Vacation rentals in Kaupo, HI

63 available vacation rental offers

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Best vacation rentals and Airbnb offers in Kaupo, HI

Luxurious Wailea Ocean Vistas - Kaupo, HI
10 ★ 7 reviews

Luxurious Wailea Ocean Vistas

Condo, Kaupo

Luxurious Wailea Ocean Vistas is a condo in Kaupo, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxurious Wailea Ocean Vistas

Luxurious Wailea Ocean Vistas is a condo in Kaupo, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,750.

From$416/night
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Grand Champions by KBM - Kaupo, HI
10 ★ 4 reviews

Grand Champions by KBM

Condo, Kaupo

Grand Champions by KBM is a condo in Kaupo, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Grand Champions by KBM

Grand Champions by KBM is a condo in Kaupo, 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: pool, free wifi, kitchen, with kitchen, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,151.

From$304/night
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Kihei Akahi D-105 by Maui Rental Group - Kaupo, HI
10 ★ 3 reviews

Kihei Akahi D-105 by Maui Rental Group

Condo, Kaupo

Kihei Akahi D-105 by Maui Rental Group is a condo in Kaupo, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Kihei Akahi D-105 by Maui Rental Group

Kihei Akahi D-105 by Maui Rental Group is a condo in Kaupo, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,062.

From$165/night
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Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations - Kaupo, HI
10 ★ 1 reviews

Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations

Condo, Kaupo

Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations is a condo in Kaupo, with pool access, easy beach access, and room for a group. This stay gives…

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About Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations

Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations is a condo in Kaupo, 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, free wifi, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,124.

From$237/night
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Pet-friendly vacation rentals in Kaupo, HI

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

Polo Beach Club Vacation Rentals - APlus Resorts - Kaupo, HI
10 ★ 2 reviews

Polo Beach Club Vacation Rentals - APlus Resorts

Condo, Kaupo

Polo Beach Club Vacation Rentals - APlus Resorts is a condo in Kaupo, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Polo Beach Club Vacation Rentals - APlus Resorts

Polo Beach Club Vacation Rentals - APlus Resorts is a condo in Kaupo, 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, with kitchen, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $7,057.

From$696/night
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Palms at Wailea Two Bedrooms - Garden View by Coldwell Banker Island Vacations - Kaupo, HI
8 ★ 1 reviews

Palms at Wailea Two Bedrooms - Garden View by Coldwell Banker Island Vacations

Condo, Kaupo

Palms at Wailea Two Bedrooms - Garden View by Coldwell Banker Island Vacations is a condo in Kaupo, with pool access and room for a group. This stay gives travelers a comfortable base for…

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About Palms at Wailea Two Bedrooms - Garden View by Coldwell Banker Island Vacations

Palms at Wailea Two Bedrooms - Garden View by Coldwell Banker Island Vacations is a condo in Kaupo, 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, free wifi, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $5,901.

From$562/night
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Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations - Kaupo, HI

Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations

Condo, Kaupo

Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations is a condo in Kaupo, 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 Kaupo, 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, gym, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,598.

From$298/night
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Wailea Ekahi One Bedrooms - Ocean View by Coldwell Banker Island Vacations - Kaupo, HI

Wailea Ekahi One Bedrooms - Ocean View by Coldwell Banker Island Vacations

Condo, Kaupo

Wailea Ekahi One Bedrooms - Ocean View by Coldwell Banker Island Vacations is a condo in Kaupo, with pool access, easy beach access, and room for a group. This stay gives travelers a…

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About Wailea Ekahi One Bedrooms - Ocean View by Coldwell Banker Island Vacations

Wailea Ekahi One Bedrooms - Ocean View by Coldwell Banker Island Vacations is a condo in Kaupo, 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, free wifi, gym, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $5,285.

From$495/night
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Vacation rentals with a pool in Kaupo, HI

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

Makena Surf - CoralTree Residence Collection - Kaupo, HI
9.4 ★ 110 reviews

Makena Surf - CoralTree Residence Collection

Condo, Kaupo

Makena Surf - CoralTree Residence Collection is a condo in Kaupo, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Makena Surf - CoralTree Residence Collection

Makena Surf - CoralTree Residence Collection is a condo in Kaupo, 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, free wifi, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $7,129.

From$771/night
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Refined Resort Wailea Oceanview Vistas - Kaupo, HI
9 ★ 2 reviews

Refined Resort Wailea Oceanview Vistas

Apartment, Kaupo

Refined Resort Wailea Oceanview Vistas is a apartment in Kaupo, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Refined Resort Wailea Oceanview Vistas

Refined Resort Wailea Oceanview Vistas is a apartment in Kaupo, 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, free wifi, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,699.

From$406/night
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Plumeria Room on a Lush Farm on Maui's North Shore - Kaupo, HI

Plumeria Room on a Lush Farm on Maui's North Shore

Farmhouse, Kaupo

Plumeria Room on a Lush Farm on Maui's North Shore is a farmhouse in Kaupo, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Plumeria Room on a Lush Farm on Maui's North Shore

Plumeria Room on a Lush Farm on Maui's North Shore is a farmhouse in Kaupo, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,170.

From$259/night
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Banyan Tree B&B Retreat - Kaupo, HI

Banyan Tree B&B Retreat

B & B, Kaupo

Banyan Tree B&B Retreat is a b & b in Kaupo, with pool access, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Banyan Tree B&B Retreat

Banyan Tree B&B Retreat is a b & b in Kaupo, with pool access, parking, 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 breakfast, pool, free wifi, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,220.

From$265/night
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Vacation rentals with parking in Kaupo, HI

Find vacation rentals that make arriving by car easier.

Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views! - Kaupo, HI

Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views!

Condo, Kaupo

Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views! is a condo in Kaupo, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views!

Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views! is a condo in Kaupo, 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, living room, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,114.

From$318/night
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Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-story in Beautiful Wailea - Kaupo, HI

Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-story in Beautiful Wailea

Condo, Kaupo

Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-story in Beautiful Wailea is a condo in Kaupo, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-story in Beautiful Wailea

Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-story in Beautiful Wailea is a condo in Kaupo, 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, living room, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,196.

From$320/night
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Experience Stunning Ocean Views at Wailea Ekolu 403, Spacious, Wi-fi, Split-ac! - Kaupo, HI

Experience Stunning Ocean Views at Wailea Ekolu 403, Spacious, Wi-fi, Split-ac!

Condo, Kaupo

Experience Stunning Ocean Views at Wailea Ekolu 403, Spacious, Wi-fi, Split-ac! is a condo in Kaupo, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Experience Stunning Ocean Views at Wailea Ekolu 403, Spacious, Wi-fi, Split-ac!

Experience Stunning Ocean Views at Wailea Ekolu 403, Spacious, Wi-fi, Split-ac! is a condo in Kaupo, 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, living room, and condominium.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,245.

From$334/night
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Jasmine Suite on Lush farm in Haiku, Maui jungle - Kaupo, HI

Jasmine Suite on Lush farm in Haiku, Maui jungle

Chalet, Kaupo

Jasmine Suite on Lush farm in Haiku, Maui jungle is a chalet in Kaupo, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Jasmine Suite on Lush farm in Haiku, Maui jungle

Jasmine Suite on Lush farm in Haiku, Maui jungle is a chalet in Kaupo, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,343.

From$400/night
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