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Discover house sitting in Wailea

Stay in wonderful places by house sitting and caring for cute pets.

31 house sits in Wailea, HI, US

Looking for pet sitters in Wailea?

House sit in Honoka‘a, HI, US
Last minute
House sit pet parent - Waipio Valley dog retreat

Waipio Valley dog retreat

from 15 October 2026 to 19 October 2026 · 4 nights+ 1 more

Honoka‘a, HI, US

  • 4 dogs
House sit in East Honolulu, HI, US
New
House sit pet parent - Beautiful Hawaiian Home and Two Sweet Pups Await You!

Beautiful Hawaiian Home and Two Sweet Pups Await You!

from 18 December 2026 to 21 December 2026 · 3 nights

East Honolulu, HI, US

  • 1 dog
House sit in Kailua, HI, US
New
House sit pet parent - Beachside Stay in Kailua with Two Cozy Doggos

Beachside Stay in Kailua with Two Cozy Doggos

from 26 October 2026 to 11 November 2026 · 16 nights

Kailua, HI, US

  • 2 dogs

Sits in Wailea, Hawaii, US you've just missed

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House sit in Wailea-Makena, HI, US
House sit pet parent - Enjoy Maui Paradise with two Sweet Kitties

Enjoy Maui Paradise with two Sweet Kitties

Wailea-Makena, HI, US

  • 2 cats
  • poultry
House sit in Kīhei, HI, US
House sit pet parent - Lovely Maui, Hi.

Lovely Maui, Hi.

Kīhei, HI, US

House sit in Kīhei, HI, US
House sit pet parent - House by the beach with five adorable dogs.

House by the beach with five adorable dogs.

Kīhei, HI, US

  • 9 or more pets
House sit in Kīhei, HI, US
House sit pet parent - Enjoy Maui, Hawaii

Enjoy Maui, Hawaii

Kīhei, HI, US

  • 1 dog
House sit in Kīhei, HI, US
House sit pet parent - Gorgeous Maui snorkel beach, big quiet home with sweet older Collie, ocean views

Gorgeous Maui snorkel beach, big quiet home with sweet older Collie, ocean views

Kīhei, HI, US

  • 1 dog
House sit in Kīhei, HI, US
House sit pet parent - Stay at our Maui Beach Bungalow.

Stay at our Maui Beach Bungalow.

Kīhei, HI, US

  • 1 dog
House sit in Kīhei, HI, US
House sit pet parent - South Kihei, Maui.  2 Lab dogs

South Kihei, Maui. 2 Lab dogs

Kīhei, HI, US

  • 2 dogs
House sit in Kīhei, HI, US
House sit pet parent - Jeremy and Sugarbug (with Vegan parents) are looking for a vegan kitty sitter

Jeremy and Sugarbug (with Vegan parents) are looking for a vegan kitty sitter

Kīhei, HI, US

  • 1 cat
  • fish
House sit in Kīhei, HI, US
House sit pet parent - Welcome to Bodhi and Skittle's Casa on Maui

Welcome to Bodhi and Skittle's Casa on Maui

Kīhei, HI, US

  • 1 dog
  1. 1
  2. 2
  3. 3

Why you'll love pet and house sitting in Wailea, HI

An illustration of a cat laying on his pet bedForget hotel rooms

From home comforts to the calming company of pets, house sitting offers so much more.

An illustration of a glowing green heartIt feels good to give

Explore new places while making a difference to the lives of pets and people along the way.

An illustration of a house with a tree in the foregroundA new perspective

You don’t have to travel far. With pet and house sitting, you can find a world of adventures just around the corner.

An illustration of three coins with paws in them

A win-win without money

On house and pet sits, you’ll provide home and pet care in return for a place to stay on your travels. An annual plan unlocks unlimited access to sits, making it an affordable and fulfilling way to travel.

Find out more about memberships
“

I am so blessed to have this experience and to be able to have a companion by my side the entire time. I’m forever grateful for the opportunity TrustedHousesitters provides! This is truly life changing.

Adelia, sitter member from Bath, UK

Popular pet sitting and house sitting destinations

Feel safe, secure and supported

An illustration of a speech balloon with five stars on itRead feedback from sitters

Want to know if a house sit is right for you? Look for feedback previous sitters have left on the pet parent's listing.

An illustration of stacked documentsHome & Contents Plan

House sit in homes with peace of mind they’re covered at no extra cost to you or the pet parent.

An illustration of a dog sniffing the air24/7 Vet Advice Line

With a free direct line to a dedicated team of veterinary nurses, you can quickly clear up any pet queries.

Ready to start your Wailea house sitting adventure?

Join our worldwide community and start your membership today.

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Wailea house sitting FAQs

All that’s exchanged between our sitters and pet parents is trust - sitters get to stay in cool locations near and far, caring for pets with a place to stay in return. And with no money passing hands, we’re certain everybody’s here for the same reasons: their never-ending love for pets and travel.

With an annual sitter membership, animal lovers like you can explore the world and enjoy unique stays in exchange for pet care. Live like a local, care for adorable pets, and provide pet parents with peace of mind while they’re away. Apply for as many sits as you like and get ready for meaningful connections and unforgettable adventures.

Choose your membership plan and create a profile that stands out from the pack - include clear photos, relevant experience, and references (these don’t have to be from previous house sits). Next, set up a saved search to be the first to find out when house sitting opportunities in Wailea become available for your chosen dates. Once you’ve found the ideal sit, write a personalized message to the pet parents explaining why you're the perfect person for their furry friend! Find out more with 10 tips on how to become a house sitter.

Your number one priority when house sitting in Wailea will be taking care of the pets. Daily walks, mealtimes, and lots of cuddles will be top of the agenda as most house sits include a pet. Aside from this, house sitters in Wailea need to keep the home clean and tidy and send regular updates to the pet parents about their precious pet pals.

At TrustedHousesitters, our members are driven by a genuine love of pets, not money. They exchange loving pet care for a place to stay on their travels, gaining a wealth of experiences and memories to last a lifetime.

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