Best Places to Rent in Florida during Winter

Here are the Best Places to “Snowbird” in Florida During the Winter and Enjoy the Warm Weather.

It’s easier to choose a great place to rent in Florida during the winter, than it is to decide where to move to live full-time. Why?

  • Because you won’t have to worry about hurricanes because the hurricane season ends November 30th. So you can snowbird in Florida’s hurricane evacuation areas near the coast without worry.
  • You “usually” don’t have to worry about avoiding flood zones along the beaches because it rains far less during the winter. Since you’re renting, you’re not obligated to carry a costly additional flood insurance policy to protect where you’ll be staying.
  • If any freak natural disaster does occur, you can just leave and go home. If the place was your full-time home, well…
  • When you book a seasonal rental for the winter (or just a month), you just pack your toothbrush and swimsuit and go!
  • So just choose a best place to rent in Florida during the winter that suits you, go, and leave your cares behind.

Choose a town that’s best for you, based on your interests…

The best places for winter rentals in Florida for golf enthusiasts

Naples in Southwest Florida

Naples is located in deep Southwest Florida and has more golf courses than just about anywhere in the US, especially for such a “small” town. It has a unique historic area right near the beach.

While homes and condos here are among the priciest in the state, winter rental “bargains” can occasionally be found.

The population here swells by about 300% during the winter because many home are owned by people who are only in town during the winter months..

Things to do in Naples Florida from Visit Florida

Other great places to spend winter in Florida if you love to golf

  • Bonita Springs- This town is just north of Naples and is a little less expensive.
  • Punta Gorda- You’ll find a small historic downtown here on the water and plenty of courses. It’s about an hour north of Naples and also less expensive overall.


The Best Places for Winter Rentals in Florida for Beach Lovers.

Siesta Key Beach Florida

Siesta Key has a beach rated as the best in the world, has a great little tropical village and is just minutes from upscale dining and shopping in Sarasota.

Things to do while in Siesta Key Florida from tripadvisor

Other ideal places to snowbird in Florida for the beach are…

  • Apalachicola- Located on Florida’s Panhandle coast. There’s still a little bit of old-time Florida in the area.
  • Bonita Springs- (also on the golf list above++) In Southwest Florida not far from Marco Island, Naples and the Everglades.
  • Dunedin- Beaches and a walkable downtown, a great place to meet people (single?)

florida move guide book cover and discription

Best Places to Spend the Winter in Florida for Those Who Love to Ride Bikes

Fernandina Beach, Florida

Fernandina Beach- Amelia Island biking, historic beach town. Close to the Georgia border, so closer but also a little cooler than south Florida during the winter months.

Has beaches and also a fantastic historical downtown that is one of the most walkable places in the USA. You can’t get a DUI if you’re walking, so enjoy yourself.

Just before writing this I found a fully furnished and equipped townhouse here, available for less than $2000 a month and just a short walk from the beach.

There are cheaper places than that too. Just bring your toothbrush, beach towel and cell phone so every time it snows in your home state, you can call the chumps back home and tell them how nice the weather was at the beach.

Watch the Fernandina Beach Florida Video

Things to do while in Fernandina Beach Florida from tripadvisor

Other places to find a winter home for your your bike…

  • Venice- Access to beaches, historic downtown and many miles of bike trails, many that go to the beach!
  • The Villages- This places has been described as “Disney” for the 55+ crowd.


The best places for winter rentals to just park the car at “home” and walk almost everywhere in a safe environment.

Dunedin Florida (also on our beach lovers and other lists)

Things to do while in Dunedin Florida from tripadvisor

Other Places to consider…

  • Fernandina Beach- It’s featured in another section in this article. Beach, bike, walk, historic downtown. Wow.
  • The Villages- Leave the car parked and walk, or ride your golf cart anywhere in this population 100,000+ retirement community “city”


The Best Places for Winter Rental in Florida if You Want a 55+ Active Adult Community.

The Villages Florida Near Ocala

After a quick online search, I found a fully furnished 3 bedroom 2 bath home with a garage for only $1200 a month in The Villages Florida. Guess what? There’s even a golf cart in the garage that’s included that you can use to travel just about anywhere you wish to go in this amazing “Disney for Adults” retirement community. Sure, almost every retirement community in Florida has a clubhouse and pool, but this place is a self contained city complete with more shops, restaurants and bars than you’ll likely visit.

