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Rent a wintertime vacation home in these 5 US destinations

Sept. 07, 2020
13 min read
Beach scene, Clearwater, Florida
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It's become clear that the novel coronavirus is going to be with us for longer than we all had expected. With many schools in remote mode and companies telling employees they won't return to the office until at least January 2021, many families are researching the possibility of a longer-term getaway this winter. Call it a change of scenery, an escape from cold weather that will keep people indoors or the opportunity to test drive a new home base, many people are looking into home-away-from-home hotel vacation packages that allow them to work from the road or vacation home rentals.

If you're searching for a vacation home rental for this winter, you're probably seeing a few trends. Availability -- especially in traditionally popular destinations like Miami and Fort Myers -- is already getting tight. Rules are also changing and you may find a lot more homes with a minimum rental period of 30 days. And, you may pay top dollar for the nicest homes at the best addresses -- be they in Florida, California, Colorado or Vermont.

Here are five places to look for extended-stay vacation home rentals this winter.

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Florida's Gulf Coast

Sanibel Island Florida
Sanibel Island at sunset. (Photo by Maridav/

While all four corners of Florida have something to offer visitors, the Gulf Coast is particularly special during the winter months. Temperatures are warm but not blazing hot. You can often see manatees and all manner of birds in the state's rivers, estuaries and beachfront. And, since it's high season with visitors usually calling from around the globe, attractions and restaurants are expected to be open in full force.

Related: Airbnb, Vrbo and More -- Comparing popular vacation home-booking sites

The Gulf Coast covers a lot of ground so you'll need to narrow down your options before searching for the perfect vacation home. If you'd prefer to be near a city with museums and other cultural attractions, your best bet is the Suncoast, where St. Petersburg, Tampa and Clearwater are all located. If you're flying instead of driving, it's a snap with Tampa International Airport (TPA), St. Pete-Clearwater International Airport (PIE) and Sarasota Bradenton International Airport (SRQ) all in the area. Also nearby are a variety of outdoor venues, such as the renown Caladesi Island State Park, Fort De Soto Park and Tarpon Springs.

A bit farther south is the Cultural Coast, which includes Sarasota and Port Charlotte plus destinations such as Siesta Key, Anna Maria Island, Lido Key, Venice, Manasota Key and Boca Grande. Myakka River State Park and Forest, Oscar Scherer State Park and Warm Mineral Springs Park are the outdoor draws here in addition to the barrier islands and mainland coast.

Continue south and you'll arrive at Lee Island Coast -- what many consider to be the crown jewel of Florida's Gulf Coast. Fly into Southwest Florida International Aiport (RSW) for Fort Myers, Sanibel and Captiva islands, Bonita Springs, Naples and Marco Island. While vacation home rentals have always had a minimum rental period of 30 days on Sanibel, you can find shorter terms in other nearby communities.

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Related: How to find the perfect beach house rental

Rental homes in the Fort Myers area start around $2,500 a month and most have private pools. Prices go up for properties close to the beach or with a dock. Luxury homes or those on Sanibel Island or Marco Island can set you back $5,000 to $8,000 a month, depending on location and amenities.

Here are a few examples of the type of homes you'll find on the Gulf Coast.

This high-end home with a private pool, hot tub and dock goes for just shy of $10,000 for January.

View On AirbnbInviting waterfront home w/ heated pool, hot tub & short walk to beach

Just a short walk to Bowman's Beach on Sanibel, this three-bedroom, three-bath home accommodates seven people and goes for $6,440 a month in January.

View On AirbnbBowman's Beach Home!

In Siesta Key, you can find rental homes like this one -- within walking distance of the beach -- that also has a private dock. This home is available in January for $5,250 for the month.

View On Airbnb3BR Waterfront Siesta Key Home-Dock-Walk toBeach

Here are some more resources that will help pick the perfect Florida getaway:

The Berkshires, Massachusetts

sleigh ride Stockbridge, Massachusetts Berkshires
You can enjoy a sleigh ride in Stockbridge, Massachusetts. (Photo by James Kirkikis/

Not everyone is looking to get away from cold weather. If that describes you, The Berkshires in Western Massachusetts may be a good fit. It's magical there when snow blankets the region and many of the rentals have a backcountry, log cabin rustic feel. The towns to target in your rental home search include Lee, Lenox, Stockbridge, Great Barrington (which is home to an excellent brewery, by the way), Hancock, Lanesborough, Tyringham, North Adams, Pittsfield and Plainfield.

The area is comprised of a series of small towns surrounded by state forests like Beartown, Becket, Middlefield, East Mountain and October Mountain. You will not feel the pull of the big city here. From Stockbridge, it's a two-hour drive to Boston and three hours to New York City.

Related: 13 mistakes to avoid on your next vacation home rental

In the winter, you can ski, snowboard and snowmobile throughout The Berkshires with Jiminy Peak, Notchview, Butternut, Bousquet and the Berkshire East Ski Area being popular with those that want to hit the slopes. Cross-country skiing is also available at Canterberry and Maple Corner farms.

Just know going into your rental that many attractions (historic homes, museums, gardens and performing arts venues) close through the winter season as do some restaurants. But if your goal is to enjoy your vacation home, the cold weather and the snow, The Berkshires are a good option.

Here's a taste of the rental options in The Berkshires.

Have you ever wished you lived in a Victorian manor? You can at this rental home in Lee for $6,370 in January.

View On AirbnbVictorian Manor Berkshires

In West Stockbridge, you'll find this charming lakefront home that goes for just under $3,000 in January.

