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Cost of wintering in Hawaii?
Old 01-14-2019, 05:19 AM   #1
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Cost of wintering in Hawaii?

I know there's at least a couple people here who winter in Hawaii. Just wondering what it would cost ballpark? I've been to Hawaii 5 times or so but not in several years. Always rented a condo for the two weeks and it was actually pretty affordable. I can't seem to find much on long term rentals, though.
Also, what did you do for a car? I almost think it would be better to buy something and sell it before you leave then rent for 4 months?
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Old 01-14-2019, 05:32 AM   #2
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I donít know anything about long term rentals in Hawaii, but some snowbirds buy cars from Carmax at the beginning of winter and sell them back to Carmax at the end.
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Old 01-14-2019, 12:02 PM   #3
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Originally Posted by garyt View Post
I know there's at least a couple people here who winter in Hawaii. Just wondering what it would cost ballpark? I've been to Hawaii 5 times or so but not in several years. Always rented a condo for the two weeks and it was actually pretty affordable. I can't seem to find much on long term rentals, though.
Also, what did you do for a car? I almost think it would be better to buy something and sell it before you leave then rent for 4 months?

I shipped my truck $2k cost from midwest, sold wifes here and bought a "maui beach cruiser' aka $4,000 honda civic with a tired engine. I sold both the truck and car a year after we moved to come back to mainland for job opportunities.


There is strong demand for housing on Hawaii at least there was on Maui. Many transplants ended up spending money on hotels and then ended up in less desirable housing in the end. You are all stacked up on each other to enjoy paradise together so there are no 2 acre plots...very cozy on the islands, everyone lives right next to each other.
I paid $2300/month for a 1300sq ft 3br in an upper middle class neighborhood. I also rented a room from a women for a couple months for $1200/month that was on the beach but again no privacy...like really no privacy you need to be comfortable with each other living on top of each other.



Bring as little over to the island as humanly possible, there is only 1 landfill and the natives do NOT like wasteful transplants or anyone for that matter.



Best fruits and vegetables I've ever tasted over there.



DW and I plan to ER there in 13 years. We will attempt to rent a 3br condo or SFH 'ohana' for 3 to 4 months but plan to pay extra for month to month which is next to impossible to find. I'd almost plan on breaking a year lease each year unless you can work it out with the landlord.



I worked it out with my landlord early enough that she didn't keep all of my damage deposit. First and last months rent is typical.



What else...oh get used to living with cock roaches, centipedes and geckos. Nobody I knew DIDN'T have them in there house. Outdoor living!



I moved there with 2 16 x 20 totes and shipped the truck empty, matson shipping doesn't allow anything in vehicles during shipment. Saltwater journey rusted my chrome bed rails even after aggressively waxing all metal with Collonites airplane wax before the journey...it's a rough journey by sea!


Miss it soo much, had 280degree panoramic walk-around lanai ocean views, lived on the ocean for a while and the office had bi-coastal views. Paradise!
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Old 01-14-2019, 01:09 PM   #4
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Well gosh. I just checked Craigslist, out of curiosity, to see how much the rentals are in HI. I guess that living in an overpriced metro area (SF Bay Area) helps a lot, because apartment rentals seem to be significantly cheaper than Oakland, CA where I currently live. (I think I'm fairly good at spotting the scam ads too.)


Hmmmm.........
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Old 01-14-2019, 10:26 PM   #5
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We live on 2 acres in Kona on the big island. Every island is different and the big island is less crowded and more affordable in my opinion. Used cars are expensive. It cost us $1000 to ship cars here (Seattle or Long Beach to Hilo) and $800 when we decided to ship one back. Costco is good for most grocery items and gas. Airbnb will offer discounts on long term rentals for a lot of places. Some things are just expensive but, in my opinion, it’s all worth it to be here
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Old 01-14-2019, 10:40 PM   #6
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Originally Posted by garyt View Post
I know there's at least a couple people here who winter in Hawaii. Just wondering what it would cost ballpark? I've been to Hawaii 5 times or so but not in several years. Always rented a condo for the two weeks and it was actually pretty affordable. I can't seem to find much on long term rentals, though.
Also, what did you do for a car? I almost think it would be better to buy something and sell it before you leave then rent for 4 months?

I am currently wintering in Hawaii..... Costs vary widely depending on your tastes.... Use VRBO for info on long term rentals... Figure around $150 a night for Long term Term. About $1200 a Month for renting a car... I can't imagine the hassle of buying and selling one, but that's just me.... I want to relax and go fishing... So for 3 months figure around $14 Grand for Renting a Place and $3,600 for a Car....
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Old 01-14-2019, 11:25 PM   #7
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I'm wondering about a house swap for a season. We have a 'theme' home; log house within an hour's drive of several major ski resorts without having to deal with all that snow, below the snow line. Big house with an attic studio with it's own kitchen, bath and living room. (shared entry). A swap, including cars and there's a hot tub and lots of other toys. All I want is a quiet place within 10 minute walk to the ocean where I can fish and snorkel, read a book and drink POG. Oh, and I don't want to be bothered!
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Old 01-15-2019, 01:02 AM   #8
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Great thread. Thanks to the OP for starting this. Maybe DH & I should try this instead of Caribbean or S FL.
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Old 01-15-2019, 04:42 AM   #9
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Originally Posted by Major Tom View Post
Well gosh. I just checked Craigslist, out of curiosity, to see how much the rentals are in HI. I guess that living in an overpriced metro area (SF Bay Area) helps a lot, because apartment rentals seem to be significantly cheaper than Oakland, CA where I currently live. (I think I'm fairly good at spotting the scam ads too.)


Hmmmm.........
Thanks, never thought of craigslist
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Old 01-15-2019, 04:44 AM   #10
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I am currently wintering in Hawaii..... Costs vary widely depending on your tastes.... Use VRBO for info on long term rentals... Figure around $150 a night for Long term Term. About $1200 a Month for renting a car... I can't imagine the hassle of buying and selling one, but that's just me.... I want to relax and go fishing... So for 3 months figure around $14 Grand for Renting a Place and $3,600 for a Car....
I was thinking about $20K for a winter, but hoping it would be less.It would be a once in a lifetime thing.
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Old 01-15-2019, 06:04 AM   #11
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DW and I spent last February on The Big Island...we rented two weeks on the Hilo side, and two weeks on the Kona side. I think expenses vary considerably depending upon which island, and where on the island you stay.
I rented a car out of the Kona airport for the month, and I think it cost me around 2K..I found the lodgings on VRBO. They were both little "cottages" on the same property that the owners lived on. On the Hilo side (more agricultural side) it was on a lychee nut farm. It was not fancy, but it had everything we needed, and was beautiful. Lodging cost us around $5500 for the month.
We cooked most of our breakfasts and dinners, and ate out for lunch a lot. I ate a lot of poke. It was great.
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