Winter can bring unique challenges and opportunities for vacation rental property managers and investors, whether you’re in the sunny climate of Orlando, Florida, or possibly somewhere wetter and colder like Seattle, Washington. If you’re looking to buy a property to turn it into a vacation rental, this comprehensive winter season VR maintenance checklist compiles insights and recommendations from seasoned professionals in the industry.
From yearly maintenance routines and safety inspections to adapting property management approaches and providing guest-centric amenities, these tips aim to ensure a delightful and hassle-free experience for guests during the winter season. Whether you’re preparing for snowstorms or optimizing heating systems, this Redfin article covers it all, emphasizing the importance of proactive measures, clear communication, and a guest-first mindset for achieving VR success in the competitive vacation rental market.
1. Have a maintenance checklist for each season
“As one of Seattle’s most successful short-term rental managers, we prepare our homes for winter and the holidays to ensure a great guest experience,” says Eva and Sid, co-founders of NICASA. “On the backend, we conduct annual maintenance, including gutter cleaning, covering outside hose bibs to prevent pipes from freezing, cleaning heater vents, and checking their functionality while preparing backups in case of any failures. We also place ice melt and shovels in homes to be ready for unexpected snowstorms — we recommend purchasing them in advance as they sell out quickly when storms occur.”
Courtesy of NICASA
2. Get your guests tickets to local activities and events
At HomeSlice Stays, “We understand that the winter and holiday season is a special time for guests and their loved ones. We want to ensure that every moment of their stay is filled with joy, comfort, and relaxation. Our team is dedicated to providing the highest level of service and support throughout their visit. To add an extra touch of holiday cheer, we offer Christmas hot chocolate and champagne baskets as a warm welcome gesture. In addition, we offer tickets to local activities such as Enchant, Scottsdazzle, or maps for the best local holiday lights. It’s our little way of spreading joy and making your vacation feel special.”
Courtesy of HomeSlice Stays
3. Complete a safety inspection
“As a traveler and vacation home manager, we take safety extremely seriously,” says Caleb Hannon, COO of StayLakeNorman. “That’s why we use the winter time to do a robust safety inspection of all of our properties and luxury homes, from checking outdoor lighting, to testing smoke detectors, and all the way to cleaning out dryer vent systems. We conduct several preventive maintenance checks throughout the year, with the most extensive one just before winter to ensure our properties provide the best possible stay for our guests. Continuous preventative maintenance and safety inspections are key to ensuring vacation rental properties are ready for anything or anyone.”
Courtesy of StayLakeNorman
4. Prepare for cold, frigid weather
“Here in Northern New England, we are lucky to have a slowdown in rentals between the foliage season and the busy holiday seasons, which allows us to fully prepare for winter,” mentions Bretton Woods Vacations. “Our climate is harsh in New Hampshire. I have personally seen temperatures as low as -35F. While rare, those temperatures bring on a suite of potential problems, from frozen pipes to dead car batteries. For those reasons, we change our cleaning protocols to ensure that thermostats are set no lower than 60F, and that sink base cabinet doors are left open to allow better air circulation. Our maintenance team also has jumper cables so that they can promptly intervene to help a guest in case of a vehicle that won’t start in the cold weather.”
Courtesy of Bretton Woods Vacations
5. Provide clear communication, instructions, and regular updates
“In my extensive experience with vacation rental management, specializing in Airbnb and VRBO, I’ve learned that guest reviews and safety heavily influence success,” suggests 5 Star STR.“Clear communication is another key aspect. In my short-term rental management approach, I make it a point to ensure our guests receive a digital guest book providing clear operating instructions on heating equipment and readily available emergency contact information. Our secret to 5-star reviews is our proactive communication and property DNA. We respond to guests within five minutes, 24/7, and deal head-on with any situation.”
