Vacation rentals in Olowalu, HI

200 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Olowalu, HI

Oceanfront 3rd Floor Unit at Maalaea Kai Complex - Olowalu, HI

Oceanfront 3rd Floor Unit at Maalaea Kai Complex

Condo, Olowalu

Oceanfront 3rd Floor Unit at Maalaea Kai Complex is a condo in Olowalu, 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 Olowalu, 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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Ground-Floor Beachfront 1BR Relax, Explore, Unwind - Olowalu, HI

Ground-Floor Beachfront 1BR Relax, Explore, Unwind

Condo, Olowalu

Ground-Floor Beachfront 1BR Relax, Explore, Unwind is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Ground-Floor Beachfront 1BR Relax, Explore, Unwind

Ground-Floor Beachfront 1BR Relax, Explore, Unwind is a condo in Olowalu, 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 $1,556.

From$113/night
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Beachfront easy living by the Ocean 1BR Haven - Olowalu, HI

Beachfront easy living by the Ocean 1BR Haven

Condo, Olowalu

Beachfront easy living by the Ocean 1BR Haven is a condo in Olowalu, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Beachfront easy living by the Ocean 1BR Haven

Beachfront easy living by the Ocean 1BR Haven is a condo in Olowalu, 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: free cancellation, free wifi, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,566.

From$114/night
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*Hono Kai A15* New Listing! New remodel! Maui condo steps to the sand! - Olowalu, HI

*Hono Kai A15* New Listing! New remodel! Maui condo steps to the sand!

Condo, Olowalu

*Hono Kai A15* New Listing! New remodel! Maui condo steps to the sand! is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About *Hono Kai A15* New Listing! New remodel! Maui condo steps to the sand!

*Hono Kai A15* New Listing! New remodel! Maui condo steps to the sand! is a condo in Olowalu, 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 $1,501.

From$124/night
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Browse Vacation Rentals with a Pool in Olowalu, HI

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

Oceanfront Ground Level 1BR Plantation Style - Olowalu, HI

Oceanfront Ground Level 1BR Plantation Style

Condo, Olowalu

Oceanfront Ground Level 1BR Plantation Style is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Oceanfront Ground Level 1BR Plantation Style

Oceanfront Ground Level 1BR Plantation Style is a condo in Olowalu, 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 $1,892.

From$144/night
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Hono Kai Resort B16 - Olowalu, HI

Hono Kai Resort B16

Apartment, Olowalu

Hono Kai Resort B16 is a apartment in Olowalu, 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 Hono Kai Resort B16

Hono Kai Resort B16 is a apartment in Olowalu, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,747.

From$153/night
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Bask, breathe, and relax. Ocean views from your 2bd - Olowalu, HI

Bask, breathe, and relax. Ocean views from your 2bd

Condo, Olowalu

Bask, breathe, and relax. Ocean views from your 2bd is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Bask, breathe, and relax. Ocean views from your 2bd

Bask, breathe, and relax. Ocean views from your 2bd is a condo in Olowalu, 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 $2,078.

From$153/night
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Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool. - Olowalu, HI

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

Condo, Olowalu

Island Sands 401 Oceanfront Condo with Ocean View. Enjoy the saltwater oceanfront swimming pool. is a condo in Olowalu, 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 Olowalu, 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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Best Olowalu, HI vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Maui Stunning Prime Ocean Front View of the Bay and Haleakala! *Maalaea Kai 212* - Olowalu, HI

Maui Stunning Prime Ocean Front View of the Bay and Haleakala! *Maalaea Kai 212*

Condo, Olowalu

Maui Stunning Prime Ocean Front View of the Bay and Haleakala! *Maalaea Kai 212* is a condo in Olowalu, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Maui Stunning Prime Ocean Front View of the Bay and Haleakala! *Maalaea Kai 212*

Maui Stunning Prime Ocean Front View of the Bay and Haleakala! *Maalaea Kai 212* is a condo in Olowalu, 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 $2,102.

From$170/night
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Lahaina Roads Suite 212 - OCEANFRONT Property gorgeous views- 1 Bed 1 Bath Condo - Olowalu, HI

Lahaina Roads Suite 212 - OCEANFRONT Property gorgeous views- 1 Bed 1 Bath Condo

Apartment, Olowalu

Lahaina Roads Suite 212 - OCEANFRONT Property gorgeous views- 1 Bed 1 Bath Condo is a apartment in Olowalu, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Lahaina Roads Suite 212 - OCEANFRONT Property gorgeous views- 1 Bed 1 Bath Condo

Lahaina Roads Suite 212 - OCEANFRONT Property gorgeous views- 1 Bed 1 Bath Condo is a apartment in Olowalu, 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 $1,935.

From$175/night
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Ma'alaea studio just a few steps from the ocean, beach, and harbor. - Olowalu, HI

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

Condo, Olowalu

Ma'alaea studio just a few steps from the ocean, beach, and harbor. is a condo in Olowalu, 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 Olowalu, 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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Kanai A Nalu 202 - Olowalu, HI

Kanai A Nalu 202

Apartment, Olowalu

Kanai A Nalu 202 is a apartment in Olowalu, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

Read more

About Kanai A Nalu 202

Kanai A Nalu 202 is a apartment in Olowalu, 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 paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,250.