View On AirbnbWest Stockbridge MA gem, in town and facing lake

In the Green River Valley in Hillsdale, this spacious home runs $5,400 in January. Just watch the roads in the winter, this is off the beaten path.

View On AirbnbWest Stockbridge MA gem, in town and facing lake

If you just want to visit The Berkshires for a short stay, check out Hyatt's brand-new Miraval Berkshires.

Phoenix and nearby towns

Phoenix Arizona hike
Spend the winter in Phoenix and you can hike every day. (Photo by Globe Guide Media Inc./

With beautiful weather throughout the winter, Phoenix or any of the nearby cities of Glendale, Scottsdale, Tempe, Mesa, Gilbert or Chandler may be the perfect spot for a home rental. Like other areas we've recommended, there are plenty of nature reserves in this area too. Look for McDowell Mountain Regional Park, Cave Buttes Recreation Area, Phoenix Sonoran Preserve, Phoenix Mountains Preserve and South Mountain Park and Preserve.

Related: How to maximize earnings on vacation home rentals

Without the searing temperatures this area sees in the summertime, you'll be able to spend plenty of time outdoors -- hiking, biking and enjoying your home's private pool. And, the location can't be beaten if you also want to do some day trip sightseeing. You can visit the Grand Canyon (season and weather permitting), Sedona, Tucson, Flagstaff and the Petrified Forest National Park in northeastern Arizona.

There are a range of options in the Phoenix area for rent this winter.

In Phoenix near Old Town Scottsdale, this home has an incredible backyard that includes a pool (with slide!), bar and multiple seating areas. It goes for $7,735 a month in January.

View On AirbnbGorgeous Getaway- Near Old Town Scottsdale

This home in Glendale is a keeper. It's got a dedicated game room with an air hockey table and foosball. With four bedrooms and 2.5 baths, it accommodates up to eight guests for $4,389 a month in January.

View On AirbnbGlendale getaway

And, if you're just looking for a warm location and a private home, check out what's available in Mesa. There are some incredibly affordable options like this home that goes for just under $2,000 for January.

View On AirbnbSingle story, Open Floor plan, East Mesa, AZ home.

San Diego and its environs

Mission Beach in San Diego. (Photo by Art Wager/Getty Images)
Mission Beach in San Diego. (Photo by Art Wager/Getty Images)

Southern California's San Diego is a hot spot for tourists and it's not so easy to find bargains here -- especially for home rentals. But, there are some solid options in the city as well as nearby in Chula Vista, La Jolla, Del Mar, Solana Beach, Carlsbad and Encinitas.

Related: How to use points to book vacation home rentals

Families adore this area because there's a lot to do. Nearly everyone takes a harbor cruise, visits nearby La Jolla for kayaking, hits up the San Diego Zoo, enjoys Old Town via a hop-on hop-off trolley, visits Legoland and checks out Balboa Park. Read more about San Diego's attractions.

Pick this home in Carlsbad on the Pacific Coast Highway and you'll have beach access directly across the street. It's part of Airbnb's "Plus" collection, which means there are more luxuries -- like Westin beds -- than you'll find at traditional listings. This one goes for $4,857 for January.

View On AirbnbResort-Style Beach House on Pacific Coast Highway 101

The view from this home in Oceanside will make you swoon. You are right on the water with incredible ocean views. At just about $10k for January, this beachfront home is worth every penny.

View On AirbnbBeach house, private sand, 2bd+ multipurpose suite

This luxury home in the Mission Hills neighborhood has stunning 270-degree views of San Diego and the bay. Expect to pay $8,261 per month in January.

View On Airbnb♥ Luxury Hilltop Retreat in the City - No Expense Spared! ♥

Roll the dice in Las Vegas

You don't even need to like to gamble to consider a wintertime vacation home rental in Las Vegas or nearby Paradise or Henderson. Of course, this being a desert, the evenings do get chilly here in the winter but all the better to enjoy that fire pit on the patio of your rental home. And, daytime temperatures from January through March range from an average of 59 to 72 degrees.

Related: Maximizing points and miles on vacation rentals with Airbnb and Vrbo

There are plenty of outdoor adventures to be had here in the winter as you visit Sloan Canyon National Conservation Area or Red Rock Canyon National Conservation Area. And, you're within driving distance of the Hoover Dam, Antelope Canyon, the Grand Canyon and Zion and Bryce Canyon national parks. You can also easily drive to Los Angeles or Palm Springs from Vegas.

There are home rentals at all price points in Las Vegas.

If you're seeking an estate instead of a mere home, look no further than this four-bedroom, 3.5 bath property that features an incredible pool, full-court basketball court and views of the Strip. It goes for $10,159 a month during January.

View On AirbnbLicensed Luxury estate with Amazing Strip Views!

Or, splurge on this beauty with an incredible pool deck, outdoor sitting areas, fireplaces in multiple rooms and several arcade-style games. It's available for January for $12,348 and accommodates up to eight guests in four bedrooms and three baths.

View On AirbnbSuper Private Vegas Resort! Close to the Strip!9:)

Out in Henderson, check out this home with a private pool, outdoor dining area and very private yard. The three-bedroom, 2.5-bath home goest for just about $5,000 for January.

View On AirbnbLas Vegas-Hendreson Home with Pool and waterfall.

Bottom line

This winter, you may want to be inspired by new surroundings -- at least for a few weeks or months. If you know you're working from home for the rest of the year, and that the kids will be doing remote school, why not search for the perfect vacation home to enjoy as a reset before the New Year? Book now before all the prime properties are picked over.

Featured image by Getty Images/Image Source