaea, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,447.

From$130/night

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Cute Plantation Cottage; Walk into Wailuku Town; Central Location!

Cottage, Maalaea

Cute Plantation Cottage; Walk into Wailuku Town; Central Location! is a cottage in Maalaea, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cute Plantation Cottage; Walk into Wailuku Town; Central Location!

Cute Plantation Cottage; Walk into Wailuku Town; Central Location! is a cottage in Maalaea, with 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,447.

From$130/night

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Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

Cottage, Maalaea

Newly Renovated Modern Cottage: Walk into Historic Wailuku Town! is a cottage in Maalaea, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Newly Renovated Modern Cottage: Walk into Historic Wailuku Town!

Newly Renovated Modern Cottage: Walk into Historic Wailuku Town! is a cottage in Maalaea, with 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,747.

From$169/night

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

Condo, Maalaea

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

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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 Maalaea, 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 $2,484.

From$276/night

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