A furnished Orlando house for the winter, by the month

A winter stay in Orlando, month by month

A season here usually starts with an email or a phone call in the fall. Tell us roughly when you want to arrive and how long you expect to stay, and we confirm the monthly rate, the deposit and the pet policy in writing before you commit to anything. Once you are ready, you sign a written monthly agreement, pay the first month, and arrival notes with the door code or the lockbox location land in your inbox a few days before you fly in. There is no year-long lease to break in the spring and no security deposit tangled up in a twelve-month contract: the agreement runs by the month, and it ends when your season does.

Once you are in the house, the routine is the one you would run at home. Groceries go in a full-size refrigerator, laundry runs in your own washer and dryer, and the car sits in a private driveway, so there is nowhere to circle looking for a space after a day at the springs or a walk around Lake Eola. Both homes below have kept the bones of the working-class Orlando streets they sit in: older single-story block houses with freshly renovated interiors. We say that plainly because the photos alone do not tell you what kind of street you are on.

If your plans firm up once you are here, the agreement moves with you. A season that was going to run through February and stretches into April is a short email, provided the house is not already promised to the next guest. If the season should end a few weeks early instead, notice is straightforward and spelled out in the agreement before you pay anything. Either way, nothing about the arrangement changes once you are in the house: same rate, same house, same key.

Two homes for a winter season

Of the thirteen houses in the portfolio, two are set up the way a snowbird actually uses a house: room to spread out for months, a private driveway for a car that is going to sit for a season, and a yard instead of a shared hallway.

Northwest Orlando

Lockhart / Rosemont

WinterPark Home

3 bd 1 ba Sleeps 8

13 min downtown · 10 min AdventHealth · 26 min Universal

Travel Nurse & MedicalRelocation & Long-Stay

South of Downtown

Holden Heights

Fruit Tree Home

3 bd 2 ba Sleeps 10

6 min downtown · 5 min ORMC · 13 min Universal

Travel Nurse & MedicalInsurance & Displacement

The Katherine House in Lockhart is the quieter of the two: a three-bedroom, one-bathroom block home on a residential street with a screened porch, patio seating, a grill, and a private concrete driveway. The kitchen is stocked with cookware, dishes and a coffee maker, the shower is a tiled walk-in, and a community park with a playground and courts sits a short walk away, useful if grandchildren fly down to join you over the holidays. It sleeps up to eight across its three bedrooms. The exterior roof trim shows some peeling paint and the lawn is patchy in spots; the inside was freshly renovated, and the porch and the driveway are the parts that matter for a long stay.

The 25th Street House in Holden Heights sits closer to the middle of the city: a three-bedroom, two-bathroom bungalow with fruit trees in the fenced backyard, a screened front porch, and full-size laundry on site. It sleeps up to ten across three bedrooms, one with a daybed, which suits a couple who wants the spare room to double as an office most of the season and a guest room when someone visits. The laundry sits in an unfinished utility area off the porch, next to the water heater, worth knowing before you book. Both homes keep their monthly rate, deposit and pet policy confirmed in writing once you tell us your dates; several homes across the portfolio accept pets, so tell us about yours and we will confirm whether it fits before you commit.

Reaching Winter Park, downtown and the springs

Winter is the season Central Florida makes its case against the coasts, and the case gets stronger the closer you can get to more than one thing at once. Both homes sit on the portfolio's north side, in Lockhart and Holden Heights, which puts Winter Park, downtown Orlando and Wekiwa Springs State Park all within a single afternoon's driving.

WinterPark Home is the closer of the two to Winter Park, about 8 minutes by road, which matters if Park Avenue's shops or Rollins College are part of why you wanted this side of the state. Fruit Tree Home is about 11 minutes from Winter Park and closer to everything south of it: about 6 minutes to downtown Orlando and 8 to Lake Eola Park, against 13 and 14 minutes from WinterPark Home.

The map below places every home in its true compass direction from Winter Park, with the distance from the centre standing in for drive minutes rather than miles.

Wekiwa Springs State Park, a clear spring that holds 72 degrees year round with swimming, snorkeling and canoe or kayak rental at the concession, is about 20 minutes from WinterPark Home and 28 from Fruit Tree Home, a reasonable outing on a mild afternoon partway through the season. Here is how all three destinations line up against the wider portfolio, useful if you are weighing which part of the city to base a season in.

Typical road-routing times without traffic; Orlando rush hours add to the longer routes.

What's in the house for a season

Every home comes with the basics already confirmed in writing when you book: furniture, beds and linens, a stocked kitchen, a washer and dryer, Wi-Fi and private parking.

Exact inclusions vary a little by home and are confirmed in writing when you book.

For a stay measured in months, the small things matter more than they do on a week's vacation. Both homes have a ceiling fan in the living room, useful on the mild, still-warm afternoons Central Florida gets even in January, and the kitchen in each is comfortable enough to cook a full holiday dinner in. WinterPark Home's screened porch, with patio seating and a grill, gives you an outdoor room that stays usable through a Florida winter in a way a snowbound porch up north does not, and Fruit Tree Home's fenced backyard, with fruit trees, does the same job without the screen.

Wi-Fi is live from the day you arrive, which matters if part of your season is spent video-calling family back home or managing accounts from a laptop at the kitchen table. Both kitchens already have cookware and dishes on hand, so the first grocery run can go straight to food instead of pots and pans. Parking is a private concrete driveway at both homes: no permit, no shared lot, and nowhere to hunt for a spot after an afternoon at the springs.