Courtesy of 5 Star STR
6. New filters and air purifiers
“Taking proactive measures to prevent the spread of germs and allergens ensures a happy and healthy holiday for everyone – including your next guests,” recommends Justin Ford, Director of STR Safety at Breezeway. “Install new filters for all forced-air heating systems. These filters will capture airborne particles, including dust, pollen, and even viruses, preventing them from circulating throughout the property. Hosts should also consider adding air purifiers with filters to common areas. These will silently remove allergens, viruses, and bacteria from the air, creating a healthier and more comfortable environment for guests.”
7. Invest in comfort, technology, and guest feedback
Sophari says, “Our property management approach in Seattle revolves around creating a truly memorable experience for our guests during the winter season. Here’s how we blend these elements to make our vacation rentals special during the winter:
- Temperature control and enhanced monitoring: We prioritize guest comfort by utilizing Nest devices to maintain a warm property during the coldest winter nights. Proactive measures, such as preheating vacant units before arrivals, ensure a cozy and welcoming environment from the moment guests step in.
- Smart Locks and battery monitoring: We guarantee a hassle-free experience with SmartThings technology, connecting with Yale Smart Locks through our property management software. This system monitors smart lock battery levels to prevent lockouts and unauthorized access, ensuring a smooth check-in and restricting access only to valid reservation dates.
- Guest feedback and continuous improvement: To consistently exceed guest expectations, we personally stay in our units annually or invite close friends and family for feedback. Aggregating this input, along with guest reviews, allows us to identify areas for improvement and enhance the overall guest experience.”
8. Be ready when unexpected weather arises
Brigadoon Vacation Rentals suggests that “Sometimes, guests’ plans for hiking, biking, or kayaking can be waylaid by rainstorms or occasional snowfall. Here are some tips to help prepare your vacation rental space for the winter season:
- Soft furnishings: Warm blankets, plush throws, and cushions create a cozy atmosphere.
- Rugs: Decorative rugs add warmth to hard floors.
- Lighting: Battery-operated candles (for safety), fairy lights, or warm-toned lamps create a soft and inviting ambiance.
- Seasonal: Rotate winter-themed decor.
- Curtains: Consider heavy curtains for windows to help trap heat inside.
- Heating: Turn the heat to 55 when vacant, but turn it up before check-in. Leave a few instant logs for the fireplace.
- Winter reading: Create a cozy area with a comfortable chair, task lighting, and a selection of books.
- Movies: The TV room should have plenty of blankets and pillows.
- Games: Keep a collection of family-friendly board games.”
Courtesy of Brigadoon Vacation Rentals
9. Deep clean and get your fireplace ready
iTrip Los Angeles recommends, “Clean your rental from top to bottom, including ceilings, stairwells, baseboards, closets, and all the nooks and crannies. This will help with general upkeep and also help you identify opportunities for improvement. For example, you may notice while cleaning your window sills that they could use another layer of caulking. Or that your outdoor faucets still need to be winterized. You should also replace the batteries in your smoke detectors, inspect your furnace and space heaters, and change HVAC filters. Lastly, clean out the fireplace (including gas fireplaces) and test them out to make sure they’re working properly.”
10. Adapt property management to the winter and holiday season
Phillip Costa, co-founder of Desired Stays recommends, “Adapt your property management approach to the winter and holiday season. Increase the frequency of property inspections, focusing on heating systems to ensure functionality. Adjust cleaning routines to address mud and snow, maintaining a clean and welcoming environment. Enhance guest support with quick responses to inquiries and a detailed guide on winter activities and local holiday events, ensuring a smooth and enjoyable stay.
Schedule maintenance for heating systems to avoid unexpected breakdowns. Provide straightforward instructions for operating heating equipment, thermostats, and other appliances. Ensure a reliable Wi-Fi network and trouble-free smart home devices, offering a seamless and comfortable technological experience for your guests.”