If you want to guarantee you’ll enjoy warm weather, sunshine and fun this winter, this is the can’t miss choice. Sorry, this place isn’t for amateurs, you must be 55 or older. Make sure to bring a cell phone to send pics back home on particularly cold dreary days there, of you in your shorts, soaking up the sun.


The best places for winter rentals for boating and fishing enthusiasts.

Punta Gorda Florida (also on our golf and other lists)

Punta Gorda is where the river meets the Gulf of Mexico, so it offers a wide variety of boating and fishing adventure. Has a nice little historic village, waterfont park with tennis courts and a large covered wharf “Fisherman’s Village” filled with shops and restaurants. Many Events and festivals are held here too.

Things to do while in Dunedin Florida from tripadvisor

Florida has no shortage of places to enjoy fishing and boating while snowbirding. Here are some of the other best places…

  • Destin- The Florida Panhandle’s fishing, boating and beach paradise.
  • Cypress Gardens Area (freshwater)- Less expensive, less crowded and laid back even for Florida.


Best Places to Spend Winter in Florida Near the Theme Parks in Orlando

If all of Orlando’s theme parks, shopping and dinning options are what you like most about Florida, Winter Park may be your perfect place to snowbird this winter. I mean, it even has winter in it’s name. Renting a place in Winter Park means you can visit the madness of Orlando whenever you wish, but come home to a great town where you can enjoy a more relaxing and peaceful setting.

Winter Park has very a walkable part of town filled with places to eat, drink and shop, so you can enjoy the warm weather and have fun without even going to the city of Disney. I found a number of fully furnished and equipped homes and apartments just a block or two from Park Avenue (the town’s main entertainment area) for less than $2000.00 per month with all utilities included. Not a high price to pay to make the shivering folks back home jealous this winter.
Ron Stack “That Best Places Guy”

  • Want to be certain if moving to Florida is right for you or your family? You’ll know after reading the Florida Move Guide.
  • Is there a better state to relocate to or a better retirement lifestyle for you than moving to Florida? You’ll know after reading How to Retire Happier.

28 thoughts on “Best Places to Rent in Florida during Winter”

  1. We are two coupkes looking to rent for jan feb march 2018 in central florida. We are canadian so with the miney exchange we r looking fir One bed room. One bathroom of course we need two units as we are two couples We are looking to pay from 800 to 1000
    Many thanks
    Carole r

    • Hello Carole,
      Seasonal rentals in Florida are fully furnished and equipped homes, condos and apartments that are usually set up specifically for snowbirds (people who generally rent by the month for 1-3 months during the winter to escape colder northern weather). You only have to bring your toothbrush and swimsuits. However, since Florida is still in a boom, it won’t be easy to find two 1BR/1BA seasonal rentals for under $1000 or under a month each, especially in locations where snowbirds desire to stay. However, searching this early (February 2017) for a place for winter 2018/2018 will give you the best possible shot at locating a nice but affordable place. The lowest priced nice places get rented first of course.

      Most 1BR/1Bath places built in Florida were intended to rent as unfurnished rentals in apartment complexes with a yearly lease. 2BR/2BA apartments, condos and homes are far more common in Florida. It would probably be much easier to locate a 2BR/2BA seasonal rental for $2000 or less that you can share. As the book nHow to Retire Happier says about snowbirding, if you’re doing it right, you’ll be spending most of your waking hours outside of your snowbird winter home in Florida. Good luck Carole.

      Ron Stack

      • Want to be certain if moving to Florida is right for you or your family? You’ll know after reading the Florida Move Guide.
      • Is there a better state to relocate to or a better retirement lifestyle for you than moving to Florida? You’ll know after reading How to Retire Happier.
    • My husband aND I are are in the same situation, we need to be with like minded adults. Figuring it all out.

  2. Hi. How did u make out for finding a place this winter. We r looking fir next year. Just wondering
    Many thanks
    Carole r

  3. I am considering renting our Fl 3 bedroom house for the first time.
    It has a screened lanai with beautiful pool and situated right on the 12th hole of a golf course. The HO association requires 3 month minimum for rental approval.
    Could rent Jan, Feb, Mar of 2018 for $7500.00 total.
    It’s 2 hrs from Orlando, 3 miles to ocean.