From$191/night
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Best Pet-Friendly Vacation Rentals in Olowalu, HI

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

Suite Maui Paradise Condo - Olowalu, HI

Suite Maui Paradise Condo

Holiday Home, Olowalu

Suite Maui Paradise Condo is a holiday home in Olowalu, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Suite Maui Paradise Condo

Suite Maui Paradise Condo is a holiday home in Olowalu, 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 $1,942.

From$176/night
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Beautiful, Luxury Oceanfront Condo- Great View, A/C, Wi-Fi, Central Location - Olowalu, HI

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

Condo, Olowalu

Beautiful, Luxury Oceanfront Condo- Great View, A/C, Wi-Fi, Central Location is a condo in Olowalu, 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 Olowalu, 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 - Olowalu, HI

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

Condo, Olowalu

BEAUTIFUL OCEANFRONT CONDO* EXCELLENT VIEW* PERFECT LOCATION & A/C is a condo in Olowalu, 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 Olowalu, 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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2 Bed Maui Retreat with 5 miles of beach! - Olowalu, HI

2 Bed Maui Retreat with 5 miles of beach!

Apartment, Olowalu

2 Bed Maui Retreat with 5 miles of beach! is a apartment in Olowalu, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring…

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About 2 Bed Maui Retreat with 5 miles of beach!

2 Bed Maui Retreat with 5 miles of beach! is a apartment in Olowalu, with pet-friendly space, 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,802.

From$270/night
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Best Olowalu, HI vacation rentals with a kitchen

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

Breezy Maalaea Oceanfront Condo Newly Renovated Pool BBQ Near the Harbor - Olowalu, HI

Breezy Maalaea Oceanfront Condo Newly Renovated Pool BBQ Near the Harbor

Condo, Olowalu

Breezy Maalaea Oceanfront Condo Newly Renovated Pool BBQ Near the Harbor is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Breezy Maalaea Oceanfront Condo Newly Renovated Pool BBQ Near the Harbor

Breezy Maalaea Oceanfront Condo Newly Renovated Pool BBQ Near the Harbor is a condo in Olowalu, 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 $1,600.

From$155/night
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Maalaea Kai 311: Direct Ocean Front, Couples Retreat, Incredible Views, Split AC - Olowalu, HI

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

Condo, Olowalu

Maalaea Kai 311: Direct Ocean Front, Couples Retreat, Incredible Views, Split AC is a condo in Olowalu, with pool access, easy beach access, and kitchen access. 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 Olowalu, 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 $1,884.

From$158/night
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Ma'alaea Kai #102 – Oceanfront Ground-Floor Escape with AC and Tranquil Views - Olowalu, HI

Ma'alaea Kai #102 – Oceanfront Ground-Floor Escape with AC and Tranquil Views

Condo, Olowalu

Ma'alaea Kai #102 – Oceanfront Ground-Floor Escape with AC and Tranquil Views is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

Read more

About Ma'alaea Kai #102 – Oceanfront Ground-Floor Escape with AC and Tranquil Views

Ma'alaea Kai #102 – Oceanfront Ground-Floor Escape with AC and Tranquil Views is a condo in Olowalu, 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 $2,015.

From$159/night
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Spectacular View 1 Bedroom Condo right on the ocean, Lahaina: Direct from Owner - Olowalu, HI

Spectacular View 1 Bedroom Condo right on the ocean, Lahaina: Direct from Owner

Condo, Olowalu

Spectacular View 1 Bedroom Condo right on the ocean, Lahaina: Direct from Owner is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Spectacular View 1 Bedroom Condo right on the ocean, Lahaina: Direct from Owner

Spectacular View 1 Bedroom Condo right on the ocean, Lahaina: Direct from Owner is a condo in Olowalu, 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 $2,004.

From$180/night
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Our Favorite Family-Friendly Vacation Rentals in Olowalu, HI

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

Oceanfront Lahaina Retreat - Olowalu, HI

Oceanfront Lahaina Retreat

Condo, Olowalu

Oceanfront Lahaina Retreat is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Oceanfront Lahaina Retreat

Oceanfront Lahaina Retreat is a condo in Olowalu, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,503.

From$233/night
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Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Island View - Olowalu, HI

Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Island View

Condo, Olowalu

Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Island View is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Island View

Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Island View is a condo in Olowalu, 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 $3,614.

From$391/night
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Ocean View Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Family Friendly - Olowalu, HI

Ocean View Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Family Friendly

Condo, Olowalu

Ocean View Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Family Friendly is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay…

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About Ocean View Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Family Friendly

Ocean View Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Family Friendly is a condo in Olowalu, 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 $3,681.

From$391/night
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Spacious 2BR Condo On The Beach - Kids Pirate Pool - Family Friendly - Beach Gear Rentals! - Olowalu, HI

Spacious 2BR Condo On The Beach - Kids Pirate Pool - Family Friendly - Beach Gear Rentals!

Condo, Olowalu

Spacious 2BR Condo On The Beach - Kids Pirate Pool - Family Friendly - Beach Gear Rentals! is a condo in Olowalu, with pool access, easy beach access, and room for a group. This stay gives…

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About Spacious 2BR Condo On The Beach - Kids Pirate Pool - Family Friendly - Beach Gear Rentals!

Spacious 2BR Condo On The Beach - Kids Pirate Pool - Family Friendly - Beach Gear Rentals! is a condo in Olowalu, 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: pool, hot tub, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,878.

From$412/night
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