11. Provide entertainment options for both indoor and outdoor
Zach Vavak, owner of Grand Welcome Lake of the Ozarks says, “Fire pits are popular during the winter. Here at the lake, it’s a perfect spot to relax around a warm outdoor fire. We recommend getting comfortable chairs made from water-resistant materials. Indoor entertainment and outdoor experiences and activities at the lake are plentiful. If you opt for a cozy cabin or condo stay, provide indoor board games and TV streaming services. Meal delivery should also be available. If your guests decide to venture out, let your guests know the town offers a variety of options, like ice skating, Christmas light villages, indoor play areas, trampoline parks, indoor pools, and much more.”
Courtesy of Grand Welcome Lake of the Ozarks
12. Small details can go a long way
“Hot tubs, saunas, and Jacuzzis are fantastic for keeping winter guests happy,” recommends Lucas Knowles, owner of Grand Welcome Southern Coastal Maine. “But better winter comfort doesn’t have to come with a hefty price tag. Adding extra blankets and boot warmers provides a cozy touch, while a well-stocked kitchen with wine glasses, a bottle opener, and hot cocoa can really elevate the experience. Proper cookware, mixing bowls, and a can opener are all easily forgotten items that guests will be relieved to find in the home, saving them an emergency trip to the store.”
Courtesy of Grand Welcome Southern Coastal Maine
13. Weather proof your rental, even in warmer climates
Ian Vogt, manager of Grand Welcome Destin & Miramar Beach mentions, “In Florida’s winter season, though lacking snow, essential tasks beckon attention. Key among them is weatherproofing—sealing windows and doors, inspecting the roof and gutters, and engaging professionals for HVAC system checks. Pool owners should adapt cleaning routines for cooler temperatures and activate heating for a delightful experience. Indoors, create a cozy ambiance with plush blankets in each bedroom, stock the kitchen with holiday cooking essentials, and consider adorning the vacation rental with enchanting holiday decorations for an extra touch of magic, consistently charming guests.”
14. Avoid technical difficulties using easy alternatives
Jay Breitlow, owner of Grand Welcome of Greater Orlando says, “We live in Florida so our challenges are unique to guests who stay in our homes but the most common issues we have are really quite simple. The first issue we run into is switching our thermostats from cooling mode into heating mode. It’s super easy when you know your thermostat but guests somehow always seem to have an issue. We highly recommend recording a video and saving to YouTube and then printing off a QR code for them to scan with the basics of how to use the thermostat.”
15. Prepare your water lines
Niyi Olumide, owner of Grand Welcome Houston recommends, “Opening faucets and dripping or draining water lines helps to avoid water getting stuck and freezing inside the pipes. Insulating our pipes with insulating tape or foam – padding sleeves is really important. We apply foam-padding sleeves to the outside of the pipes, which will help keep them warm and the insulating tape will also keep pipes warm, but will keep water out, as well.”
16. Focus on maintenance, cleaning, and energy efficiency during the winter
Owner of Grand Welcome Franklin, Josh Smith mentions, “Here are some notable changes in how we handle maintenance, cleaning, energy efficiency as well as guest support during the winter/holiday season.
- Maintenance: schedule professional HVAC inspections leading into winter as well as into summer (Bi annual visits) to help mitigate any potential system issues.
- Cleaning: If applicable, fireplace/chimney as well as outside gutters and downspouts cleaned.
- Energy efficiency: programmable thermostats for interior HVAC is a huge efficiency saver. During the winter season, we set thermostats to 65F when vacant and 70F prior to guest arrival.
17. In-unit amenities and comfy furniture
“The key considerations for guest satisfaction revolve around comfort, quality, and attention to detail,” recommends Taylor Porter, Owner of Grand Welcome Hilton Head Island. “Comfortable furnishings such as mattresses, plush sofas, and ample cushions contribute to a relaxing and cozy atmosphere. Quality entertainment, kitchenware, and in-unit amenities, like a washer and dryer, add value and convenience to the guest experience.”
18. Create a grand experience outdoors and indoors
Lucas Ha from Sweet Vacation Rental says, “We’re prepping our Orlando and Tampa homes for a cozy winter. Picture fairy lights on palm trees without icy sidewalks. We clear walkways, trim fronds, and swap patio furniture for sturdy pieces with plush throws. Our fireplaces get professionally checked, and we add LED lights for festive cheer.