  4. Needing help on where in Florida to go for a couple of weeks in January. By the water for sure. Everyone seems to have different options. Wanting something affordable and maybe want to come back to every year. We do not need fancy

    • Hello Sue,
      The Florida Move Guide and How to Retire Happier both talk about winter being the best time (the ONLY time?) to be in Florida. The 6 month hurricane season is over. The heat and humidity that can be unbearable for up to 9 months every year or longer in Florida, is gone. There’s a lower chance of ran every day. There are less bugs, etc. I will be writing a new post on the best places to snowbird in the winter, but the truth is, any of the many towns on our best places lists will work. Many people are more than happy just enjoying the great winter weather in Florida. You don’t necessarily need to be right at the beach or near the gate of the theme parks. Besides, that’s where most of the winter crowds are and it will cost more. You can go to the beach or a theme park for a day from just about anywhere in Florida.

      Some Florida snowbird tips:

      1) Forget “a few weeks”. The smartest way to spend winter in Florida is to find fully furnished seasonal rental homes or condos that are rented by the month. They cost less than renting the similar places by the day or week, and your “neighbors” won’t likely be a group of rowdy teens on a week long vacation binge.

      2) As the book’s above say, if you’re doing it right, you’ll be spending most of your time outside of the place you sleep, so large and fancy isn’t required. If anything, look for a lanai (a covered patio that’s screened in and pocketing sliding glass doors that open up to it) because you can open the door up and let that warm fresh air in and enjoy dining out there or enjoying a drink. It will extend your “living” space.

      3) Book early. The best places that are cheap are rented first of course. And yes, when you find a suitable place you can afford, book it for the following year before you leave. Many people stay at the same place year after year because that works for the landlord too who doesn’t have to look for new renter every year and therefore may hold off on price increases to keep a good “snowbird”.

      4) Stick to a town that is on any of our lists to avoid renting where crime rates are high. It would be hard to enjoy great weather if you’re stressed out because you have to worry about your personal safety.

      5) Being a snowbird is different than being a tourist. Being a tourist is expensive, so many feel they have to try to cram in tons of stuff to do in just the few days they’ll be there. That in itself can be stressful. So, there’s a long line to get into the restaurant for dinner? Tourist get stressed out because time is short. Full-time Florida residents get mad because it’s winter and they can finally get out of the house without sweating to death, but because of the snowbirds they have to wait in long lines. Snowbirds? They just relax and enjoy a drink, conversation and the weather while waiting. Ah, to be a snowbird in Florida during the winter…

      Good luck Sue and enjoy!
      Ron Stack

      • Want to be certain if moving to Florida is right for you or your family? You’ll know after reading the Florida Move Guide.
      • Is there a better state to relocate to or a better retirement lifestyle for you than moving to Florida? You’ll know after reading How to Retire Happier.
  5. I am interested in renting for January,February and March of 2019, either Venice or the villages near Ocala. Please contact me. Thank you.

    • Hello Renee,
      The best way to book a place in Florida for the winter is to 1) decide where you want to stay and then 2) search “name of town” seasonal rentals. For instance, for Venice search “Venice FL seasonal rentals”. Then take a look at the rentals and prices on the websites the search returns and see if they will work for you. Booking now for next year, a full year in advance, will help you secure a better place, location and price. Good luck Renee.
      Ron Stack

      • Want to be certain if moving to Florida is right for you or your family? You’ll know after reading the Florida Move Guide.
      • Is there a better state to relocate to or a better retirement lifestyle for you than moving to Florida? You’ll know after reading How to Retire Happier.
    • Dear Ron , [ tried to rent an apartment and searched every where in Orlando Florida during 2017 and when I started calling there answer was only if I agreed to rent for a 12 month lease. That was very dissappointing ! Well my ticket was already bought for January 11 , 2018 thru 27th and I enjoyed stayong in motel 6 . So I have decided to rent for 3 months at In-town suites and really I would be satisfied but but now I am back looking something else . Paying that much a month in a motel maybe a condo could be my answer ? For MARCH APRIL , MAY IN 2020 . cuse I have my home in Michigan . Would the utilities be included in the rent ? I do not drive and I want TO STAY IN oRLANDO fLORIDA AND USE PUBLIC TRANSPORTATION My E-mail is ***************** and only can I read them when going to library once a week . Everything I need is there in a motel Thank you Donna

      • Hello Donna,
        The Florida Move Guide and How to Retire Happier thoroughly explain what “Seasonal Rentals” in the state of Florida are. Many real estate broker offices only handle sales, not rentals. Even less handle seasonal rentals. But there are tons of seasonal rentals everywhere in Florida worth staying, and lots of offices that rent them. For instance, for seasonal rentals in Orlando Florida, search “seasonal rentals Orlando Florida property management”. Most seasonal rentals rent only by the month and at a reasonable rate. Many condos and homes seasonal rentals are in areas that only allow rentals of 30 days or longer. This maintains the “neighboorhood” residential feel as these tennants are usually wealty, retired or business people who need a place for a month or longer.

