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Old 08-07-2016, 07:11 PM   #21
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+1 At least a year in advance for good places.
I am becoming less infatuated with the Keys after hearing this. Maybe the redneck Riviera would be better.
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Old 08-07-2016, 07:25 PM   #22
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I am becoming less infatuated with the Keys after hearing this. Maybe the redneck Riviera would be better.
The Keys are great. The problem with most of S.FL is that it is so nice that once folks get a place to rent they love it and just keep re-upping for the next year as they depart.

If you work at it and get a place you'd be well rewarded for years to come.

A local realtor is the best option IMHO; I'd avoid Craig's and the like unless you really know the areas; there can be some really crappy places and a general rule is you'll not find any bargains. You'll get what you pay for.

There's still time but by mid-September your options get very narrow.
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Old 08-08-2016, 04:19 AM   #23
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We rented out our condo in Bonita Springs (north of Naples) on VRBO when we owned it. (We now have one in Ft. Myers). Typically, we were contacted by potential renters about 8-9 months before winter. We had a good experience on VRBO as landlords. Be aware that most people we know with rentals charge the entire stay up front. BTW, we did charge the 11% state bed tax.

Not all of Florida is as nice as the SW area in winter. We have blue sky and 70-80 degrees most of the time, which is great for bicycles. Rains rarely last more than an hour or two, then the sky clears. The panhandle and north atlantic coast have much cooler weather. As a result, your rentals will be less expensive there. In our area, it is hard to find anything under $2,000-$2,500 a month for winters.
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Old 08-08-2016, 06:16 AM   #24
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I am becoming less infatuated with the Keys after hearing this. Maybe the redneck Riviera would be better.
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Originally Posted by brucethebroker View Post
The panhandle and north atlantic coast have much cooler weather. As a result, your rentals will be less expensive there. In our area, it is hard to find anything under $2,000-$2,500 a month for winters.
Come on down to Orange Beach, AL. We get lot's of snowbirds during the winter, but I imagine there are more rentals available with better rates as compared to S FL. But as stated, the trade off is cooler temps. There are plenty of nice days in the 70's, but you can have some in the 45-50 range. I enjoy going to my condo during the winter.

Another thought is Sandestin, FL about an hour east of me. My old employer had annual meetings there at the resort. Great golf and fishing. Awesome resort.

Destin Vacation Rentals, Condo
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Old 08-08-2016, 07:10 AM   #25
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Actually 40s and 50s sounds lovely. It has been 80 here in Wisconsin this week and it is still too hot for us. Sunny and 50 is my ideal day.
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Old 08-08-2016, 07:18 AM   #26
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Actually 40s and 50s sounds lovely. It has been 80 here in Wisconsin this week and it is still too hot for us. Sunny and 50 is my ideal day.
You would like it here then. I see more Wisconsin, Michigan, Minnesota, Indiana, Iowa, etc... than AL and MS car tags during the winter.
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Old 08-08-2016, 08:47 AM   #27
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Actually 40s and 50s sounds lovely. It has been 80 here in Wisconsin this week and it is still too hot for us. Sunny and 50 is my ideal day.

We've been in the 80s here, too, but only after about 11PM...
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Old 08-08-2016, 09:47 AM   #28
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We have used Homeaway many times to rent homes for 1-2 weeks in vacation areas. I tend to only consider properties with multiple reviews from earlier renters.


Spent a lot of time with grandparents at their canal home in Tavernier (Key Largo), but hard to find a bad spot in the Keys.


I agree with an earlier post to inquire about any RV restrictions if that will be making the trip with you. Most of my rentals have been in planned communities, that would exclude or really limit the number of days that a RV could park at the house/condo.
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Old 08-08-2016, 11:49 AM   #29
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Actually 40s and 50s sounds lovely. It has been 80 here in Wisconsin this week and it is still too hot for us. Sunny and 50 is my ideal day.
I know a few people who winter in Myrtle Beach. Condo rentals for Dec - Mar are very reasonable, lots of golf available, generally "sweater weather" or better absent an occasional cold spell.

We decided that we were willing to spend more to end up in shorts weather so we ended up in Florida, but if money had been tight then I think we would have considered Myrtle Beach.

Another friend was considering buying there, using his place during their off-season as a winter get-a-way and then renting it during their high season... he was hoping that his winter get-a-way would be low/no cost. I haven't seen him lately so I'm not sure how things worked out for him.
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Old 08-08-2016, 04:19 PM   #30
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I am becoming less infatuated with the Keys after hearing this. Maybe the redneck Riviera would be better.
Ok, now you're speaking my language, lol. I always thought I'd want to spend my winters on the coast or keys of Florida, but in the last few years I've spent some time around Sebring Florida, lots of beautiful sand bottom lakes with plenty of reasonable winter rentals. My favorite is Lake June, very cool bar and grill " Jaxsons " where all the snowbirds and locals mingle. I've come to love the particular area and bar, lol. Good luck with wherever you go.
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Old 08-08-2016, 05:04 PM   #31
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We purchased a place in Ft. Myers, FL ..... It is a 55+ RV Park that you own the land. There are over 680 Lots, some RVs, mostly Park Model Trailers..... You own your lot ..... There are a few people that rent their empty lots out, this way you can bring your RV...... I have heard the rent is $900 to $1100 for the empty lots...... Several rent their Park Model Homes, from $1500 to $2200 per month Jan, Feb, March, April...... The Key West Express runs from Ft Myers to Key West so it is a cheap way to get there, versus driving ..... Cape Coral is another place to look for a home to rent on a canal ....
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Old 08-08-2016, 05:12 PM   #32
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Honestly, if it was me I'd just sell the house up north, buy a house in Florida with air conditioning and not too far from the water, and live there all year 'round. Sounds easier and more fun to me. Why snowbirds like uprooting themselves twice a year when they could be relaxing and having fun instead, is one of life's great mysteries.
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Old 08-08-2016, 05:21 PM   #33
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....Why snowbirds like uprooting themselves twice a year when they could be relaxing and having fun instead, is one of life's great mysteries.
That's easy... variety is the spice of life.... you get to relax and have fun in two different places and spend time outdoors rather than cooped up under air to avoid the stifling heat and humidity of the summer in the South. In the late spring/summer/early fall I have a beautiful view of the water 30' from my front door and numerous family and friends nearby and in the winter I have a nice view of the golf course and many friends nearby (and some family a short drive away).

Many actually enjoy the transition (uprooting). You're automatically forced to clean out the fridge and freezer twice a year.
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Old 08-08-2016, 05:35 PM   #34
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That's easy... variety is the spice of life.... you get to relax and have fun in two different places and spend time outdoors rather than cooped up under air to avoid the stifling heat and humidity of the summer in the South. In the late spring/summer/early fall I have a beautiful view of the water 30' from my front door and numerous family and friends nearby and in the winter I have a nice view of the golf course and many friends nearby (and some family a short drive away).

Many actually enjoy the transition (uprooting). You're automatically forced to clean out the fridge and freezer twice a year.
Yes here in Central MN I totally get the long term snow birding. What I'm finding less appealing every year are the vacations of one to two weeks, not enough time to really relax and a lot pricier per day. On a day where Delta goes down for 5 hours, my first thought is "Thank goodness I'm not flying today !"
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