Indoors, we welcome guests with garlands, beach reads, and board games. The kitchen has spices for cocoa and baking. Bathrooms get spa vibes with fluffy towels and scented soaps. We test everything, from pool heaters to tech, and our guest book has local info. We update guests on weather and provide emergency contacts. Before arrival, our cleaning team works their magic, ensuring a sparkling space. We restock pool floats, sunscreen, and leave a welcome basket with fresh oranges and local honey.”
19. Require guests to also come prepared
“We manage properties in Northern Utah’s Wasatch Back and require our guests to have a 4-wheel or all-wheel drive vehicle to access their ‘home away from home’ during the winter,” says Mountain Luxury Real Estate. “Too often, our guests get stuck or are unable to drive safely from the airport due to intense winter weather. Of course, there are a few guests who visit during a dry spell and complain that they didn’t need 4-wheel or all-wheel drive; however, we prefer those complaints over ones like, ‘I slid off the road. Please refund me.”
Courtesy of Mountain Luxury Real Estate
20. Create a warm welcoming environment
“Our holiday season mantra is all about preemptive cheer and flawless experiences,” shares WISH Short Term Rental. “As winter settles in, our focus is on perfecting every detail for a seamless and cozy guest experience. We prioritize hassle-free access with smart lock systems, align pricing with festive market trends, and conduct comprehensive preventative maintenance, addressing heating systems and insulation. Our goal is to provide a welcoming and warm haven for guests, allowing them to fully enjoy their stay without worrying about anything other than packing in as much holiday fun as possible.”
21. Think gift baskets and coziness
“We’ve found that creating a warm and cozy environment is essential to providing an ideal winter getaway,” mentions Stay & Sea. “Little touches go a long way, we like to leave seasonal treats in our gift baskets for guests to enjoy. Supplying soft throw blankets and plush robes is a great way to help guests relax and feel at home. Many of our rentals offer fireplaces, saunas, and hot tubs. We can’t think of a better way to stay warm and toasty during the chilly winter months.”
Courtesy of Stay & Sea
22. Invest in a heated pool for a year round retreat
“Invest in the year-round luxury appeal by strategically adding pool heaters to your vacation rental properties,” recommends David Soper from 5 Star Stays Vacation Rental Property Management.
“In colder months, offering a heated pool not only fulfills guests’ desires but also enhances your property’s market value. The ability to upcharge for extra electricity usage during cooler stays offsets the cost of pool heater installation, turning it into a lucrative opportunity. Market insights in Myrtle Beach, SC, show that properties with pool heaters experience a 10% increase in rental rates and a 35% boost in occupancy. It’s not just about having a pool; it’s about transforming your investment into a year-round retreat that attracts and rewards guests in all seasons.”
23. Create long term partnerships with local professionals
“A few simple practices can help you navigate the surprises the winter months bring in vacation rentals,” says Jessica from Hudson Valley Short Rental Management. “We like to stay proactive and pivot when we need to. Keeping a team of professionals on speed dial is essential. Check in with your plumber, electrician, and HVAC partners before the cold weather hits, and be sure to choose reliable professionals that answer emergencies and work weekends.”
Courtesy of Hudson Valley Short Rental Management
24. Find a snow removal company that’s available 24/7
“As the winter season approaches in Colorado, one crucial tip for hosts that surprisingly gets overlooked is to have a reliable snow removal solution in place for your vacation rental,” recommends Highline Management. “There is nothing worse than experiencing an unreliable service that doesn’t come out during one of the biggest snowfalls, resulting in leaving your guests snowed in.
Given Colorado’s unpredictable weather, the key to a seamless stay lies in sourcing a reliable snow plow or shovel service in place from October through May. Make sure your service provider comes out to shovel and ice after the first inch of snowfall. We do see a lot of travelers coming from the warmer states that appreciate this precaution ensuring that their family is safe and taken care of during their stays.”