        However, in a place like Orlando with so many people just coming in for a week, you’ll want to avoid paying a high weekly rate x 4 weeks. If you rent for months in a place that offers daily (hotel) or weekly rates, as opposed to “by the month” only, sooner or later you’ll be next door to tourist that you’ll have to call the cops on because of late night drunken parties, or worse. We don’t recommend Orlando because of high crime rates, but good luck Donna.
        Ron Stack

        • Want to be certain if moving to Florida is right for you or your family? You’ll know after reading the Florida Move Guide.
        • Is there a better state to relocate to or a better retirement lifestyle for you than moving to Florida? You’ll know after reading How to Retire Happier.
  6. ngngI’m a retired leo, spend My winter”s in florida, have a two bedroom fifth wheel, located in new port richey, poss. roommate?, in exchange for very little help around here. I’m still recovering from radiation treatment for lung cancer. clear now and doing good.

  7. Hello, we are snowbirds and staying in Kissimmee Florida. Last year we stayed at the same motel for most of our stay, two months. This year we are at the same motel but this time the new management told us that we can only stay at one motel no more than 28 days a year. I have not been able to find any information stating that we can stay longer because we are American snowbirds. Do you know if this is true? Thank you for any help you may be able to provide us. Merry Christmas and Happy New Year’s

    • Hello Paula,
      Why stay somewhere you aren’t welcome? Motels are for tourist staying in Florida for a week or so. Almost all snowbirds in Florida during the winter (staying for a month or longer) stay in fully furnished “seasonal rentals”. These are fully furnished and equipped homes, condos and even manufactured homes that can be rented for the same cost or often less than staying in a cramped motel/hotel room. If this motel doesn’t want your business, find a better and possibly less expensive place to stay and if you like it, reserve it for next winter BEFORE you leave, like most annual snowbirds do.

      Also, Kissimmee’s is not on any of our best places lists because violent crime is twice the national average. Right next door, St Cloud’s violent crime rate was already lower than the national average and decreased further year over year according the the latest FBI reporting. Don’t let those owners/managers stress you out, find another place (better town and accommodations) and enjoy the best time to be in Florida, the winter! Good luck Paula.
      Ron Stack

      • Want to be certain if moving to Florida is right for you or your family? You’ll know after reading the Florida Move Guide.
      • Is there a better state to relocate to or a better retirement lifestyle for you than moving to Florida? You’ll know after reading How to Retire Happier.
  8. I am looking for a 2 bedroom apartment furnished to stay from 12/27/18 to 3/27/19 or so this is a furnished stay this could be a condo as well this could be an every winter stayI need all the info of places in the area

  9. I haven’t seen video’s on any other site about the city where people might want to go for the winter. This helps tremendously in making a decision.

  10. Looking for a two bedroom rental for brother and sister in their 70’s for December 2019 until the end of April 2020 for $1000.00 or less per month.Have two small dogs.Looking for a place from southern to central Florida.

  11. Hi,
    I’m looking for the winter of 2022 and I am shocked at the rental prices. I wanted to spend no more than $3,000 per month. My husband will be flying back and forth so I need to feel very safe. I wanted gated community with activities.

    Any suggestions or should I start looking at other states?



    • As Florida real estate prices (values) inflate toward the sky, a landlords taxes, insurance and other expenses also increase. More demand (including from highly paid remote workers fleeing covid and locked-down restaurants, bars, etc.) for rentals than available supply equals higher rental prices. If you’re looking for warmer weather during the cold northern winter weather, there are other places (both states and countries) with lower winter rental prices. Many also currently, until they’re discovered, offer a more relaxed less congested experience.
      Ron Stack “That Best Places Guy” of Zeus Press Inc

      • Want to be certain if moving to Florida is right for you or your family? You’ll know after reading the Florida Move Guide. Avoid expensive mistakes.

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