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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New Listing! Lahaina Shores 309: Oceanfront Studio - Olowalu, HI

New Listing! Lahaina Shores 309: Oceanfront Studio

Apartment, Olowalu

New Listing! Lahaina Shores 309: Oceanfront Studio is a apartment in Olowalu, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

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About New Listing! Lahaina Shores 309: Oceanfront Studio

New Listing! Lahaina Shores 309: Oceanfront Studio is a apartment in Olowalu, 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 $1,479.

From$120/night
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Browse Waterfront Vacation Rentals in Olowalu, HI

Discover vacation rentals close to the coast, water, and beach areas around Olowalu, HI.

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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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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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.

Wake to Haleakalā Sunrises and Endless Ocean Views - Olowalu, HI

Wake to Haleakalā Sunrises and Endless Ocean Views

Condo, Olowalu

Wake to Haleakalā Sunrises and Endless Ocean Views 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 Wake to Haleakalā Sunrises and Endless Ocean Views

Wake to Haleakalā Sunrises and Endless Ocean 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, 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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Relax in Maalaea's tropical charm with ocean views - Olowalu, HI

Relax in Maalaea's tropical charm with ocean views

Condo, Olowalu

Relax in Maalaea's tropical charm with ocean views 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 Relax in Maalaea's tropical charm with ocean views

Relax in Maalaea's tropical charm with ocean 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,970.

From$143/night
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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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Ma'alaea Banyans Unit 209 - Direct Oceanfront View - Split AC in Living Room and Bedroom - Olowalu, HI

Ma'alaea Banyans Unit 209 - Direct Oceanfront View - Split AC in Living Room and Bedroom

Condo, Olowalu

Ma'alaea Banyans Unit 209 - Direct Oceanfront View - Split AC in Living Room and Bedroom is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives…

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About Ma'alaea Banyans Unit 209 - Direct Oceanfront View - Split AC in Living Room and Bedroom

Ma'alaea Banyans Unit 209 - Direct Oceanfront View - Split AC in Living Room and Bedroom 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 $1,752.

From$151/night
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Best Olowalu, HI vacation rentals with parking

Find vacation rentals that make arriving by car easier.

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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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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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.

Celebrate in style with stunning Oceanfront views - Olowalu, HI

Celebrate in style with stunning Oceanfront views

Condo, Olowalu

Celebrate in style with stunning Oceanfront views 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 Celebrate in style with stunning Oceanfront views

Celebrate in style with stunning Oceanfront 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,139.

From$159/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…

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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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Oceanfront condo with pool and 6-mile beach access summer deals - Olowalu, HI

Oceanfront condo with pool and 6-mile beach access summer deals

Condo, Olowalu

Oceanfront condo with pool and 6-mile beach access summer deals is a condo in Olowalu, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Oceanfront condo with pool and 6-mile beach access summer deals

Oceanfront condo with pool and 6-mile beach access summer deals 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,867.

From$160/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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