25. Provide back up plans for your guests
“As a professional short-term rental manager, we strive to create a cozy and welcoming environment for guests,” says Karen Hunt, Owner of iTrip Seattle. “We have a local inspector who personally checks each home and turns up the heat before guests arrive. During slick conditions and snowy weather, we send direct messages to our guests with alternative driving routes because Seattle has some steep roads. Our goal is to not only provide great vacation rental accommodations, but also help travelers have a five-star experience each time they visit.”
Courtesy of iTrip Seattle
26. Provide exceptional customer service and frequent check-ins
“We’re in Scottsdale, AZ, so no snow, but plenty of snowbirds looking for some golf and sun,” says GemHaus. “Winter’s our peak season, and that means a lot more guests soaking up the desert vibes. The only hiccup? Our pools can get a bit chilly during the winter. We’re on it, though— helping guests figure out those pool heaters is like our winter sport. At GemHaus, we’re all about more check-ins, extra guest love, and making sure everyone gets a sunny winter getaway they’ll remember.”
27. Have the basic essentials ready for travelers
“One of the significant gestures we extend to all our guests is a welcome basket containing water, snacks, oatmeal, Skittles, and popcorn,” suggests Book It Vacation Rentals. “The Skittles are more of an inside treat for Seattle Seahawk fans. Additionally, we provide an excellent box that equips travelers with all their essential travel needs: a shaver, shaving cream, toothbrush, toothpaste, sewing kit, shoe polish, toothpicks, mini tissues, comb, and sleep spray.”
28. Complete inspections before and after arrival
“We conduct thorough routine house inspections on all our rental properties before guests arrive to ensure they are clean and ready for occupancy,” suggests West Lake Properties. “We provide all the necessary supplies to make our guest’s stay comfortable, including turning on lights both inside and outside, adjusting the heating as needed, and if necessary, clearing snow from the walkway to the front door.
Additionally, our post-stay inspections ensure that homeowners can rest easy, knowing that their property is well taken care of. We make sure the house is damage-free then we secure the place by locking all windows and doors, turning the heat back to an acceptable temperature, and ensuring that all lights are off.”
29. Provide guests with snow essentials for their cars
Picture Properties Vacation Rentals says, “If your rental is in an area where it tends to snow, make sure you have someone nearby and available to plow your driveway. Have a snow shovel, windshield scraper, and ice melt granules readily available for your guests to use during their stay. Another helpful tip is to make sure your housekeeper keeps the heat at 55 degrees Fahrenheit when they leave after each cleaning in order to guarantee your pipes don’t freeze. Even better, install a smart wi-fi thermostat so you can set the temperature remotely with your phone. Not only will you save your pipes and your heat bill, you can turn the heat on in the house before your guests arrive so they are cozy and warm from the start of their vacation.”
30. Decorate for the holiday season
DoCo Vacations mentions, “Our approach to preparing our vacation rentals is centered around thoughtfully curated holiday decorations that align with the unique vibe of each rental property. Recognizing the significance of festive decor such as Christmas trees and making holiday plans. We ensure each unit is adorned in a way that not only resonates with its individual character but also sparks joy and a sense of holiday spirit among our guests, often leading to shareable moments for our guests through their social media profiles. This makes content for us to use in our own social media marketing.”
31. Add detail oriented comfort and a insightful welcome booklet
David and Lori Raun from Shasta Lakeshore Retreat says, “At our lake retreat, we focus on ensuring a comfortable and memorable winter experience for families in our ten vacation rental homes. We provide extra blankets for added comfort and meticulously inspect wood fireplaces, supplying ample dry oak for warmth. Outdoors, a firepit with a heat lamp encourages cozy gatherings. For group retreats, we offer board and dice games for serene winter evenings. Our gift basket includes rich hot chocolate, and our welcome materials detail ideal winter activities in the area to help guests make the most of their getaway. Our welcome book and website detail ideal winter activities in the area, ensuring guests make the most of their getaway.”