Booking a season and paying once

A season is booked the same way any of our monthly stays are: you tell us your dates and which home you are leaning toward, we confirm the monthly rate, the deposit and the pet policy in writing, and you sign a written monthly agreement before the first payment is due. There is no separate seasonal package to negotiate; the agreement is written for however many months your season runs, four in a typical November-through-March stay or fewer if that is what you need.

Booking the house directly with us means one clear monthly rate for the whole house. The rate is for the whole house, and the receipts are itemized by month, useful if you track winter-season costs separately from the rest of the year or reconcile them with a family member back home. If a short visit before your season starts, or a quick trip back in the spring, makes more sense as a few nights than a signed monthly agreement, both homes also take nightly and weekly bookings through their Airbnb and Vrbo listings.

Extending is the part that tends to matter most for snowbirds, because plans made in October often loosen once you are here. If March turns into April, tell us as soon as you know and we extend the agreement by the month at the same terms, provided the house is not already committed to the next guest. If it is, we say so early and point you to whichever of our other homes is open, so you are not left working it out the week before you were due to leave.

Living near Lockhart, Holden Heights and Winter Park

WinterPark Home sits in the Lockhart and Rosemont cluster, where the closest full grocery options are the Walmart Supercenter on West Princeton Street and Presidente Supermarket on North Pine Hills Road, a Latin grocer with a cafeteria and juice counter built in. A few blocks south on West Colonial Drive, Caribbean Supercenter has anchored the area's Caribbean shopping for about forty years, and it is one of the more useful corners in the city to cook a season's worth of meals from. Barnett Park, a 159-acre county park on West Colonial Drive, has a free splash pad that runs through the warm months, playgrounds, walking trails, disc golf and a recreation center with a workout room, all free to use.

Fruit Tree Home sits in the downtown and close-in cluster, closer to Lake Eola Park, whose roughly one-mile sidewalk loop and Sunday farmers market from 10 a.m. to 3 p.m. are easy to fold into a weekly routine across a whole season. The compact Publix at The Paramount on Lake Eola is the nearest downtown grocery, and College Park's Edgewater Drive, a short drive north, is where the sit-down cafes are: Foxtail Coffee for a laptop-friendly room, Tartine for a small French cafe with pastries, and Adriatico Trattoria or Zeytin for a proper dinner out without crossing the city.

Winter Park FL Downtown HD01 · Ebyabe · CC BY-SA 3.0 · resized from 3264x2448

Winter Park itself, closest to WinterPark Home, is worth the short drive on its own terms: Park Avenue's shops and restaurants, and Rollins College, give a season here somewhere ordinary to walk, away from the theme parks. Full Sail University, also in Winter Park, sits nearby too, one more reason this side of the metro stays busy through the winter months.

Pharmacies are easy to find near either home: CVS and Walgreens along Silver Star Road and Pine Hills Road serve WinterPark Home's side of town, and downtown's Publix pharmacy at Lake Eola, a few blocks from Fruit Tree Home, is not far behind. For a gym membership that covers the season, a 24-hour Planet Fitness sits on Silver Star Road toward Ocoee, and the Downtown Orlando YMCA on North Mills Avenue, with its pools and class schedule, is the closer option from Holden Heights.

What guests said about WinterPark Home

The reviews below are real, pulled verbatim from WinterPark Home's own Airbnb listing, with the reviewer's name and the month they stayed; the home carries 59 reviews at a 4.79 rating.

Natalie, who stayed in October 2024, put it plainly: "The house met our needs for the time we stayed. The owner was fantastic to work with." That is close to what a season needs from a house: an owner who answers the phone when something needs attention, and a place set up to work for months at a stretch. Fruit Tree Home carries its own set of reviews and a 4.83 rating across 142 stays, the most of any home in the portfolio, viewable on our reviews page alongside every other home's.

Before you book a season, a checklist

The snowbirds who have the smoothest move-ins tend to sort these out before they inquire.

• Your dates, both ends. Tell us when you want to arrive and when you expect to leave, even if the back end is a guess; it is easier to extend a season than to shorten one that was booked too long.
• Who is coming, and when. A spouse for the whole season, family for a week over the holidays, a pet. WinterPark Home sleeps up to eight and Fruit Tree Home up to ten, and pets are confirmed in writing before you commit.
• Which cluster matters more to you. WinterPark Home sits closer to Winter Park and AdventHealth's northern campuses; Fruit Tree Home sits closer to downtown, Lake Eola Park and Orlando Health.
• A car, and a transponder. Both homes have a private driveway, but you will want a car for the season; SR-408, the expressway along this side of the city, is tolled by transponder or plate, so a SunPass or E-PASS is worth having for a stay this long.
• The plain parts. Older block homes, one bathroom at WinterPark Home, and an unfinished-feeling laundry area at Fruit Tree Home. We describe them as they are so nothing surprises you in November.

Send us that list with your dates and we usually come back the same day with a rate, real photos, and the drive time from the home to wherever in Central Florida you plan to spend your winter.

More reading for a season in Orlando

Two of our guides go further into the questions that follow this one: why some snowbirds choose the middle of Florida over the coasts, and how each of the thirteen homes fits a different kind of stay.

Seasonal · 5 min

Spending the Winter in Orlando

Why some snowbirds pick the middle of Florida over the coasts, what a winter here is like, and how a monthly house works for the season.

Read →

The Homes · 6 min

Which Libema Home Is Right for You

All thirteen homes matched to the stays people actually book: a solo nurse, a couple, a family of five, a crew, a reunion, a game weekend, a hospital assignment.

Read →

If your season overlaps with visiting family who need to be near a hospital, our page on housing for patients' families covers the same homes from that angle, and the neighborhood pages for Lockhart, Rosemont and Holden Heights lay out the daily details for each cluster in full.