32. Prioritize group oriented configurations and comfort
Linda Ross from Stay WildFlower says “At Stay Wildflower, we meticulously prepare our vacation rental homes for the season, focusing on creating a festive atmosphere that caters to our guests’ unique desires. We prioritize practical winter comfort by ensuring essential amenities are in place, such as stocked Nespresso machines and well-prepped fireplaces and fire pits for chilly nights. To enhance togetherness during the holidays, we enable groups to book configurations that allow everyone to stay together under one roof. Our commitment to guest satisfaction includes immediate and responsive support, ensuring a seamless and enjoyable winter stay in the heart of Los Angeles.”
Courtesy of Stay WildFlower
33. Embrace new technology to automate management
Founder of Leasey.A, Juan Leal, says “From guest communication to maintenance challenges; technical difficulties can disrupt your business at any moment. These problems become especially difficult when hosting guests for the holidays.
If I could offer one piece of advice to property managers and rental investors, it would be to embrace new technology. Leveraging the power of an AI troubleshooting chat means you can offer support for your guests 24/7, even if your team is taking time off for the holidays. Using smart IoT devices to automate home amenities when the suite is vacant can dramatically reduce your operating costs during the winter months. IoT sensors can also help your team monitor the suite to detect potential issues like frozen pipes before they become major issues. In all, embracing new technology can lead to better guest experiences and fewer technical difficulties during the busy holiday season.”
34. Tricks to make the cold bearable for a more comfortable stay
Matt Floyd, Owner of Stay Classy Homes mentions, “As someone who grew up in Wisconsin and manages vacation rentals all around the country, here are a few recommendations as we head into the winter season:
- Keep your guests cozy by providing hot chocolate packets and investing in boot warmers for toasty gear the next morning.
- If you have a fireplace, consider partnering with a local firewood company for a discounted delivery. Stock extra fleece blankets for added warmth.
- Prioritize guest safety by ensuring someone regularly shovels and salts pathways to prevent injuries.
- Enhance energy efficiency with a smart thermostat, allowing remote temperature control to avoid high heating costs when the home is unoccupied.
35. Safety comes first
“As winter approaches, safety and comfort take center stage in our vacation rentals,” mentions WC Lodging. “We meticulously inspect properties, ensuring well-lit walkways and proactive measures against leaks. Our homes are equipped with safety essentials like handrails, emergency supplies, and functional heating systems.
Additionally, each Sonoma County house provides emergency contacts, including landline telephones, NOAA radios, and flashlights. In addition to clear safety instructions for rainy weather and heating appliances, our homes come equipped with extra blankets, pillows, puzzles, and games for an added touch of comfort and security during the winter season.”
Courtesy of WC Lodging
36. Do your own walk-through before guests arrive
“Being in close proximity to a ski area with colder temperatures, winter home preparation for incoming guests is paramount to our continued success,” says Mt. Baker Lodging. “Nothing is worse for guests than showing up to a dark, cold, and inadequately marked vacation home. With darkness upon us as early as 4:00PM, it’s important to be mindful that guests who are unfamiliar with the area need to be able to find their cabin or condo with a minimum of difficulty.
Once there, they need to be able to clearly see their way in while carrying their luggage, food, and personal items. Once inside, it’s always nice to be greeted by a warmed-up property. It’s worth taking the time to perform a walk-through on the day of guest arrival to make sure that all systems are in good working order, outside lights are on, and the heat is turned up. Technology is great, but nothing takes the place of seeing things with your own eyes. It’s the little details that create a great first impression, and keep our guests coming back year after year.”
37. Emphasis on prevention
“Winter is the time we conduct the majority of our preventive maintenance items on our properties,” says Manager Phil Caudle from Grand Welcome Newport Beach “This includes swapping fresh batteries in our electronic door locks, smoke detectors, tv remotes controls and garage openers. Exterior home and patio lights are checked. Parasols and umbrellas are tied down or removed. This is also a good time to check the wear and tear on patio furniture as well and order new covers before the rains arrive.”
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